Patent Application
20120277423
The present invention relates to a compound having transglutaminase-inhibiting activity or an inhibitor of protein crosslinking and to the use of the same.
More specifically, the present invention relates to a compound having transglutaminase-inhibiting activity, which is a ketone or alcohol, especially a ketone, having a particular structure, to an inhibitor of protein crosslinking and/or an intracellular calcium modulator, and to a composition for preventing or treating protein-crosslinking causative diseases such as Alzheimer's disease, Huntington's disease, Parkinson's disease, Celiac disease, cataract, mad cow disease, congenital lamellar ichthyosis, congenital hemostatic disorder, liver disorder, autoimmune disease, and cerebral infarction.
Calcium is well known to play various and important roles in living organisms and cells. In the past, the present inventors discovered that 2-APB (2-aminoethyl diphenyl borinate) acts to modulate the intracellular calcium concentration (Non-Patent Literature 1), and then synthesized about 500 different boron compounds analogous to 2-APB and examined calcium concentration modulating activities of these compounds (Patent Literatures 1 to 4). As a result, it was revealed that these compounds function to modulate an intracellular calcium concentration associated with SOCE (store operated calcium entry) or IICR (IP3 induced calcium release). In addition, it was found that some of the compounds have transglutaminase-inhibiting activities, in addition to the above-mentioned activities.
It has been revealed that abnormal crosslinking reactions of certain proteins cause intractable diseases such as Alzheimer's disease, Huntington's disease, Parkinson's disease, Celiac disease, cataract, mad cow disease, congenital lamellar ichthyosis, and congenital hemostatic disorder (Non-Patent Literatures 2 to 4). In particular, an enzyme that is thought to be involved in abnormal protein crosslinking reactions is transglutaminase.
Transglutaminase is an enzyme that is activated in the presence of calcium. Recently, it has been known that transglutaminase is involved in the development of neurological diseases such as Alzheimer's disease, Parkinson's disease, and Huntington's disease. Thus, transglutaminase inhibitors are thought to be effective drugs for treatment of such diseases (Non-Patent Literatures 5 and 6).
The main reaction of the abnormal protein crosslinking is a reaction in which isopeptide bonds are formed from the amide group of glutamine and the amino group of lysine of a protein through deammoniation. The mechanism revealing that inhibitors of the enzyme capable of inducing such reaction (i.e., transglutaminase) would be effective for treatment of the aforementioned diseases or the like has been clarified (Non-Patent Literature 7). Based on these findings, there are increasing researches to develop transglutaminase inhibitors as therapeutic drugs for diseases such as Alzheimer's disease, Huntington's disease, Parkinson's disease, Celiac disease, cataract, mad cow disease, congenital lamellar ichthyosis, congenital hemostatic disorder, liver disorder, autoimmune disease, and cerebral infarction (Non-Patent Literatures 8 to 13).
An object of the present invention is to produce compounds having the action of modulating an intracellular calcium concentration, modulators of transglutaminase activity, and compounds capable of modulating a protein crosslinking reaction. Another object of the present invention is to develop drugs for preventing and/or treating diseases caused by abnormal protein crosslinking.
In order to achieve the above-mentioned objects, the present inventors attempted to find compounds having the above-mentioned action other than boron compounds previously developed by the present inventors. As a result, the present inventors have now found that ketone compounds having particular structures have the action significantly superior to the boron compounds. This led to the completion of the present invention. It was revealed that such ketone compounds have transglutaminase-inhibiting activities, and that they include compounds that substantially do not inhibit SOCE but strongly inhibit IICR, and compounds inhibiting IICR more strongly than SOCE.
The present invention has the features as described below.
In a first aspect, the present invention provides a ketone compound having transglutaminase-inhibiting activity, which is represented by Formula (1), (2), or (3):
wherein R1 is a substituted or unsubstituted aryl or heterocyclyl group, R2, R3, and R4 are hydrogen atoms, n is 2, X is halogen, R5 and R6 independently represent a hydrogen atom or a substituted or unsubstituted C1-C10 alkyl, aryl, or aralkyl group, wherein R5 and R6 are not hydrogen atoms at the same time, or R5 and R6 may be taken together to form a saturated or unsaturated and substituted or unsubstituted heterocyclyl group containing a nitrogen atom (N).
In one embodiment of the present invention, R1 is a substituted or unsubstituted phenyl, naphthyl, fluorenyl, benzothienyl, pyridyl, pyrazinyl, furyl, thienyl, pyrrolyl, thiazolyl, ferrocenyl, morpholino, or 6- to 7-membered cyclic lactam group.
In another embodiment of the present invention, R5 or R6 is a substituted or unsubstituted benzyl or C1-C6 alkyl group.
In another embodiment of the present invention, a heterocyclyl group formed from R5 and R6 is a substituted or unsubstituted piperadino, piperidino, or pyrrolidino group.
In another embodiment of the present invention, a substituent on R1 is one or more C1-C4 alkyl, halogen, cyano, hydroxy, C1-C4 alkoxy, or substituted or unsubstituted phenyl, phenoxy, or phenylthio groups.
In another embodiment of the present invention, a substituent on R5 or R6 is one or more substituted or unsubstituted C1-C10 alkyl, halogen, cyano, hydroxy, C1-C4 alkoxy, C1-C4 alkylcarbonyl, C1-C4 alkylcarbonyloxy, disulfide, thiol, amino, substituted or unsubstituted mono-C1-C10 alkylamino, substituted or unsubstituted di-C1-C10 alkylamino, carbonyl, substituted or unsubstituted phenyl or phenyl-C1-C4 alkyl, or substituted or unsubstituted aryl or heterocyclyl groups.
In another embodiment of the present invention, the ketone compound represented by Formula (1) is selected from the group consisting of the following compounds (where the numerals in parentheses represent compound ID numbers).
In another embodiment of the present invention, the ketone compound represented by Formula (2) is selected from the group consisting of the following compounds, (where the numerals in parentheses represent compound ID numbers).
In another embodiment of the present invention, the ketone compound represented by Formula (3) is selected from the group consisting of the following compounds (where the numerals in parentheses represent compound ID numbers).
In another embodiment of the present invention, the ketone compound further has IICR-inhibiting activity higher than SOCE-inhibiting activity.
Where the SOCE activity is inhibited, store operated calcium entry (SOCE) is inhibited. Meanwhile, where the IICR activity is inhibited, IP3 induced calcium release (IICR) is inhibited. When a compound has an IICR-inhibiting activity higher than SOCE-inhibiting activity, it means that the compound can control IICR and SOCE such that the amount of Ca2+ released into the endoplasmic reticulum becomes greater than the amount of Ca2+ released from the endoplasmic reticulum. In such case, it is predicted that the Ca2+ concentration in cytoplasm surrounding the endoplasmic reticulum would transiently decrease. Since transglutaminase (TG) activity is changed in a Ca2+-concentration-dependent manner, a decrease in Ca2+ concentration would cause inhibition of TG activity. Therefore, it is thought that a compound that has a high TG-inhibiting activity and also has an IICR-inhibiting activity higher than SOCE-inhibiting activity would be able to inhibit TG with good efficiency. When the IICR-inhibiting activity is compared with the SOCE-inhibiting activity at a compound concentration that allows 50% inhibition, the IICR-inhibiting activity would be, for example, at least 3 times, preferably at least 5 times, more preferably at least 10 times, further preferably at least 50 times as strong as the SOCE-inhibiting activity.
In another embodiment of the present invention, a ketone compound that has an IICR-inhibiting activity higher than SOCE-inhibiting activity is selected from the group consisting of the following compounds (where the numerals in parentheses represent compound ID numbers).
In a second aspect, the present invention provides a transglutaminase activity inhibitor, which comprises at least one member selected from the group consisting of the compounds represented by any of Formulae (1) to (3) and the aforementioned specific compounds.
In a third aspect, the present invention provides an inhibitor of protein crosslinking, which comprises at least one of the compounds represented by any of Formulae (1) to (3) and the aforementioned specific compounds.
In a forth aspect, the present invention provides a calcium concentration modulator, which comprises at least one of the compounds represented by any of Formulae (1) to (3) and the aforementioned specific compounds.
In a fifth aspect, the present invention provides a composition for prevention or treatment of a protein-crosslinking causative disease, which comprises at least one of the compounds represented by any of Formulae (1) to (3) and the aforementioned specific compounds.
In the above aspects of the present invention, the protein-crosslinking causative disease is selected from the group consisting of Alzheimer's disease, Huntington's disease, Parkinson's disease, Celiac disease, cataract, mad cow disease, congenital lamellar ichthyosis, congenital hemostatic disorder, liver disorder, autoimmune disease, and cerebral infarction.
This description includes all or part of the contents as disclosed in the description and/or drawings of Japanese Patent Application No. 2009-255518, from which the present application claims the pripority.
The compounds of the present invention have the action of modulating an intracellular calcium concentration (SOCE and/or IICR) or the action of inhibiting a transglutaminase (TG) activity or a protein crosslinking reaction. In addition, it has now been found that these compounds include therapeutically useful compounds that strongly exhibit the TG-activity-inhibiting action (i.e. the protein-crosslinking-inhibiting action) and also strongly exhibit an IICR-inhibiting activity but almost no SOCE-inhibiting activity. Since the compounds of the present invention have such properties, they are useful for prevention or treatment of diseases caused by abnormal protein crosslinking (e.g., Alzheimer's disease, Huntington's disease, Parkinson's disease, Celiac disease, cataract, mad cow disease, congenital lamellar ichthyosis, congenital hemostatic disorder, liver disorder, autoimmune disease, and cerebral infarction).
The present invention provides a ketone compound having transglutaminase-inhibiting activity represented by Formula (1), (2), or (3) above. Such compound has a protein-crosslinking-inhibiting action and thus it can be effectively used for prevention or treatment of a disease caused by an abnormal crosslinking reaction of a certain protein.
In any Formula shown above, R1 is a substituted or unsubstituted C1-C20 alkyl, aryl, or heterocyclyl group, R2, R3, R4, R5, and R6 independently represent a hydrogen atom or a substituted or unsubstituted C1-C10 alkyl, aryl, or aralkyl group, wherein R5 and R6 are not hydrogen atoms at the same time, or R5 and R6 may be taken together to form a saturated or unsaturated and substituted or unsubstituted heterocyclyl group containing a nitrogen atom (N), X is halogen or NR5R6 (where R5 and R6 have the same meanings as defined above), and n is an integer of 2 to 4, preferably 2.
A preferable example of the compound is a ketone compound having transglutaminase-inhibiting activity of Formula (1), (2) or (3), wherein R1 is a substituted or unsubstituted aryl or heterocyclyl group, R2, R3, and R4 are hydrogen atoms, n is 2, X is halogen, R5 and R6 independently represent a hydrogen atom or a substituted or unsubstituted C1-C10 alkyl, aryl, or aralkyl group, wherein R5 and R6 are not hydrogen atoms at the same time, or R5 and R6 may be taken together to form a saturated or unsaturated and substituted or unsubstituted heterocyclyl group containing a nitrogen atom (N).
The alkyl group is a substituted or unsubstituted C1-C20, preferably C1-C10, more preferably C1-C6, such as C1-C4, linear, branched, or cyclic alkyl group. Examples thereof include methyl, ethyl, n- or iso-propyl, n-, iso- or tert-butyl, n-pentyl, n-hexyl, cyclopentyl, cyclohexyl, and adamantyl.
The aryl group is a substituted or unsubstituted monocyclic or (condensed) polycyclic (preferably bicyclic or tricyclic) aromatic group. Examples thereof include substituted or unsubstituted phenyl, naphthyl, and anthracenyl. Examples of substituted phenyl include ethylenedioxyphenyl, diphenyl, phenoxy-phenyl, benzyl-phenyl, and phenylthio-phenyl.
The aralkyl group is an arylalkyl group. Examples thereof include substituted or unsubstituted phenylalkyl such as benzyl, phenylethyl, and phenylpropyl.
The heterocyclyl group is a cyclic group containing 1 atom or 2 or more different atoms (such as N, O, or S other than C) on its ring. It may be a substituted or unsubstituted and saturated or unsaturated monocyclic heterocyclyl group or condensed heterocyclyl group. Examples thereof include, but are not limited to, pyridyl, pyrimidyl, quinolyl, isoquinolyl, furyl, pyrazyl, pyrazinyl, pyrazolyl, pyrimidyl, pyridazinyl, imidazolyl, thiazolyl, isothiazolyl, imidazolyl, oxazolyl, isooxazolyl, triazolyl, thienyl, pyrrolyl, indolyl, carbazolyl, indazolyl, pyrrolidinyl, pyrrolinyl, imidazolidinyl, pyrazolidinyl, pyrazolinyl, piperazyl, piperidyl, piperazinyl, indolinyl, morpholinyl, benzofuryl, benzothienyl, lactone, lactam, and ferrocenyl.
The halogen is a fluorine atom, a bromine atom, a chlorine atom, or an iodine atom.
The position of the above substituents is not particularly limited.
Examples of the substituents include one or more C1-C10 alkyl (e.g., methyl, ethyl, n- or iso-propyl, or n-, iso- or tert-butyl), C2-C10 alkenyl (e.g., ethenyl or propenyl), C2-C10 alkynyl, halogen (e.g., fluorine, bromine, chlorine, or iodine), C1-C4 alkoxy (e.g., methoxy, ethoxy, or n- or iso-propoxy), methylenedioxy, ethylenedioxy, C1-C4 alkylthio (e.g., methylthio or ethylthio), C1-C4 alkylsulfonyl (e.g., mesyl or ethylsulfonyl), sulfamoyl, carboxy, C1-C4 alkoxycarbonyl (e.g., methoxycarbonyl or ethoxycarbonyl), C1-C4 alkylcarbonyloxy (e.g., acetoxy or ethylcarbonyloxy), hydroxy, mercapto, alkylthio, amide, acetamide, carbonyl (—C(═O)—), amino, mono- or di-C1-C4 alkylamino (e.g., methylamino, dimethylamino, ethylamino, or diethylamino), hydroxyalkylamino, nitro, cyano, isocyanato, thiocyanato, cycloalkyl (e.g., cyclohexyl or cyclopentyl), disulfide (—S—S—), —NH—, and aryl or heterocyclyl groups that have the same meanings as defined above. However, the substituents are not limited to such examples as long as the compound is imparted with transglutaminase-inhibiting activity.
In an embodiment of the present invention, preferably R1 is a substituted or unsubstituted phenyl, naphthyl, fluorenyl, benzothienyl, pyridyl, pyrazinyl, furyl, thienyl, pyrrolyl, thiazolyl, ferrocenyl, morpholino, or 6- to 7-membered cyclic lactam group.
In another embodiment of the present invention, preferably R5 or R6 is a substituted or unsubstituted benzyl or C1-C6 alkyl group.
In another embodiment of the present invention, a preferable heterocyclyl group formed from R5 and R6 is a substituted or unsubstituted piperadino, piperidino, or pyrrolidino group.
In another embodiment of the present invention, examples of a preferable substituent on R1 include one or more C1-C4 alkyl, halogen, cyano, hydroxy, C1-C4 alkoxy, or substituted or unsubstituted phenyl, phenoxy, or phenylthio groups.
In another embodiment of the present invention, examples of a preferable substituent on R5 or R6 include one or more substituted or unsubstituted C1-C10 alkyl, halogen, cyano, hydroxy, C1-C4 alkoxy, C1-C4 alkylcarbonyl, C1-C4 alkylcarbonyloxy, disulfide, thiol, amino, substituted or unsubstituted mono-C1-C10 alkylamino, substituted or unsubstituted di-C1-C10 alkylamino, carbonyl, substituted or unsubstituted phenyl or phenyl-C1-C4 alkyl, or substituted or unsubstituted aryl or heterocyclyl groups.
Specifically, examples of the compounds of the present invention include, but are not limited to, the following compounds (where the numerals in parentheses represent compound ID numbers).
The above compounds, and in particular, the compounds represented by Formula (1), include compounds that have high transglutaminase-inhibiting activities. Many such compounds have an acryloyl (—CO—CH═CH2) group and a substituted or unsubstituted aromatic group such as phenyl, naphthalene, or diphenylmethane. Examples of such compounds include the following compounds (where the numerals in parentheses represent compound ID numbers).
Further preferable examples of the compounds of Formula (1) include the following compounds.
Alternatively, other examples of the compound of the present invention include the following compounds represented by Formula (2), wherein X is halogen and n is 2 (where the numerals in parentheses represent compound ID numbers).
Further preferable examples of the compounds of Formula (2) include the following compounds.
Alternatively, examples of the compounds of the present invention include the following compounds represented by Formula (3) (where the numerals in parentheses represent compound ID numbers).
Preferable examples of the compound of Formula (3) are described below (where the numerals in parentheses represent compound ID numbers).
In addition, the compounds shown in table 1 below are characterized in that they strongly exhibit a TG-activity-inhibiting action or protein-crosslinking-inhibiting action and also strongly exhibit an IICR-inhibiting activity but almost no SOCE-inhibiting activity.
In addition to the compounds shown in table 1, the following compounds similarly exhibit an excellent activity (where the numerals in parentheses represent compound ID numbers). These compounds also strongly exhibit a TG-activity-inhibiting action or protein-crosslinking-inhibiting action and have an IICR-inhibiting activity higher than SOCE-inhibiting activity.
The compound of the present invention can be obtained by synthesizing compounds using, for example, a variety of reactions described in the Examples below, purifying the compounds, examining the bioactivity (e.g., transglutaminase-inhibiting activity) levels of the compounds, and selecting an optimum compound.
The compounds of the present invention can be produced by the methods described in the following: H. Dannenberg et al., Zur Darstellung von 1,5-Benzindan, Chemiche Ber. (1955) 88:1405; F. Mayer et al., Uber eine Synthese von Indanen, Ber. (1922) 60:2279; A. E. Vanstone et al., A Covenient Preparation of Viny Ketones, J. Chem. Soc. (C) (1966) 1972; F. Golemba. et al., Polymers of Phenyl Vinyl Ketones, Macromoleculeles (1972) 5:212; and WO 2007/136790, for example.
Purification can be carried out by techniques generally used in the art such as salting-out, extraction, evaporation, distillation, crystallization, and chromatography (e.g., silica gel column chromatography, ion-exchange chromatography, hydrophobic interaction chromatography, size-exclusion chromatography, HPLC, gas chromatography, or thin-layer chromatography). In addition, the obtained compounds can be analyzed by NMR, IR, Mass spectrometry, element analysis, or the like.
The above compounds can be synthesized by Friedel-Crafts reactions (I) and (II) and Grignard reaction (III) with the reaction schemes shown in Reaction formulae (I) to (VIII) below. Ketone (1) can be obtained via chromic acid oxidation of alcohol (4) obtained through Grignard reaction (III) (Reaction formula (IV)). Compound (3) can be obtained through Michael addition of amine and ketone (1) which is an acryloyl compound (Reaction formula (V)). Compound (5) can be obtained by allowing paraformaldehyde and amine to react with ketone (8) (Reaction formula (VI); Mannnich Reaction (Arend M et al., Angew. Chem. Int. Ed (1998) 37: 1044)). When compound (5) is in the acidic condition, a reverse reaction of the Michael reaction occurs to give compound (6) (Reaction formula (VII)). In addition, compound (7) can be obtained by reacting halogenated ketone (compound (2) (X═Cl)) with amine (Reaction formula (VIII)).
(wherein R1 to R6, X, and n have the same meanings as defined above).
The present inventors have now found that compound (1) comprising a double bond conjugated with the carbonyl of the ketone has a strong transglutaminase activity. Further, the present inventors have now found that compound (3), which is synthesized by allowing the compound to react with amine via the Michael addition reaction, also has an activity similar to that of compound (1). Accordingly, the present inventors assayed the obtained compounds for both calcium concentration modulating action (i.e., SOCE or IICR) and TG (transglutaminase)-activity-inhibiting action, synthesized compounds having preferable activity, and selected preferable R1 to R6, X, and n. As a result, it has now been found that compound (5) obtained using, as a raw material, compound (8), such as acetylpyridine, acetylfuran, acetylthiophene, or acetylpyrazine, has the most preferable TG activity. Further, the present inventors have now found the compounds exemplified above, which are characterized in that they have low levels of or no SOCE-inhibiting activity but high levels of IICR-inhibiting activity, among the above-described compounds.
The compounds of the present invention have TG-activity-inhibiting action, i.e., protein-crosslinking-inhibiting action. As such, they can be used as prophylactic/therapeutic drugs or pharmaceutical compositions for preventing or treating diseases caused by abnormal protein crosslinking reactions. Examples of such diseases include Alzheimer's disease, Huntington's disease, Parkinson's disease, Celiac disease, cataract, mad cow disease, congenital lamellar ichthyosis, congenital hemostatic disorder, liver disorder, autoimmune disease, and cerebral infarction. In addition, the relationship between the diseases exemplified above and abnormal protein crosslinking is as described in “Background Art” above.
In addition, as described above, the compounds of the present invention include compounds characterized in that they have TG-activity-inhibiting action or protein-crosslinking-inhibiting action and have low levels of SOCE-inhibiting activity (and thus do not significantly influence the SOCE function) but high levels of IICR-inhibiting activity. There are known diseases associated with an increase in intracellular calcium concentration. Examples of such diseases include Alzheimer's disease, platelet aggregation, ischemic heart or brain diseases, immunodeficiency, allergic diseases, bronchial asthma, hypertension, cerebral vasoconstriction, a variety of kidney diseases, pancreatitis, autoimmune disease, multiple sclerosis (MS), Crohn's disease, and Sjögren's syndrome. Examples of known diseases caused in connection with the IICR function (i.e., the induction of calcium ion release from calcium ion pools in a cell) include ischemic diseases of the heart or brain, hypertension, cerebral vasoconstriction, and Alzheimer's disease (JP Patent Publication (Kokai) No. 2009-184988 A). The compounds of the present invention can be used as drugs for treating or preventing such diseases.
As used herein, the term “protein crosslinking” refers to a situation in which a new intramolecular or intermolecular protein chain bond (e.g. a covalent bond, ion bond, coordination bond, or hydrogen bond) is formed for crosslinking.
In addition, it is known that when an abnormal protein crosslinking reaction takes place in the brain so as to result in insoluble protein formation or protein aggregation, neurodegenerative diseases such as Alzheimer's disease, Huntington's disease, and Parkinson's disease are developed.
Transglutaminase is an enzyme that is involved in protein crosslinking in the cases of the above diseases. As such, transglutaminase inhibitors are effective for prevention or treatment of the diseases.
According to the present invention, the enzyme-inhibiting action of transglutaminase (TGase) can be determined by assaying enzyme activity using an optionally modified version of the method of Lorand et al. (Lorand, L. et al. (1971) Anal Biochem. 1971 November 44 (1):221-31). Specifically, the methods described in the Examples below can be used.
Alternatively, the therapeutic effects of the compounds of the present invention can be confirmed by administering each of the compounds of the present invention to model animals (e.g. mice) with diseases such as Alzheimer's disease, Huntington's disease, and Parkinson's disease and observing alleviation of the symptoms. Examples of known model animals include Huntington's disease model mice (J Neurol Sci, 231: 57-66 (Apr. 15, 2005)), Alzheimer's disease model mice (J. Clin. Invest., 116 (3): 825-832 (2006)), and Parkinson's disease model mice (PLoS Biol. 3 (8): e303 (2005 August)).
One or more compounds of the present invention (i.e., active substances or active ingredients) formulated in the oral or parenteral dosage form can be systemically or locally administered to subjects (i.e., mammals including humans, and preferably humans). Examples of parenteral administration include intravenous administration, intraarterial administration, intramuscular administration, subcutaneous administration, intradermal administration, intraperitoneal administration, intrarectal administration, intradural administration, intravaginal administration, transmucosal administration, intracerebral/transdural administration, and intraocular administration.
The administration dose would vary depending on the type of compound to be administered, subject's age, sex, weight, and symptoms, expected therapeutic effects, administration methods, and the like. However, in general, the dose for an adult (with a body weight of about 60 kg) is, for example, 10 μg to 1,000 mg per oral administration once or several times per day. Alternatively, it is, for example, 1 μg to 100 mg per oral administration once or several times per day.
Examples of the formulations of the compounds of the present invention include, but are not limited to: tablets, pills, suspensions, solutions, capsules, syrups, elixirs, granules, and powders for oral administration; injections, drugs for external use, suppositories, solutions for external use, ointments, liniments, inhalation, and spray for parenteral administration; and pessaries for intravaginal administration.
The above formulation can comprise a pharmaceutically acceptable carrier (e.g., an excipient or a diluent) and an additive, in combination with the compound of the present invention used as an active ingredient.
Examples of excipients include lactose, mannitol, glucose, microcrystalline cellulose, and starch.
Examples of an additive include a binder (e.g., hydroxypropyl cellulose, polyvinyl pyrrolidone, or magnesium aluminometasilicate), a disintegrant (e.g., calcium carboxymethyl cellulose), a lubricant (e.g., magnesium stearate), a stabilizer (e.g., an amino acid or a sugar), and a solubilizer (e.g., glutamic acid or aspartic acid).
The formulation of the present invention may be coated with a coating agent (e.g. sucrose, gelatin, hydroxypropyl cellulose, or hydroxypropyl methylcellulose phthalate) or it may be coated with at least two layers. As a result of such coating, the formulation of the present invention can be formed into a controlled-release formulation, an enteric formulation, or the like. Further, it may be formed into capsules made of an bioabsorbable material such as gelatin (i.e., soft or hard gelatin).
A solution for oral administration is prepared by dissolving, suspending, or emulsifying at least one active substance in a generally used diluent (e.g., purified water, ethanol, buffer, Ringer's solution, or a mixture thereof). The thus prepared solution may contain a wetting agent, a suspending agent, an emulsifier, a stabilizer, a sweetening agent, a flavor, a fragrance, a preservative, a buffering agent, and the like.
Examples of injections for parenteral administration include solutions, suspensions, emulsions, and injections prepared by dissolving or suspending in a solvent upon use. An injection is prepared by dissolving, suspending, or emulsifying at least one active substance in a solvent. Examples of a solvent include distilled water for injection, physiological saline, vegetable oil, propylene glycol, polyethylene glycol, alcohol such as ethanol, and combinations thereof. Such injection may comprise a stabilizer (e.g., an amino acid such as lysine or methionine, or a sugar such as trehalose), a solubilizer (e.g., glutamic acid, aspartic acid, or polysorbate 80 (registered trademark)), a suspending agent, an emulsifier, a soothing agent, a buffer, a preservative, and the like. The prepared injection is sterilized in the final production step or produced/formulated by an aseptic technique. In addition, it is possible to produce a sterile solid agent such as a freeze-dried product and dissolve the product in sterilized or sterile distilled water for injection, or in a different solvent, before use.
A spray formulation may comprise a stabilizer such as sodium bisulfite and a buffering agent that can impart isotonicity, such as an isotonic agent (e.g., sodium chloride, sodium citrate, or citric acid), in addition to a generally used diluent.
The present invention will hereafter be described in more detail with reference to the following examples. It is contemplated, however, that the technical scope of the present invention is not limited to the examples.
The extracellular fluid (i.e., medium) of cultured Chinese hamster ovary (CHO) cells was replaced by BSS containing no calcium. One minute later, a test compound was added. Two minutes later, 1 μM thapsigargin was added to cause depletion of the intracellular calcium store. Nine minutes later, calcium chloride (final concentration: 2 mM) was added to the extracellular fluid. The SOCE-inhibiting action levels at different compound concentrations after the addition of calcium chloride were determined as the percentage of inhibition (%) by evaluating the influence of the compound on the degree of increase in the intracellular calcium concentration.
The extracellular fluid (i.e., medium) of cultured CHO cells was replaced by BSS containing calcium. One minute later, a test compound was added. Two minutes later, 10 μM ATP was added. The IICR-inhibiting action levels at different compound concentrations after the addition of ATP were determined as the percentage of inhibition (%) by evaluating the influence of the compound on the degree of increase in the intracellular calcium concentration.
Inhibition of TG enzyme was determined by assaying the enzyme activity in accordance with an opptionally modified version of the method of Lorand et al. (Lorand, L. et al. (1971) Anal Biochem. 44 (1):221-231).
An enzyme reaction solution (0.1 ml) (100 mM HEPES-NaOH, pH 7.5, 1 mM CaCl2, 20 μM monodansyl cadaverine, 0.05 mg/ml N,N-dimethylcasein, 5 μg/ml TGase) was introduced into wells of a 96-well plate (Nunc, 96 Well Black Plate with Clear Bottom). A test compound was added in concentrations of 0.3, 1.0, 3.0, 10, and 30 μM. The solution and the compound were sufficiently mixed while preventing foaming. The plate was set in the fluorescence drug screening system FDSS 3000 (Hamamatsu Photonics K.K.). TGase-inhibiting activity of the compound was calculated by assaying changes in fluorescence wavelength (at 340 nm) per unit time. The assay level at which a fluorescence change was observed with the addition of DMSO (dimethyl sulfoxide) (1 μl) used as a control instead of the test compound was designated as 100. The assay level at which TGase activity decreased by half in the presence of the test compound was designated as TG 50.
Hereafter, the numerals in parentheses written after the TG level, the SOCE level, and the IICR level correspond to the test compound concentrations. The number following the name of each title compound used in the Examples below represents a compound ID number designated arbitrarily by the present inventors.
Benzene (1 mL), acryloyl chloride (0.4 mL), and aluminium chloride (0.33 g) were added to dichloromethane (4 mL), followed by stirring at 0° C. for 2 hours. After reaction, 1 N hydrochloric acid and dichlormethane (5 mL) were added in order. The organic phase was concentrated. The obtained residue was applied to a silica gel column to obtain the title compound (120 mg).
NMR (CDCl3) 5.85 (d, 1H), 6.45 (d, 1H), 7.2-8.9 (m, 6H)
TG 46 (1 μmol) 16.8 (3 μmol) 4.8 (10 μmol) 5.9 (30 μmol)
Toluene (0.3 mL), acryloyl chloride (0.23 g), and aluminium chloride (0.33 g) were treated in the same manner as described in Example 1 to obtain the title compound (90 mg).
NMR (CDCl3) 2.85 (s, 3H), 5.85 (d, 1H), 6.45 (d, 1H), 7.0-7.9 (m, 5H)
TG 72.8 (1 μmol) 39.9 (3 μmol) 18 (10 μmol) 5.0 (30 μmol)
Fluorobenzene (0.5 mL), acryloyl chloride (0.23 g), and aluminium chloride (0.33 g) were treated in the same manner as described in Example 1 to obtain the title compound (90 mg).
NMR (CDCl3) 6.05 (m, 1H), 6.45 (d, 1H), 7.0-8.0 (m, 5H)
TG 72.8 (1 μmol) 39.9 (3 μmol) 18 (10 μmol) 5.0 (30 μmol)
1-bromonaphthalene (0.42 g), acryloyl chloride (0.31 g), and aluminium chloride (0.27 g) were treated in the same manner as described in Example 1 to obtain the title compound (22 mg).
NMR (CDCl3) 5.95 (m, 1H), 6.52 (d, 1H), 7.35-8.20 (m, 5H)
TG 90.5 (1 μmol) 78.17 (3 μmol) 60.7 (10 μmol) 24.4 (30 μmol)
Naphthalene (0.128 g), acryloyl chloride (0.11 g), and aluminium chloride (0.15 g) were treated in the same manner as described in Example 1 to obtain the title compound (75 mg).
NMR (CDCl3) 6.00 (m, 1H), 6.5 (d, 1H), 7.35-8.00 (m, 8H)
TG 44.1 (3 μmol) 11.3 (10 μmol) 0.4 (30 μmol)
Anthracene (0.156 g), acryloyl chloride (0.11 g), and aluminium chloride (0.15 g) were treated in the same manner as described in Example 1 to obtain the title compound (56 mg).
NMR (CDCl3) 5.95 (m, 1H), 6.45 (d, 1H), 7.00-7.80 (m, 10H)
TG 90.3 (3 μmol) 78.7 (10 μmol) 68.0 (30 μmol)
TG 81.3 (1 μmol) 79.0 (3 μmol)
2-chloroethylpropionyl chloride (2.78 g), naphthalene (2.56 g), and aluminium chloride (3.2 g) were reacted in nitrobenzene (9 mL) at 0° C., followed by treatment with hydrochloric acid to obtain the title compound (1.5 g).
NMR (CDCl3) 3.60 (m, 2H), 3.95 (m, 2H), 6.70-8.20 (m, 7H)
TG 59.1 (3 μmol) 39.2 (10 μmol) 0.1 (30 μmol)
2-chloroethylpropionyl chloride (0.63 g), anthracene (0.89 g), and aluminium chloride (0.8 g) were reacted in nitrobenzene (2.3 mL) at 0° C., followed by treatment with hydrochloric acid to obtain the title compound (1.5 g).
NMR (CDCl3) 3.50 (m, 2H), 4.4 (m, 2H), 7.20-8.10 (m, 9H)
TG 59.1 (3 μmol) 39.2 (10 μmol) 0.1 (30 μmol)
TG 100 (3 μmol) 100 (10 μmol) 96.9 (30 μmol)
2-chloroethylpropionyl chloride (0.63 g), fluorobenzene (0.48 g), and aluminium chloride (0.8 g) were reacted in nitrobenzene (2.3 mL) at 0° C., followed by treatment with hydrochloric acid to obtain the title compound (0.2 g).
NMR (CDCl3) 3.5 (m, 2H), 4.3 (m, 2H), 7.2-8.1 (m, 4H)
TG 49.6 (3 μmol) 22.4 (10 μmol) 5.6 (30 μmol)
2-chloroethylpropionyl chloride (0.63 g), toluene (0.885 g), and aluminium chloride (0.8 g) were reacted in nitrobenzene (1 mL) at 0° C., followed by treatment with hydrochloric acid to obtain the title compound (0.25 g).
NMR (CDCl3) 2.1 (s, 3H) 3.5 (m, 2H), 4.1 (m, 2H), 6.8-8.2 (m, 4H)
TG 89.5 (3 μmol) 50.7 (10 μmol) 3.7 (30 μmol)
2-chloroethylpropionyl chloride (0.63 g), bromobenzene (0.46 g), and aluminium chloride (0.8 g) were reacted in nitrobenzene (1 mL) at 0° C., followed by treatment with hydrochloric acid to obtain the title compound (0.25 g).
NMR (CDCl3) 3.55 (m, 2H), 4.15 (m, 2H), 6.82-8.24 (m, 4H)
TG 90.2 (3 μmol) 52.5 (10 μmol) 7.8 (30 μmol)
Benzene (1 mL), methacryloyl chloride (0.156 mg), and aluminium chloride (199 mg) were reacted in carbon disulfide (2 mL) at from 0° C. to room temperature for 2 hours. The resultant was treated in the same manner as described in Example 1 to obtain the title compound (106 mg).
NMR (CDCl3) 2.16 (m, 3H), 5.62 (m, 1H), 6.20 (d, 1H), 7.2-7.7 (m, 5H)
TG 95.2 (3 μmol) 98.4 (10 μmol) 88.7 (30 μmol)
Naphthalene (128 mg), methacryloyl chloride (0.156 mg), and aluminium chloride (199 mg) were reacted in carbon disulfide (2 mL) at from 0° C. to room temperature for 2 hours. The resultant was treated in the same manner as described in Example 1 to obtain the title compound (65 mg).
NMR (CDCl3) 1.95 (m, 3H), 5.65 (m, 1H), 6.20 (d, 1H)), 7.3-8.0 (m, 7H)
TG 88.3 (3 mol 93.0 (10 μmol) 86.7 (30 μmol)
Benzene (1 mL), cinnamoyl chloride (0.160 mg), and aluminium chloride (150 mg) were reacted in carbon disulfide (5 mL) at from 0° C. to room temperature for 2 hours. The resultant was treated in the same manner as described in Example 1 to obtain the title compound (35 mg).
NMR (CDCl3) 6.45 (d, 1H), 6.60 (d, 1H), 7.4-8.0 (m, 10H)
TG 95.4 (3 μmol) 95.4 (10 μmol) 90.7 (30 μmol)
Naphthalene (128 mg), cinnamoyl chloride (0.160 mg), and aluminium chloride (150 mg) were reacted in carbon disulfide (5 mL) at from 0° C. to room temperature. The resultant was treated in the same manner as described in Example 1 to obtain the title compound (35 mg).
NMR (CDCl3) 6.65 (s, 1H), 6.68 (a1H) 7.4-8.0 (m, 12H)
TG 96.0 (3 μmol) 95.9 (10 μmol) 86.3 (30 μmol)
Toluene (1 mL), cinnamoyl chloride (100 mg), and aluminium chloride (150 mg) were reacted in carbon disulfide (5 mL) at from 0° C. to room temperature for 2 hours. The resultant was treated in the same manner as described in Example 1 to obtain the title compound (35 mg).
NMR (CDCl3) 2.05 (s, 3H), 5.50 (s, 1H), 5.84 (s, 1H), 7.20-7.95 (m, 4H)
TG 100 (3 μmol) 98.5 (10 μmol) 86.7 (30 μmol)
Fluorobenzene (1 mL), cinnamoyl chloride (100 mg), and aluminium chloride (150 mg) were reacted in carbon disulfide (5 mL) at from 0° C. to room temperature for 2 hours. The resultant was treated in the same manner as described in Example 1 to obtain the title compound (52 mg).
NMR (CDCl3) 6.65 (s, 1H), 6.68 (a1H), 7.4-8.0 (m, 12H)
TG 99.1 (3 μmol) 100 (10 μmol) 100 (30 μmol)
Bromobenzene (0.5 mL), acryloyl chloride (110 mg), and aluminium chloride (160 mg) were reacted in dichloromethane (1.5 mL) at from 0° C. to room temperature for 4 hours. The resultant was treated in the same manner as described in Example 1 to obtain the title compound (1207.0 mg).
NMR (CDCl3) 7.00-7.95 (m, 7H)
TG 32.2 (3 μmol) 31.0 (10 μmol) 6.6 (30 μmol)
Bromobenzene (0.5 mL), acryloyl chloride (110 mg), and aluminium chloride (160 mg) were reacted in dichloromethane (1.5 mL) at from 0° C. to room temperature for 4 hours. The resultant was treated in the same manner as described in Example 1 to obtain the title compound (1207 mg).
NMR (CDCl3) 7.00-7.95 (m, 7H)
TG 32.2 (3 μmol) 31.0 (10 μmol) 6.6 (30 μmol)
NMR (CDCl3) 3.7 (s, 3H), 5.8 (m, 1H), 6.3 (m, 1H), 6.8-7.5 (m, 4H)
TG 81.2 (3 μmol) 73.6 (10 μmol) 57.0 (30 μmol)
Bromobenzene (0.5 mL), methacryloyl chloride (110 mg), and aluminium chloride (150 mg) were reacted in dichloromethane (1.5 mL) at from −20° C. to room temperature for 4 hours. The resultant was treated in the same manner as described in Example 1 to obtain the title compound (1207 mg).
NMR (CDCl3) 2.0 (m, 3H), 5.57 (s, 1H), 6.25 (m, 1H), 7.2-7.5 (m, 5H)
TG 90.0 (3 μmol) 99 (10 μmol) 100 (30 μmol)
3-methoxybromobenzene (238 mg), methacryloyl chloride (110 mg), and aluminium chloride (160 mg) were reacted in dichloromethane (1.5 mL) at from 0° C. to room temperature for 4 hours. The resultant was treated in the same manner as described in Example 1 to obtain the title compound (120 mg).
NMR (CDCl3) 3.8 (m, 3H), 5.62 (m, 1H), 5.93 (m, 1H), 6.8-7.4 (m, 3H)
TG 86 (3 μmol) 97 (10 μmol) 100 (30 μmol)
3,4-dimethoxymethylene bromobenzene (201 mg), methacryloyl chloride (110 mg), and aluminium chloride (160 mg) were reacted in dichloromethane (1.5 mL) at from 0° C. to room temperature for 4 hours. The resultant was treated in the same manner as described in Example 1 to obtain the title compound (110 mg).
NMR (CDCl3) 2.15 (m, 3H), 5.62 (m, 1H), 5.8 (m, 2H), 5.9 (m, 1H), 6.2 (m, 1H), 6.7-7.4 (m, 2H)
TG 94 (3 μmol) 90 (10 μmol) 93 (30 μmol)
Paraxylene (1 mL), methacryloyl chloride (110 mg), and aluminium chloride (160 mg) were reacted in dichloromethane (1.5 mL) at from 0° C. to room temperature for 4 hours. The resultant was treated in the same manner as described in Example 1 to obtain the title compound (140 mg).
NMR (CDCl3) 2.3-2.4 (m, 6H), 5.77 (m; 1H), 5.95 (m, 1H), 6.9-7.2 (m, 3H)
TG 86 (3 μmol 96 (10 μmol 87 (30 μmol)
Paraxylene (0.5 mL), methacryloyl chloride (110 mg), and aluminium chloride (150 mg) were reacted in dichloromethane (1.5 mL) at from 0° C. to room temperature for 4 hours. The resultant was treated in the same manner as described in Example 1 to obtain the title compound (89 mg).
NMR (CDCl3) 2.3-2.6 (m, 6H), 6.8-7.4 (m, 5H)
TG 100 (3 μmol) 66 (10 μmol) 12.9 (30 μmol)
1-methylnaphthalene (142 mg), methacryloyl chloride (110 mg), and aluminium chloride (160 mg) were reacted in dichloromethane (1.5 mL) at from −30° C. to room temperature for 4 hours. The resultant was treated in the same manner as described in Example 1 to obtain the title compound (122 mg).
NMR (CDCl3) 2.8-2.9 (m, 6H), 5.3 (m, 1H), 6.9 (m, 1H), 7.2-8.0 (m, 6H)
TG 100 (3 μmol) 100 (10 μmol) 88 (30 μmol)
1-methylnaphthalene (142 mg), acryloyl chloride (100 mg), and aluminium chloride (150 mg) were reacted in carbon disulfide (0.5 mL) at from −20° C. to room temperature for 1 hour. The resultant was treated in the same manner as described in Example 1 to obtain the title compound (169 mg) in a viscous liquid form.
NMR (CDCl3) 6.0 (m, 1H), 6.27 (m, 1H), 6.95 (m, 1H), 7.2-8.0 (m, 6H)
TG 85.1 (0.3 μmol) 64.1 (1 μmol) 22.2 (3 μmol) 9.8 (10 μmol) 4.9 (30 μmol)
4-acetylpyridine (121 mg), t-butyl-2-hydroxyethyl amine (117 mg), and paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 130° C. for 2 hours.
NMR (CDCl3) 1.05 (s, 9H), 2.6-2.8 (m, 4H), 3.6 (m, 2H), 8.81 (s, 2H)
TG 75.9 (3 μmol) 12.8 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 20 (10 μmol) 10 (30 μmol) 10 (100 μmol)
4-acetylpyridine (121 mg), methylbenzylamine (121 mg), and paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 130° C. for 2 hours.
NMR (CDCl3) 2.1 (s, 3H), 2.6 (m, 2H), 2.8 (m, 2H), 3.4 (m, 2H)
TG 27.4 (3 μmol) 0.5 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 40 (10 μmol) 60 (30 μmol) 80 (100 μmol)
Benzene (1 mL), tigloyl chloride (236 mg), and aluminium chloride (160 mg) were reacted in dichloromethane (1.5 mL) at from 0° C. to room temperature for 4 hours. The resultant was treated in the same manner as described in Example 1 to obtain the title compound (126 mg).
NMR (CDCl3) 1.9-2.0 (m, 6H), 5.9 (m, 1H), 6.8-7.0 (m, 5H)
TG 100 (3 μmol) 100 (10 μmol) 100 (30 μmol)
Benzene (1 mL), crotonoyl chloride (236 mg), and aluminium chloride (280 mg) were reacted in dichloromethane (1.5 mL) at from −30° C. to room temperature for 16 hours. The resultant was treated in the same manner as described in Example 1 to obtain the title compound (66 mg).
NMR (CDCl3) 1.9-2.0 (m, 3H), 5.8 (m, 2H), 6.9-7.0 (m, 5H)
TG 100 (3 μmol) 100 (10 μmol) 100 (30 μmol)
Naphthalene (128 mg), crotonoyl chloride (124 mg), and aluminium chloride (180 mg) were reacted in dichloromethane (1.5 mL) at from −20° C. to room temperature for 4 hours. The resultant was treated in the same manner as described in Example 1 to obtain the title compound (126 mg).
NMR (CDCl3) 2.0 (m, 3H), 5.9 (m, 1H), 6.6 (m, 1H), 6.8-8.2 (m, 7H)
TG 100 (3 μmol) 100 (10 μmol) 88 (30 μmol)
Benzene (1 mL), crotonoyl chloride (236 mg), and aluminium chloride (160 mg) were reacted in dichloromethane (1.5 mL) at from 0° C. to room temperature for 4 hours. The resultant was treated in the same manner as described in Example 1 to obtain the title compound (126 mg).
NMR (CDCl3) 1.9-2.0 (m, 6H), 5.9 (m, 1H), 6.8-7.0 (m, 5H)
TG 90 (3 μmol) 85 (10 μmol) 57 (30 μmol)
Anisole (0.3 mL), crotonoyl chloride (24 mg), and aluminium chloride (160 mg) were reacted in dichloromethane (1.5 mL) at from −50° C. to room temperature for 4 hours. The resultant was treated in the same manner as described in Example 1 to obtain the title compound (75 mg).
NMR (CDCl3) 1.95 (m, 3H), 3.9 (m, 3H), 6.96 (m, 2H), 7.06 (m, 1H), 7.25 (m, 1H), 7.95 (m, 2H)
TG 96 (3 μmol) 74 (10 μmol 67 (30 μmol)
2-methoxynaphthalene (158 mg), crotonoyl chloride (124 mg), and aluminium chloride (150 mg) were reacted in dichloromethane (1.5 mL) at from 0° C. to room temperature for 4 hours. The resultant was treated in the same manner as described in Example 1 to obtain the title compound (156 mg).
NMR (CDCl3) 1.9-2.0 (m, 3H), 3.9 (m, 3H), 5.9 (m, 1H), 5.6 (m, 1H), 7.2-7.9 (m, 6H)
TG 100 (3 μmol) 100 (10 μmol 100 (30 μmol)
Anisole (108 mg), acryloyl chloride (154 mg), and aluminium chloride (199 mg) were reacted in dichloromethane (1.5 mL) at from −20° C. to room temperature for 4 hours. The resultant was treated in the same manner as described in Example 1 to obtain the title compound (160 mg).
NMR (CDCl3) 3.95 (m, 3H), 6.48-8.00 (m, 7H)
TG 100 (3 μmol) 100 (10 μmol) 93 (30 μmol)
Anisole (128 mg), tigloyl chloride (140 mg), and aluminium chloride (155 mg) were reacted in dichloromethane (1.5 mL) at from 0° C. to room temperature for 4 hours. The resultant was treated in the same manner as described in Example 1 to obtain the title compound (63 mg).
NMR (CDCl3) 1.9 (d, 3H), 2.9 (d, 3H) 3.8 (m, 3H), 5.13 (m, 1H), 6.9-76 (m, 4H)
TG 63 (3 μmol) 26 (10 μmol 8.2 (30 μmol)
Benzene (0.5 mg), 4-chlorobutyryl chloride (141 mg), and aluminium chloride (170 mg) were reacted in dichloromethane (1.5 mL) at from 0° C. to room temperature for 4 hours. The resultant was treated in the same manner as described in Example 1 to obtain the title compound (10.3 mg).
NMR (CDCl3) 2.30 (m, 2H), 3.20 (m, 2H), 3.93 (m, 2H), 7.45-8.10 (m, 5H)
TG 85 (3 μmol) 92 (10 μmol) 83 (30 μmol)
Ethylbenzene (0.5 mL), acryloyl chloride (120 mg), and aluminium chloride (199 mg) were reacted in dichloromethane (1.5 mL) at from 0° C. to room temperature for 4 hours. The resultant was treated in the same manner as described in Example 1 to obtain the title compound (110 mg).
NMR (CDCl3) 1.2 (m, 3H), 2.62 (m, 2H), 5.93 (m, 1H), 6.4 (m, 1H), 7.0-7.9 (m, 5H)
TG 71 (3 μmol) 55 (10 μmol) 21 (30 μmol)
Metaxylene (128 mg), acryloyl chloride (154 mg), and aluminium chloride (160 mg) were reacted in dichloromethane (1.5 mL) at from 0° C. to room temperature for 4 hours. The resultant was treated in the same manner as described in Example 1 to obtain the title compound (31 mg).
NMR (CDCl3) 2.42 (m, 6H), 7.0-7.8 (m, 4H)
TG 88 (3 μmol) 93 (10 μmol) 85 (30 μmol)
Benzene (0.5 mL), chloroacetyl chloride (120 mg), and aluminium chloride (180 mg) were reacted in dichloromethane (1.5 mL) at from −40° C. to room temperature for 2 hours. The resultant was treated in the same manner as described in Example 1 to obtain the title compound (11 mg).
NMR (CDCl3) 4.7 (s, 2H), 7.45 (m, 2H), 7.2 (m, 1H), 7.86 (m, 2H)
TG 59 (3 μmol) 28 (10 μmol) 12 (30 μmol)
Orthoxylene (0.5 mL), acryloyl chloride (120 mg), and aluminium chloride (150 mg) were reacted in dichloromethane (1.5 mL) at from 0° C. to room temperature for 4 hours. The resultant was treated in the same manner as described in Example 1 to obtain the title compound (160 mg).
NMR (CDCl3) 2.20-2.25 (m, 6H), 5.58 (d, 1H), 6.42 (d, 1H), 7.0-7.5 (m, 4H)
TG 51 (3 μmol) 30 (10 μmol) 10 (30 μmol)
5-t-butylmetaxylene (0.5 mL), acryloyl chloride (120 mg), and aluminium chloride (150 mg) were reacted in dichloromethane (1.5 mL) at from −40° C. to room temperature for 2 hours. The resultant was treated in the same manner as described in Example 1 to obtain the title compound (120 mg).
NMR (CDCl3) 1.2 (s, 9H), 2.22 (m, 6H), 6.5-6.6 (m, 2H)
TG 86 (3 μmol) 97 (10 μmol) 99 (30 μmol)
1,2-dimethoxybenzene (135 mg), acryloyl chloride (118 mg), and aluminium chloride (199 mg) were reacted in dichloromethane (1.5 mL) at from −40° C. to room temperature for 2 hours. The resultant was treated in the same manner as described in Example 1 to obtain the title compound (55 mg).
NMR (CDCl3) 3.8 (m, 6H), 6.4 (m, 1H), 5.75 (m, 1H), 6.7-7.5 (m, 4H)
TG 87 (3 μmol) 79 (10 μmol) 47 (30 μmol)
Diphenyl (154 mg), acryloyl chloride (220 mg), and aluminium chloride (319 mg) were reacted in dichloromethane (5 mL) at from 0° C. to room temperature for 4 hours. The resultant was treated in the same manner as described in Example 1 to obtain the title compound (240 mg).
NMR (CDCl3) 5.95 (m, 1H), 6.48 (m, 1H), 7.3-8.0 (m, 7H)
TG 88 (3 μmol) 52 (10 μmol 15 (30 μmol)
Diphenylether (170 mg), acryloyl chloride (220 mg), and aluminium chloride (319 mg) were reacted in dichloromethane (6 mL) at from 0° C. to room temperature for 4 hours. The resultant was treated in the same manner as described in Example 1 to obtain the title compound (390 mg).
NMR (CDCl3) 5.91 (m, 1H), 6.5 (m, 1H), 6.9-8.2 (m, 10H)
TG 88 (3 μmol) 52 (10 μmol) 15 (30 μmol)
Diphenylether (170 mg), acryloyl chloride (220 mg), and aluminium chloride (319 mg) were reacted in dichloromethane (6 mL) at from 0° C. to room temperature for 4 hours. The resultant was treated in the same manner as described in Example 1 to obtain the title compound (390 mg).
NMR (CDCl3) 5.91 (m, 1H), 6.5 (m, 1H), 6.9-8.2 (m, 10H)
TG 88 (3 μmol) 52 (10 μmol) 15 (30 μmol)
1-fluoronaphthalene (146 mg), acryloyl chloride (110 mg), and aluminium chloride (150 mg) were reacted in dichloromethane (1 mL) at from −15° C. to room temperature for 2 hours. The resultant was treated in the same manner as described in Example 1 to obtain the title compound (390 mg).
NMR (CDCl3) 5.80 (m, 1H), 6.3 (m, 1H), 6.5 (m, 1H), 6.9-8.8 (m, 7H)
TG 46 (3 μmol) 18 (10 μmol) 7 (30 μmol)
4-acetylpyridine (124 mg), 2-hydroxyethylbutyl amine (117 mg), and paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 130° C. for 2 hours.
NMR (CDCl3) 0.8 (s, 3H), 1.1-1.5 (m, 4H), 2.42 (m, 2H), 2.6 (m, 2H), 2.9 (m, 2H), 3.8 (m, 2H), 3.5 (m, 2H), 4.4 (m, 2H), 7.8 (m, 2H), 8.8 (m, 2H)
TG 42.7 (3 μmol) 3.4 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 0 (10 μmol) 20 (30 μmol) 100 (100 μmol)
Diphenylether (170 mg), acryloyl chloride (220 mg), and aluminium chloride (319 mg) were reacted in dichloromethane (6 mL) at from 0° C. to room temperature for 4 hours. The resultant was treated in the same manner as described in Example 1 to obtain the title compound (390 mg).
NMR (CDCl3) 5.9 (m, 1H), 6.5 (m, 1H), 7.0-8.1 (m, 14H)
TG 102 (3 μmol) 92 (10 μmol) 61 (30 μmol)
Phenyl sulfide (188 mg), acryloyl chloride (300 mg), and aluminium chloride (440 mg) were reacted in dichloromethane (2 mL) at from −40° C. to room temperature for 2 hours. The resultant was treated in the same manner as described in Example 1 to obtain the title compound (390 mg).
NMR (CDCl3) 5.9 (m, 1H), 6.5 (m, 1H), 7.29-7.90 (m, 10H)
TG 97 (3 μmol) 88 (10 μmol) 34 (30 μmol)
Chlorobenzene (0.3 mL), acryloyl chloride (120 mg), and aluminium chloride (115 mg) were reacted in dichloromethane (1 mL) at from 0° C. to room temperature for 4 hours. The resultant was treated in the same manner as described in Example 1 to obtain the title compound (390 mg).
NMR (CDCl3) 5.91 (m, 1H), 6.4 (m, 1H), 7.2-7.9 (m, 5H)
TG 27 (3 μmol) 10 (10 μmol) 7.9 (30 μmol)
Pyridine (0.5 mL), acryloyl chloride (120 mg), and aluminium chloride (150 mg) were reacted in dichloromethane (1 mL) at from 0° C. to room temperature for 2 hours. The resultant was treated in the same manner as described in Example 1 to obtain the title compound (37.9 mg).
NMR (CDCl3) 5.9 (m, 1H), 6.6 (m, 1H), 6.0-8.2 (m, 5H)
TG 78 (3 μmol) 75 (10 μmol) 52 (30 μmol)
3-acetylthiophene (121 mg), isopropyl-2-hydroxyethyl amine (126 mg), and paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 130° C. for 2 hours.
NMR (CDCl3) 1.05 (m, 6H), 2.4 (m, 4H), 2.9 (m, 2H), 3.8 (m, 2H), 4.3 (m, 2H), 7.3 (s, 1H), 7.9 (s, 1H), 8.0 (s, 1H)
TG 70.9 (3 μmol) 0.2 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 50 (100 μmol)
TG 84 (3 μmol) 94 (10 μmol) 37 (30 μmol)
1-chloronaphthalene (183 mg), acryloyl chloride (120 mg), and aluminium chloride (150 mg) were reacted in dichloromethane (1.5 mL) at from −40° C. to room temperature for 2 hours. The resultant was treated in the same manner as described in Example 1 to obtain the title compound (277 mg).
NMR (CDCl3) 6.0 (d, 1H), 6.9 (m, 1H), 7.3-8.5 (m, 6H)
TG 15.1 (3 μmol) 4.8 (10 μmol) 2.6 (30 μmol)
Diphenylmethane (168 mg), acryloyl chloride (200 mg), and aluminium chloride (280 mg) were reacted in dichloromethane (2 mL) at from −40° C. to room temperature for 2 hours. The resultant was treated in the same manner as described in Example 1 to obtain the title compound (190 mg).
NMR (CDCl3) 6.0 (m, 1H), 6.5 (m, 1H), 6.4 (m, 1H), 7.5-8.2 (m, 8H)
TG 6.7, 14.1 (3 μmol) 1.7, 4.8 (10 μmol) 0.6, 3.0 (30 μmol)
1-phenylnaphthalene (204 mg), acryloyl chloride (200 mg), and aluminium chloride (290 mg) were reacted in dichloromethane (1.5 mL) at from −40° C. to room temperature for 2 hours. The resultant was treated in the same manner as described in Example 1 to obtain the title compound (323 mg).
NMR (CDCl3) 5.95 (d, 1H), 6.1 (d, 1H), 6.5-8.0 (m, 11H)
TG 70.6 (3 μmol) 41.1 (10 μmol) 19.1 (30 μmol)
Benzaldehyde (342 mg) was mixed with THF (4 ml) and further mixed with vinylmagnesium bromide (1 N solution) (4 mL), followed by stirring for 12 hours to obtain the title compound (320 mg).
NMR (CDCl3) 5.42 (d, 1H), 5.23 (m, 1H), 6.1 (m, 1H), 7.3-7.4 (m, 5H)
TG 100 (3 μmol) 100 (10 μmol) 62 (30 μmol)
p-anisaldehyde (136 mg) was mixed with THF (4 ml) and further mixed with vinylmagnesium bromide (1 N solution) (4 mL), followed by stirring for 12 hours to obtain the title compound (195 mg).
NMR (CDCl3) 3.80 (s, 3H), 5.2 (m, 1H), 6.1 (d, 1H), 6.2 (s, 1H), 6.95 (m, 2H), 7.3 (m, 2H)
TG100 (3 μmol) 100 (10 μmol) 82 (30 μmol)
2-naphthylaldehyde (300 mg) was mixed with THF (4 ml) and further mixed with vinylmagnesium bromide (1 N solution) (4 mL), followed by stirring for 12 hours to obtain the title compound (352 mg).
NMR (CDCl3) 5.25 (m, 1H), 5.39 (m, 1H), 6.14 (d, 1H), 7.5 (m, 3H), 7.85 (m, 4H)
TG 100 (3 μmol) 89 (10 μmol) 71.5 (30 μmol)
Acryloyldiphenylmethane (22 mg), isopropylbenzylamine (14.9 mg), and diisopropylethyl amine (5 mg) were reacted in dichlormethane (0.2 ml) at 50° C. for 2 hours.
NMR (CDCl3) 1.05 (m, 6H), 2.5 (m, 2H), 3.0 (m, 2H), 3.5 (m, 2H), 3.6 (m, 2H), 7.5 (m, 3H), 7.85 (m, 4H).
TG 45.8 (3 mol) 17.5 (10 μmol) 8.7 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 30 (100 μmol)
IICR 50 (10 μmol) 70 (30 μmol) 96 (100 μmol)
Acryloyl toluene (15 mg), isopropylbenzylamine (14.9 mg), and diisopropylethyl amine (5 mg) were reacted in dichlormethane (0.2 ml) at 50° C. for 2 hours.
NMR (CDCl3) 1.05 (m, 6H), 2.5 (m, 4H), 3.0 (m, 2H), 3.0 (m, 1H), 3.7 (m, 2H), 6.8-7.8 (m, 9H)
TG 88.8 (3 μmol) 62 (10 μmol) 16.3 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 30 (100 μmol)
IICR 30 (10 μmol) 10 (30 μmol) 30 (100 μmol)
2-acetonaphthone (17 mg), isopropylbenzylamine (149 mg), and paraformaldehyde (39 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 1.05 (m, 6H), 2.5 (m, 2H), 3.0 (m, 2H), 3.0 (m, 1H), 3.7 (m, 2H), 7.1-7.9. (m, 12H)
TG 80.2 (3 μmol) 62.4 (10 μmol) 17.5 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 10 (10 μmol) 10 (30 μmol) 70 (100 μmol)
Vinyl-4-methoxy phenylcarbinol (172 mg) was oxidized with pyridinium chlorochromate (230 mg).
NMR (CDCl3) 2.9 (m, 3H), 5.7 (m, 1H), 6.3 (m, 1H), 7.2 (m, 1H), 7.7 (m, 4H)
TG 83.9 (3 μmol) 53.6 (10 μmol) 16.8 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 40 (10 μmol) 40 (30 μmol) 70 (100 μmol)
Vinyl-1-naphthylcarbinol (184 mg) was oxidized with pyridinium chlorochromate (214 mg).
NMR (CDCl3) 5.25 (m, 1H), 6.05 (m, 1H), 6.14 (d, 1H), 7.2-8.3 (m, 7H)
TG 33.1 (3 μmol) 7.8 (10 μmol) 0.8 (30 μmol)
SOCE 0 (10 μmol) 10 (30 μmol 70 (100 μmol)
IICR 80 (10 μmol) 90 (30 μmol) 95 (100 μmol)
Acetophenone (17 mg), isopropylbenzylamine (149 mg), and paraformaldehyde (39 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours reaction.
NMR (CDCl3) 1.05 (m, 6H), 2.5 (m, 2H), 3.0 (m, 2H), 3.0 (m, 1H), 3.7 (m, 2H), 6.5 (1H), 7.0-7.9 (m, 10H)
TG 68.4 (3 μmol) 40.2 (10 μmol) 3.4 (30 μmol)
SOCE 0 (10 μmol) 10 (30 μmol) 20 (100 μmol)
IICR 20 (10 μmol) 20 (30 μmol) 90 (100 μmol)
1-acetonaphthone (170 mg), diphenyl amine (169 mg), and paraformaldehyde (39 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 2.8 (m, 2H), 3.2 (m, 2H), 7.0-8.05 (m, 17H)
TG 100 (3 μmol) 91 (10 μmol) 74 (30 μmol)
SOCE 0 (10 μmol) 10 (30 μmol 20 (100 μmol)
IICR 10 (10 μmol) 0 (30 μmol) 40 (100 μmol
2-acetonaphthone (170 mg), methylbenzylamine (121 mg), and paraformaldehyde (39 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 2.3 (m, 2H), 2.8 (m, 2H), 3.8 (m, 5H), 7.4-80 (m, 12H)
TG 92.9 (3 μmol) 82.7 (10 μmol) 31.8 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
4-methoxyacetophenone (150 mg), isopropylbenzylamine (149 mg), and paraformaldehyde (39 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 1.05 (m, 6H), 2.5 (m, 2H), 3.0 (m, 2H), 3.0 (m, 1H), 3.7 (m, 2H), 3.9 (s, 3H), 6.9-8.0 (m, 9H)
TG 93.6 (3 μmol) 87.5 (10 μmol) 43.1 (30 μmol)
SOCE 0 (10 μmol) 10 (30 μmol) 20 (100 μmol)
IICR 20 (10 μmol) 20 (30 μmol) 70 (100 μmol)
2-acetylpyridine (121 mg), isopropylbenzylamine (149 mg), and paraformaldehyde (39 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 1.05 (m, 6H), 2.5 (m, 2H), 3.0 (m, 2H), 3.0 (m, 1H), 3.7 (m, 2H), 7.0-8.1 (m, 9H)
TG 84 (0.3 mol) 52 (1 μmol) 16.9 (3 μmol) 9.5 (10 μmol) 4.4 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 10 (100 μmol)
IICR 70 (10 μmol) 100 (30 μmol) 90 (100 μmol)
1-acetonaphthone (170 mg), methylbenzylamine (121 mg), and paraformaldehyde (39 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 2.2 (m, 3H), 2.7 (m, 2H), 3.0 (m, 2H), 3.7 (m, 2H), 7.3-8.0 (m, 12H)
TG 96.1 (3 μmol) 89 (10 μmol) 65 (30 μmol)
SOCE 0 (10 μmol) 10 (30 μmol) 30 (100 μmol)
IICR 30 (10 μmol) 50 (30 μmol) 70 (100 μmol)
2-acetonaphthone (170 mg), dibenzyl amine (169 mg), and paraformaldehyde (39 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 2.5 (m, 2H), 3.7 (m, 2H), 6.7-8.0 (m, 17H)
TG 91.4 (3 μmol) 66.1 (10 μmol) 35.1 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
1-4-methoxyacetophenone (150 mg), methylbenzylamine (121 mg), and paraformaldehyde (39 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 2.2 (m, 3H), 2.5 (m, 2H), 3.7 (m, 2H), 3.9 (m, 5H), 6.9-8.0 (9H)
TG 93.5 (3 μmol) 82 (10 μmol) 57 (30 μmol)
SOCE 0 (10 μmol 10 (30 μmol) 20 (100 μmol)
IICR 0 (10 μmol) 10 (30 μmol) 30 (100 μmol)
2-acetylpyridine (150 mg), methylbenzylamine (121 mg), and paraformaldehyde (39 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours reaction.
NMR (CDCl3) 2.27 (s, 3H), 2.5 (m, 2H), 3.0 (m, 2H), 3.7 (m, 2H), −8.0 (9H)
TG 85.2 (3 μmol) 71.2 (10 μmol) 23.4 (30 μmol)
SOCE 0 (10 μmol 20 (30 μmol) 30 (100 μmol)
IICR 0 (10 μmol) 10 (30 μmol) 30 (100 μmol)
5-methylacryloylnaphthalene (14.8 mg) and methylbenzylamine (9.1 mg) were reacted at 50° C. for 5 hours.
NMR (CDCl3) 2.2 (s, 3H), 2.5 (m, 2H), 3.0 (m, 2H), 3.7 (m, 2H), 3.9 (s, 3H), 7.2-8.1 (m, 11H)
TG 87.9 (3 μmol) 62.7 (10 μmol) 8.2 (30 μmol)
SOCE 10 (10 μmol) 20 (30 μmol) 50 (100 μmol)
IICR 20 (10 μmol) 70 (30 μmol) 90 (100 μmol)
5-methylacryloylnaphthalene (14.8 mg) and isopropylbenzylamine (9.1 mg) were reacted at 50° C. for 5 hours.
NMR (CDCl3) 1.05 (m, 6H), 2.5 (m, 2H), 3.0 (m, 2H), 3.0 (m, 1H), 3.7 (m, 2H), 3.9 (s, 3H), 7.2-8.1 (m, 11H)
TG 64.4 (3 μmol) 28.1 (10 μmol) 1.8 (30 μmol)
SOCE 10 (10 μmol) 30 (30 μmol) 70 (100 μmol)
IICR 70 (10 μmol) 90 (30 μmol) 90 (100 μmol)
5-methylacryloylnaphthalene (14.8 mg) and diphenyl amine (9.1 mg) were reacted at 50° C. for 5 hours.
NMR (CDCl3) 2.7 (m, 2H), 3.4 (m, 2H), 4.2 (s, 3H) 6.9-8.0 (16H)
TG 72.2 (3 μmol) 54.9 (10 μmol) 10.8 (30 μmol)
SOCE 10 (10 μmol) 30 (30 μmol) 50 (100 μmol)
IICR 10 (10 μmol) 50 (30 μmol) 90 (100 μmol)
5-methylacryloylnaphthalene (21.8 mg) and piperidine (9.1 mg) were reacted at 50° C. for 5 hours.
NMR (CDCl3) 1.4-1.8 (m, 6H), 2.5 (m, 2H), 2.8 (m, 6H), 3.2 (s, 3H), 7.0-8.0 (6H)
TG 89.2 (3 μmol) 99 (10 μmol) 69.4 (30 μmol
SOCE 0 (10 μmol) 10 (30 μmol) 40 (100 μmol)
IICR 0 (10 μmol) 10 (30 μmol) 30 (100 μmol)
1-acetonaphthone (170 mg), isopropylbenzylamine (149 mg), and paraformaldehyde (39 mg) were reacted in dioxane (0.2 mol) at 140° C. for 2 hours.
NMR (CDCl3) 1.05 (m, 6H), 2.7 (m, 2H), 3.05 (m, 1H), 3.10 (m, 2H), 3.60 (m, 2H), 7.1-8.0 (m, 12H)
TG 90.3 (3 μmol) 57 (10 μmol) 6.5 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 20 (100 μmol)
IICR 50 (10 μmol) 70 (30 μmol) 100 (100 μmol)
2-(4-chlorobutanoyl)thiophene (188 mg), N-methylpiperidine (100 mg), and diisopropylethyl amine (128 mg) were heated at 100° C. for 1 hour.
NMR (CDCl3) 1.3 (m, 2H), 2.20 (m, 2H), 2.40 (m, 2H), 2.9 (m, 4H), 3.6 (m, 2H), 4.2 (s, 2H), 6.8 (s, 1H), 7.7 (s. 1H), 7.7 (s, 1H)
TG 100 (3 μmol) 100 (10 μmol) 88 (30 μmol)
Vinyl-5-chloro-2-naphthylketone (18.5 mg) and isopropylbenzylamine (12.7 mg) were reacted in dichloromethane (0.5 mL).
NMR (CDCl3) 1.05 (m, 6H), 2.5 (m, 2H), 3.0 (m, 2H), 3.0 (m, 1H), 3.7 (m, 2H), 7.0-8.9 (11H)
TG 34.5 (3 μmol) 11.6 (10 μmol) 1.4 (30 μmol)
SOCE 20 (10 μmol) 30 (30 μmol) 70 (100 μmol)
IICR 90 (10 μmol) 100 (30 μmol) 100 (100 μmol)
Vinyl-4-phenoxyphenylketone (15.9 mg) and isopropylbenzylamine (10.6 mg) were reacted in dichloromethane (0.3 mL).
NMR (CDCl3) 1.05 (m, 6H), 2.5 (m, 2H), 3.0 (m, 2H), 3.0 (m, 1H), 3.7 (m, 2H), 6.9-7.9 (14H)
TG 73.7 (3 μmol) 61.8 (10 μmol) 16.9 (30 μmol)
SOCE 10 (10 μmol) 20 (30 μmol) 30 (100 μmol)
IICR 50 (10 μmol) 50 (30 μmol) 95 (100 μmol)
Vinyl-4-phenoxyphenylketone (18.9 mg) and methylbenzylamine (10.3 mg) were reacted in dichloromethane (0.3 mL).
NMR (CDCl3) 2.5 (m, 2H), 3.0 (m, 2H), 3.7 (m, 2H), 3.9 (m, 3H), 6.9-7.9 (m, 14H)
TG 89.3 (3 μmol) 72.6 (10 μmol) 28.7 (30 μmol)
SOCE 0 (10 μmol) 20 (30 μmol) 50 (100 μmol)
IICR 30 (10 μmol) 70 (30 μmol) 95 (100 μmol)
Vinyl-4-phenoxyphenylketone (10.4 mg) and 2-amino-1-phenyl ethanol amine (10.3 mg) were reacted in dichloromethane (0.3 mL).
NMR (CDCl3) 3.2 (m, 2H), 3.4 (m, 2H), 3.7 (m, 2H), 6.8-8.0 (m, 14H)
TG 61.7 (3 μmol) 41.7 (10 μmol) 8.7 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 20 (100 μmol)
IICR 10 (10 μmol) 10 (30 μmol) 90 (100 μmol)
Vinyl-5-chloro-2-naphthylketone (21.4 mg) and piperidine (8.4 mg) were reacted in dichloromethane (0.3 mL).
NMR (CDCl3) 1.4-1.8 (m, 6H), 2.5 (m, 2H), 2.8 (m, 6H), 7.0-8.0 (6H)
TG 69.9 (3 μmol) 52.2 (10 μmol) 10.2 (30 μmol)
SOCE 0 (10 μmol) 0 (30 mol) 20 (100 μmol)
IICR 10 (10 μmol) 10 (30 μmol) 100 (100 μmol)
Vinyl-5-chloro-2-naphthylketone (14.8 mg) and benzylethanol amine (10.3 mg) were reacted in dichloromethane (0.3 mL).
NMR (CDCl3) 2.6 (m, 2H), 2.8 (m, 2H), 3.0 (m, 2H), 3.2 (m, 2H), 4.2 (m, 2H), 7.2-8.0 (11H)
TG 27.6 (3 μmol) 11.2 (10 mol) 11.2 (30 μmol)
SOCE 0 (10 μmol) 10 (30 μmol) 80 (100 μmol)
IICR 30 (10 μmol) 80 (30 μmol) 100 (100 μmol)
Vinyl-5-chloro-2-naphthylketone (28.4 mg) and 2-amino-2-ethyl-1,3-propanediol (11.4 mg) were reacted in dichloromethane (0.3 mL).
NMR (CDCl3) 0.9 (m, 3H), 1.6 (m, 2H), 3.05 (m, 2H), 3.2 (m, 2H), 3.4 (m, 2H), 3.6 (m, 2H), 7.4-8.3 (6H)
TG 64.5 (3 μmol) 44.5 (10 μmol) 11.7 (30 μmol)
SOCE 0 (10 μmol) 10 (30 μmol) 30 (100 μmol)
IICR 10 (10 μmol) 20 (30 μmol) 100 (100 μmol)
Vinyl-5-chloro-2-naphthylketone (19.1 mg) and N-n-butylethanol amine (9.9 mg) were reacted in dichloromethane (0.3 mL).
NMR (CDCl3) 0.9 (m, 3H), 1.4 (m, 4H), 2.6 (m, 2H), 3.05 (m, 2H), 3.2 (m, 2H), 3.6 (m, 2H), 3.9 (m, 2H), 7.6-8.4 (6H)
TG 31.8 (3 μmol) 14.4 (10 μmol) 18.5 (30 μmol)
SOCE 0 (10 μmol) 10 (30 μmol) 90 (100 μmol)
IICR 20 (10 μmol) 90 (30 μmol) 100 (100 μmol)
Allyl-2-naphthylcarbinol 205 mg obtained by reacting naphthylaldehyde (960 mg) and 1N allylmagnesium bromide (6.3 ml) and pyridinium chlorochromate (230 mg) were reacted in dichloromethane (2 mL) at room temperature for 4 hours.
TG 82.2 (3 μmol) 67.4 (10 μmol) 52.2 (30 μmol
SOCE 0 (10 μmol 0 (30 μmol) 0 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 30 (100 μmol)
Allyl-1-naphthylcarbinol (205 mg) and pyridinium chlorochromate (230 mg) were reacted in dichloromethane (2 mL) at room temperature for 4 hours.
TG 71 (3 μmol) 69 (10 μmol) 46 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 30 (100 μmol)
IICR 20 (10 μmol) 70 (30 μmol) 90 (100 μmol)
Acetylpyridine (121 mg), N-t-butylbenzylamine (163 mg), and paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 1.2 (m, 9H), 2.7 (m, 2H), 3.0 (m, 2H), 3.2 (m, 2H), 7.0-7.9 (m, 9H)
TG 27.3 (3 μmol) 16.0 (10 μmol) 12.2 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 30 (10 μmol) 90 (30 μmol) 100 (100 μmol)
NMR (CDCl3) 1.4 (m, 6H), 2.5 (m, 4H), 2.6 (m, 2H), 2.8 (m, 2H), 7.4-8.7 (m, 4H)
TG 89.0 (3 μmol) 76.9 (10 μmol 69.2 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 0 (10 μmol) 10 (30 μmol) 10 (100 μmol)
Acetylpyridine (121 mg), N-benzylethanol amine (151 mg), and paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 2.7 (m, 2H), 3.0 (m, 2H), 3.7 (m, 2H), 3.8 (m, 2H), 3.6 (m, 2H), 7.2-8.0 (m, 9H)
TG 56.9 (3 μmol) 41.8 (10 μmol) 15.6 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 20 (10 μmol) 30 (30 μmol) 100 (100 μmol)
Acryloylnaphthalene (11.9 mg) and acetoacetic acid methyl ester (7.6 mg) were heated with a small amount of sodium ethylate at 45° C. for 5 hours.
NMR (CDCl3) 1.6 (m, 2H), 2.6 (m, 3H), 3.6 (m, 2H), 3.8 (m, 3H), 7.4-8.3 (7H)
TG 100 (3 μmol) 77.5 (10 μmol) 47.6 (30 μmol)
SOCE 0 (10 μmol) 10 (30 μmol) 90 (100 μmol)
IICR 0 (10 μmol) 10 (30 μmol) 70 (100 μmol)
2-acryloylnaphthalene (9.9 mg) and 3-ketovaleric acid methyl ester (7.1 mg) were heated with a small amount of sodium ethylate at 45° C. for 5 hours.
NMR (CDCl3) 1.1 (m, 3H), 1.3 (m, 2H), 2.3 (m, 2H), 2.6 (m, 2H), 3.8 (m, 3H), 7.4-8.3 (7H)
TG 100 (3 μmol) 92.2 (10 μmol) 77.2 (30 μmol
SOCE 0 (10 μmol 10 (30 μmol) 60 (100 μmol)
IICR 0 (10 μmol 0 (30 μmol) 0 (100 μmol)
2-acryloylnaphthalene (17.2 mg) and N-methylbenzylamine (7.1 mg) were heated at 45° C. for 15 hours.
NMR (CDCl3) 2.5 (m, 2H), 3.0 (m, 2H), 3.7 (m, 2H), 3.9 (m, 3H), 7.2-78.0 (m, 12H)
TG 100 (3 μmol) 84 (10 μmol) 35 (30 μmol
SOCE 0 (10 μmol 0 (30 μmol) 30 (100 μmol)
IICR 0 (10 μmol) 20 (30 μmol) 60 (100 μmol)
2-acryloylnaphthalene (9.8 mg) and N-methylethanol amine (4.1 mg) were heated at 45° C. for 15 hours.
NMR (CDCl3) 2.5 (m, 2H), 2.6 (m, 2H), 3.1 (m, 2H), 3.6 (m, 2H), 3.7 (m, 3H), 6.9-7.9 (m, 7H)
TG 92.5 (3 μmol) 57.6 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol 20 (100 μmol)
IICR 0 (10 μmol 0 (30 μmol) 60 (100 μmol)
2-acetylthiophene (126 mg), ethylbenzylamine (135 mg), and paraformaldehyde (39 mg) were reacted in dioxane (0.2 ml) at 130° C. for 2 hours.
NMR (CDCl3) 1.0 (s, 3H), 2.2-3.2 (m, 6H), 3.6-3.8 (m, 2H), 7.1-8.0 (m, 8H)
TG 80.5 (3 μmol) 13.4 (30 μmol)
SOCE 10 (10 μmol) 20 (30 μmol) 40 (100 μmol)
IICR 30 (10 μmol) 70 (30 μmol) 100 (100 μmol)
1-acetylpyrazine (122 mg), diethanol amine (105 mg), and paraformaldehyde (39 mg) were reacted in dioxane (0.2 ml) at 130° C. for 2 hours.
NMR (CDCl3) 2.5-2.8 (m, 4H), 3.4-3.8 (m, 8H), 7.6 (s, 1H), 8.7 (s, 1H), 9.2 (s, 1H)
TG 57.8 (1 μmol 19.8 (3 μmol 1.1 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 0 (10 μmol) 20 (30 μmol) 100 (100 μmol)
Vinyl-4-benzylphenylketone (15.3 mg) and isopropylbenzylamine (10.2 mg) were heated at 45° C. for 5 hours.
NMR (CDCl3) 1.05 (m, 6H), 2.4 (m, 2H), 2.7 (m, 2H), 2.9 (m, 1H), 3.7 (m, 2H), 4.0 (s, 2H), 7.2-7.8 (m, 14H)
TG 79.3 (3 μmol) 46.3 (10 μmol) 18.5 (30 μmol)
SOCE 10 (10 μmol) 50 (30 μmol) 60 (100 μmol)
IICR 80 (10 μmol) 80 (30 μmol) 100 (100 μmol)
Vinyl-4-benzylphenylketone (15.3 mg) and methylbenzylamine (8.2 mg) were heated at 45° C. for 5 hours.
NMR (CDCl3) 2.4 (m, 2H), 2.7 (m, 2H), 3.7 (m, 2H), 3.8 (m, 3H), 4.0 (m, 2H), 7.1-7.8 (m, 14H)
TG 95 (3 μmol) 82 (10 μmol 44 (30 μmol)
SOCE 0 (10 μmol) 10 (30 μmol) 70 (100 μmol)
IICR 40 (10 μmol) 20 (30 μmol 90 (100 μmol
Vinyl-4-benzylphenylketone (15.3 mg) and t-butylbenzylamine (12.2 mg) were heated at 45° C. for 5 hours.
NMR (CDCl3) 1.25 (s, 9H), 2.4 (m, 2H), 2.7 (m, 2H), 3.7 (m, 2H), 4.0 (m, 2H), 7.1-7.8 (m, 14H)
TG 63.3 (3 μmol) 36.2 (10 μmol) 23.6 (30 μmol)
SOCE 0 (10 μmol) 20 (30 μmol) 40 (100 μmol)
IICR 40 (10 μmol) 70 (30 μmol) 90 (100 μmol)
Acetylpyridine (121 mg), propylbenzylamine (149 mg), and paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 1.05 (m, 6H), 2.6 (m, 2H), 2.7 (m, 2H), 2.9 (m, 1H), 3.7 (m, 2H), 7.0-9.1 (m, 9H)
TG 57.4 (0.3 μmol) 19.4 (1 μmol) 23.4 (3 μmol) 8.7 (10 μmol) 6.0 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 90 (10 μmol) 90 (30 μmol) 100 (100 μmol)
Acetylpyridine (121 mg), isopropylbenzylamine (163 mg), and paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 1.05 (m, 6H), 2.5-2.7 (m, 2H), 2.8 (m, 2H), 3.0 (m, 1H), 3.7 (m, 2H), 7.1-7.6 (7H), 7.8 (2H)
TG 10.4 (3 μmol) 6.5 (10 μmol) 6.3 (30 μmol)
SOCE 0 (10 μmol) 20 (30 μmol) 30 (100 μmol)
IICR 30 (10 μmol) 90 (30 μmol) 90 (100 μmol)
Acetylpyrazine (122 mg), 2-hydroxyethylbutyl amine (105 mg), and paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 0.8 (s, 3H), 1.5 (m, 4H), 2.4 (m, 2H), 2.7 (m, 2H), 2.9 (m, 2H), 3.5 (m, 2H), 3.7 (m, 2H), 8.72 (s, 1H), 8.75 (s, 1H), 9.21 (m, 1H)
TG 29.6 (3 μmol) 2.6 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 0 (10 μmol) 10 (30 μmol) 80 (100 μmol)
Acetylfuran (121 mg), isopropylbenzylamine (163 mg), and paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 0.9-1.1 (m, 6H), 2.45 (m, 2H), 2.8 (m, 2H), 2.9 (m, 1H), 3.7 (m, 2H), 7.0-7.6 (m, 8H)
TG 71 (0.3 μmol) 40 (1 μmol) 13.8 (3 μmol) 14.5 (10 μmol) 17.5 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 10 (100 μmol)
IICR 20 (10 μmol) 90 (30 μmol) 70 (100 μmol)
Acetyl pyrrole (109 mg), N-isopropylbenzylamine (149 mg), and paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 140° C. for 2 hours.
NMR (CDCl3) 1.05 (m, 6H), 2.4 (m, 2H), 2.9 (m, 3H), 3.7 (m, 2H), 7.0-8.0 (m, 8H)
TG 92 (3 μmol) 91.2 (10 μmol) 85.9 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 20 (10 μmol) 40 (30 μmol) 100 (100 μmol)
Acetylpyrazine (122 mg), ethylbenzylamine (135 mg), and paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 140° C. for 2 hours.
NMR (CDCl3) 0.8 (s, 3H), 2.5-2.7 (m, 2H), 3.3 (m, 2H), 3.6 (m, 2H), 6.9-7.1 (m, 6H), 8.6 (s, 1H), 9.1 (s, 1H)
TG 14 (3 μmol) 4.2 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 30 (10 μmol) 80 (30 μmol) 95 (100 μmol)
1-acryloyldiphenylether (12.3 mg) and cysteamine (4.3 mg) were reacted at 50° C. for 5 hours.
NMR (CDCl3) 2.9-3.2 (m, 4H), 3.3 (m, 2H), 3.4 (m, 2H), 6.8-8.0 (9H)
TG 71.4 (3 μmol 47.1 (10 μmol) 20.3 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 30 (100 μmol)
IICR 20 (10 μmol) 30 (30 μmol) 40 (100 μmol)
1-acryloyldiphenylether (11.3 mg) and histamine (5.6 mg) were reacted at 50° C. for 5 hours.
NMR (CDCl3) 2.9-3.2 (m, 2H), 3.5 (m, 2H), 3.7 (m, 2H), 3.8 (m, 2H), 6.8-8.0 (m, 11H)
TG 72.6 (3 μmol) 34.2 (10 μmol) 4.0 (30 μmol)
SOCE 0 (10 μmol) 10 (30 μmol) 40 (100 μmol)
IICR 70 (10 μmol) 90 (30 μmol 100 (100 μmol)
1-acryloyldiphenylether (12.3 mg) and butylethanol amine (6.63 mg) were reacted at 50° C. for 5 hours.
NMR (CDCl3) 1.4-1.7 (m, 7H), 2.4 (m, 2H), 2.7 (m, 2H), 3.02 (m, 2H), 3.7 (m, 2H), 7.4-8.3 (m, 9H)
TG 73.9 (3 μmol) 44.4 (10 μmol) 3.7 (30 μmol)
SOCE 0 (10 μmol) 10 (30 μmol) 40 (100 μmol)
IICR 70 (10 μmol) 100 (30 μmol) 30 (100 μmol)
1-acryloyldiphenylether (12.3 mg) and furoylpiperazine (10 mg) were reacted at 50° C. for 5 hours.
NMR (CDCl3) 12.5 (m, 2H), 3.1 (m, 2H), 3.8 (m, 8H), 6.5-8.0 (12H)
TG 84 (3 μmol) 89 (10 μmol) 28.8 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 30 (100 μmol)
IICR 20 (10 μmol 20 (30 μmol 20 (100 μmol)
1-acryloyldiphenylether (12.3 mg) and diethyl amine (4.3 mg) were reacted at 50° C. for 5 hours.
NMR (CDCl3) 1.50 (m, 6H), 3.0 (m, 4H), 3.4 (m, 2H), 7.0-8.0 (m, 9H)
TG 84.8 (3 μmol) 65.1 (10 μmol) 14.1 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 20 (100 μmol)
IICR 20 (10 μmol) 20 (30 μmol) 70 (100 μmol)
Acetylpyrazine (61 mg), N-isopropylbenzylamine (75 mg), and paraformaldehyde (20 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 1.05 (m, 6H), 2.7 (m, 2H), 2.9 (m, 2H), 2.9 (m, 1H), 3.7 (m, 2H), 7.0-8.8 (m, 8H)
TG 32.9 (3 μmol) 12.4 (10 μmol) 0.7 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 20 (10 μmol) 50 (30 μmol) 90 (100 μmol)
Acetyl naphthalene (170 mg), diaminobutane (88 mg), and paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 1.3 (m, 4H), 1.8 (m, 4H), 3.0 (m, 2H), 3.0 (m, 1H), 3.7 (m, 2H), 6.5 (1H), 7.1 (1H), 7.2 (1H)
TG 100 (3 μmol) 88.6 (10 μmol) 56.1 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
Acetyl naphthalene (170 mg), spermidine (145 mg), and paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 1.60 (m, 4H), 2.54 (m, 4H), 2.6 (m, 2H), 2.8 (m, 2H), 3.2 (m, 2H), 3.4 (m, 2H), 3.6 (m, 2H), 7.5-8.2 (7H)
TG 100 (3 μmol) 72.4 (10 μmol) 31.7 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
Acetyl thiazole (64 mg), N-isopropylbenzylamine (75 mg), and paraformaldehyde (18 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 1.05 (m, 6H), 2.4 (m, 2H), 2.7 (m, 2H), 2.9 (m, 1H), 3.7 (m, 2H), 7.0-8.0 (m, 7H)
TG 47.5 (3 μmol) 23.5 (10 μmol) 1.7 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 20 (100 μmol)
IICR 10 (10 μmol) 90 (30 μmol) 100 (100 μmol)
Acetylfuran (110 mg), N-t-butylbenzylamine (163 mg), and paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 1.2 (m, 9H), 2.4 (m, 2H), 2.7 (m, 2H), 3.7 (m, 2H), 7.0-8.0 (m, 8H)
TG 70 (0.3 μmol) 38 (1 μmol) 13.3 (3 μmol) 0.2 (10 μmol) 1.7 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 10 (10 μmol) 50 (30 μmol) 100 (100 μmol)
Acetyl thiazole (127 mg), N-t-butylethanol amine (117 mg), and paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 130° C. for 2 hours.
NMR (CDCl3) 1.0 (m, 9H), 3.0 (m, 2H), 3.6 (m, 4H), 6.8 (m, 1H), 8.2 (m, 1H)
TG 102 (3 μmol) 68 (30 μmol)
SOCE 0 (10 μmol 0 (30 μmol) 0 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
Acetylfuran (110 mg), N-t-butylethanol amine (117 mg), and paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 1.05 (m, 6H), 2.5 (m, 2H), 3.0 (m, 2H), 3.0 (m, 2H), 3.6 (m, 2H), 6.6 (1H), 7.2 (1H), 7.6 (1H)
TG 57.9 (3 μmol) 25.5 (10 μmol) 9.2 (30 μmol)
SOCE 0 (10 μmol) 10 (30 μmol) 20 (100 μmol)
IICR 20 (10 μmol) 20 (30 μmol) 70 (100 μmol)
Acetylfuran (110 mg), benzylethanol amine (151 mg), and paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 2.5 (m, 2H), 3.0 (m, 2H), 3.7 (m, 2H), 3.8 (m, 2H), 4.2 (m, 2H), 6.6 (1H), 7.2 (1H), 7.1-7.6. (1H), 7.2-7.4 (5H)
TG 31.6 (3 μmol) 23 (10 μmol) 6.8 (30 μmol)
SOCE 0 (10 μmol 0 (30 μmol) 0 (100 μmol)
IICR 20 (10 μmol) 20 (30 μmol) 70 (100 μmol)
Acetylthiophene (126 mg), methylbenzylamine (121 mg), paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 2.2 (m, 3H), 2.5 (m, 2H), 3.1 (m, 2H), 3.7 (m, 2H), 7.0-7.7 (8H)
TG 78.9 (3 μmol) 62.2 (10 μmol) 19.0 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 0 (10 μmol) 30 (30 μmol) 70 (100 μmol)
Acetylthiophene (126 mg), methylethanol amine (75 mg), and paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 2.5 (s, 3H), 2.7 (m, 2H), 3.7 (m, 2H), 3.8 (m, 2H), 7.2 (1H), 6.5 (1H), 6.7 (1H)
TG 57 (3 μmol) 30 (10 μmol) 4.8 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 20 (10 μmol) 20 (30 μmol) 70 (100 μmol)
Acetylthiophene (126 mg), 2-piperidine methanol (115 mg), and paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 1.5 (m, 6H), 2.3 (m, 4H), 2.6 (m, 2H), 3.0 (m, 2H), 3.6 (m, 2H), 7.2 (H), 7.6-7.7 (2H)
TG 67.7 (3 μmol) 25.7 (10 μmol) 3.4 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 10 (100 μmol)
IICR 20 (10 μmol) 20 (30 μmol) 50 (100 μmol)
Acetylthiophene (126 mg), aminothiophenol (125 mg), and paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 2.5 (m, 2H), 2.7 (m, 2H), 7.1 (1H), 7.6 (1H), 7.7 (1H))
TG 91.5 (3 μmol) 86.3 (10 μmol) 70.5 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 20 (100 μmol)
IICR 0 (10 μmol) 30 (30 μmol) 10 (100 μmol)
Acetylpyrazine (122 mg), benzylethanol amine (157 mg), and paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 2.6 (m, 2H), 3.0 (m, 2H), 3.7 (m, 2H), 3.8 (m, 2H), 7.2-7.4 (5H), 8.6 (s, 1H), 8.7 (s, 1H), 9.2 (s, 1H))
TG 68 (1 μmol) 37.3 (3 μmol) 8.0 (10 μmol) 10.8 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 0 (10 μmol) 50 (30 μmol) 90 (100 μmol)
Acetylfuran (110 mg), diethanol amine (105 mg), and paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 2.4-2.6 (m, 4H), 2.8 (m, 2H), 3.4-3.7 (m, 4H), 3.7 (m, 2H), 6.5 (1H), 7.1 (1H), 7.5 (1H)
TG 60 (1 μmol) 16.8 (3 μmol) 6.4 (10 μmol) 1.9 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 20 (10 μmol) 20 (30 μmol) 50 (100 μmol)
Acetophenone (120 mg), N-methylpiperazine (100 mg), and paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 2.5 (m, 2H), 3.0 (m, 4H), 3.0 (m, 2H), 3.6 (m, 2H), 6.6 (1H), 6.5 (1H), 7.1-7.2.0 (7H)
TG 100 (3 μmol) 92.2 (10 μmol) 83.1 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 30 (10 μmol) 20 (30 μmol) 50 (100 μmol)
Acetylfuran (110 mg), anilinoethanol (137 mg), and paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 2.5 (m, 2H), 3.0 (m, 4H), 3.0 (m, 2H), 3.6 (m, 2H), 6.6 (1H), 6.5 (1H), 7.1-7.2.0 (7H)
TG 100 (3 μmol) 99 (10 μmol) 67 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 10 (10 μmol) 20 (30 μmol) 20 (100 μmol)
Acetophenone (111 mg), 2-anilinoethanol (137 mg), and paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 2.5 (m, 2H), 3.0 (m, 4H), 3.0 (m, 2H), 3.6 (m, 2H), 6.6 (1H), 6.5 (1H), 7.1-7.2.0 (7H).
TG 100 (3 μmol) 92.2 (10 μmol) 90 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 20 (10 μmol) 20 (30 μmol) 30 (100 μmol)
Acetylpyridine (121 mg), 2-anilinoethanol (146 mg), and paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 2.5 (m, 2H), 3.0 (m, 4H), 3.0 (m, 2H), 3.6 (m, 2H), 6.6 (1H), 6.5 (1H), 7.1-7.2.0 (7H)
TG 63.6 (3 μmol) 42.0 (10 μmol) 10.9 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 20 (10 μmol) 20 (30 μmol) 30 (100 μmol)
4-acetylpyridine (243 mg), benzylhydroxyethyl amine (302 mg), and paraformaldehyde (80 mg) were reacted in dioxane (0.4 ml) at 130° C. for 2 hours.
NMR (CDCl3) 2.60 (m, 2H), 3.0 (m, 2H), 3.6 (m, 2H), 4.3 (m, 2H), 7.1 (m, 1H), 7.3 (m, 5H), 7.7 (s, 1H), 8.8 (s, 1H)
TG 64 (3 μmol) 42 (10 μmol) 11 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 20 (10 μmol) 10 (30 μmol) 0 (100 μmol)
4-methyl-acetylfuran (124 mg), isopropylbenzylamine (144 mg), and paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 1.05 (m, 6H), 2.1 (m, 2H), 2.8 (m, 2H), 3.0 (m, 1H), 3.7 (m, 2H), 6.1 (111), 7.1-7.5 (m, 7H)
TG 13.6 (3 μmol) 11.0 (10 μmol) 0 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 20 (100 μmol)
IICR 50 (10 μmol) 60 (30 μmol) 80 (100 μmol)
4-methyl-acetylfuran (124 mg), N-t-butylbenzylamine (163 mg), and paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 1.1 (m, 9H), 2.1 (s, 3H), 2.5 (m, 2H), 2.8 (m, 2H), 3.7 (m, 2H), 6.1 (1H), 7.0-7.2 (6H)
TG 42.8 (3 μmol) 16.4 (10 μmol) 5.8 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 40 (10 μmol) 50 (30 μmol) 50 (100 μmol)
4-methyl-acetylfuran (124 mg), dibenzylamine (198 mg), and paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 2.1 (m, 3H), 2.5 (m, 2H), 3.4 (m, 2H), 3.7 (m, 4H), 7.3-7.5 (m, 12H)
TG 77.3 (3 μmol) 46.1 (10 μmol) 17.4 (30 μmol)
SOCE 0 (10 μmol) 10 (30 μmol) 20 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 10 (100 μmol
4-methyl-acetylfuran (124 mg), hydroxyethylbenzylamine (154 mg), and paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 2.1 (m, 3H), 2.5 (m, 2H), 2.9 (m, 2H), 3.7 (m, 2H), 3.8 (m, 2H), 4.3 (m, 2H), 6.2 (s, 1H), 7.1 (m, 1H), 7.2-7.5 (m, 5H)
TG 68.6 (3 μmol) 31.7 (10 μmol) 5.6 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 20 (10 μmol) 20 (30 μmol) 30 (100 μmol)
4-methyl-acetylfuran (124 mg), hydroxyethylmethyl amine (76 mg), and paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 2.1 (m, 3H), 2.3 (m, 2H), 3.0 (m, 2H), 3.6 (m, 2H), 6.6 (1H), 7.0 (1H)
TG 67 (1 μmol) 32.3 (3 μmol) 11.9 (10 μmol) 4.4 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol 0 (100 μmol)
IICR 20 (10 μmol) 20 (30 μmol) 30 (100 μmol)
1-acetyl naphthalene (170 mg), 2-amino-2-ethyl-1,3-propanediol (161 mg), and paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 0.9 (m, 3H), 2.5 (m, 2H), 3.6 (m, 2H), 3.7 (m, 2H), 4.4 (m, 4H), 7.4-8.0 (7H)
TG 81.5 (3 μmol) 80.2 (10 μmol) 61.6 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 20 (10 μmol) 20 (30 μmol) 20 (100 μmol)
2-acetylfuran (121 mg), ethylbenzylamine (140 mg), and paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 1.05 (m, 3H), 2.5 (m, 2H), 2.9 (m, 2H), 3.5 (m, 2H), 3.7 (m, 2H), 6.5 (1H), 7.2-7.2 (7H)
TG 24.8 (3 μmol) 10.8 (10 μmol) 6.9 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 40 (10 μmol) 50 (30 μmol) 80 (100 μmol)
2-acetyl thiazole (50 mg), diethanol amine (44 mg), and paraformaldehyde (10 mg) were reacted at 130° C. for 1 hour.
NMR (CDCl3) 2.5-2.8 (m, 6H), 3.5-3.9 (m, 6H), 7.6-8.1 (m, 2H)
TG 66 (3 μmol) 10 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 10 (100 μmol
IICR 0 (10 μmol) 50 (30 μmol) 90 (100 μmol)
3-acetylpyridine (121 mg), ethylbenzylamine (135 mg), and paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 0.9-1.0 (m, 3H), 2.3-2.8 (m, 4H), 3.4 (m, 2H), 3.7 (m, 2H), 7.0-7.8 (m, 8H), 8.8 (1H)
TG 32.6 (3 μmol) 10.2 (10 μmol) 10.4 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 30 (10 μmol) 40 (30 μmol) 50 (100 μmol)
4-methyl-acetylfuran (124 mg), bishydroxyethyl amine (125 mg), and paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 2.15-2.4 (m, 4H), 2.4-2.4 (m, 2H), 3.5-3.9 (m, 4H), 4.2 (m, 2H), 6.1 (1H), 7.2 (1H)
TG 62.9 (3 μmol) 45.3 (10 μmol) 13.1 (30 μmol)
SOCE 0 (10 μmol) 10 (30 μmol) 20 (100 μmol)
IICR 50 (10 μmol) 30 (30 μmol) 30 (100 μmol)
4-methyl-acetylfuran (124 mg), isopropylaminoethanol (106 mg), paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 0.96 (m, 6H), 2.4 (m, 4H), 3.0 (m, 2H), 3.6 (m, 2H), 6.6 (1H), 7.1-7.2.0 (1H)
TG 36 (3 μmol) 15 (10 μmol) 5 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 50 (10 μmol) 30 (30 μmol) 90 (100 μmol)
2-acetyl naphthalene (167 mg), diethanol amine (102 mg), and paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 2.6 (m, 4H), 3.0 (m, 2H), 3.6 (m, 2H), 3.8 (m, 2H), 7.6-8.1 (7H)
TG 76.2 (3 μmol) 63.3 (10 μmol 30.3 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 20 (10 μmol) 60 (30 μmol) 90 (100 μmol)
4-methoxyacetophenone (171 mg), diethanol amine (102 mg), and paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 2.4-2.6 (m, 4H), 2.8 (m, 2H), 3.4-3.7 (m, 4H), 3.7 (s, 3H), 7.0 (m, 2H), 7.95 (m, 2H)
TG 115 (3 μmol) 105 (10 μmol) 58 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 20 (10 μmol) 30 (30 μmol) 90 (100 μmol)
Acetylthiophene (134 mg), diethanol amine (112 mg), and paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 2.4-2.6 (m, 4H), 2.8 (m, 2H), 3.4-3.7 (m, 4H), 3.7 (m, 2H), 6.5 (1H), 7.1 (1H), 7.2 (1H)
TG 84.1 (3 μmol) 60.6 (10 μmol) 24.3 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 20 (10 μmol) 20 (30 μmol) 80 (100 μmol)
3-acetylpyridine (126 mg), diethanol amine (114 mg), and paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 2.5 (m, 2H), 2.8 (m, 4H), 3.6 (m, 4H), 4.0 (m, 2H), 7.4 (1H) 8.2 (1H), 8.6-9.2 (2H)
TG 103.4 (3 μmol) 83.4 (10 μmol) 57.4 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 10 (100 μmol)
IICR 30 (10 μmol) 20 (30 μmol) 50 (100 μmol)
Acetylpyrazine (122 mg), isopropylethanol amine (111 mg), and paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 1.1-1.2 (m, 6H), 2.1 (m, 2H), 2.7 (m, 4H), 3.8 (m, 2H), 8.6-9.3 (m, 3H)
TG 64.0 (3 μmol) 46.9 (10 μmol 18.0 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol 0 (100 μmol)
IICR 20 (10 μmol) 20 (30 μmol) 50 (100 μmol
4-methyl-acetylfuran (124 mg), benzylamine (107 mg), and paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 2.2-2.5 (m, 5H), 3.4 (m, 2H), 3.6 (m, 2H), 6.1 (1H), 7.1-7.5 (6H)
TG 83.3 (3 μmol 86.4 (10 μmol) 81.4 (30 μmol
SOCE 0 (10 μmol 10 (30 μmol 30 (100 μmol)
IICR 20 (10 μmol) 10 (30 μmol) 30 (100 μmol)
Acetylfuran (110 mg), isopropylethanol amine (111 mg), and paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 1.05 (m, 6H), 2.5 (m, 2H), 2.9 (m, 2H), 3.9 (m, 2H), 4.2 (m, 2H), 6.6 (1H), 6.5 (1H), 7.1-7.2 (1H)
TG 25.1 (3 μmol) 6.4 (10 μmol) 8.3 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 10 (100 μmol)
IICR 50 (20 μmol) 60 (30 μmol) 80 (100 μmol)
Acetylpyridine (121 mg), isopropylethanol amine (111 mg), and paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 1.05 (m, 6H), 2.6 (m, 2H), 2.7 (m, 2H), 3.4 (m, 2H), 3.8 (m, 2H), 7.5 (1H), 7.9 (1H), 8.0 (1H), 8.7 (m, 1H)
TG 60.6 (3 μmol) 44.5 (10 μmol) 12.9 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 40 (10 μmol) 20 (30 μmol) 80 (100 μmol)
4-acetylpyridine (121 mg), isopropylethanol amine (111 mg), and paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 1.1 (m, 6H), 2.6 (m, 4H), 2.8 (m, 2H), 3.6 (m, 2H), 7.2 (2H), 7.8 (2H)
TG 60 (3 μmol) 37 (10 μmol) 9.4 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 20 (10 μmol) 50 (30 μmol) 80 (100 μmol)
Acetyl thiazole (63 mg), isopropylethanol amine (52 mg), and paraformaldehyde (20 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3), 0.9-1.2 (m, 6H), 2.7 (m, 2H), 3.0 (m, 4H), 3.4 (m, 1H), 3.8 (m, 2H), 7.7 (1H), 8.1 (1H).
TG 80.9 (3 μmol) 68.4 (10 μmol) 26.0 (30 μmol)
SOCE 0 (10 μmol) 10 (30 μmol) 20 (100 μmol)
IICR 20 (10 μmol) 30 (30 μmol) 60 (100 μmol)
4-fluoropropiophenone (152 mg), isopropylethanol amine (103 mg), and paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 1.05 (m, 6H), 1.2 (m, 3H), 2.0-2.5 (m, 2H), 2.8-3.0 (m, 3H), 3.5-3.6 (m, 2H), 6.5 (1H), 7.2 (2H), 7.9. (2H)
TG 104.6 (3 μmol) 107.1 (10 μmol) 84.8 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
3-acetylpyridine (363 mg), isopropylethanol amine (309 mg), and paraformaldehyde (110 mg) were reacted in dioxane (0.6 ml) at 150° C. for 2 hours.
NMR (CDCl3) 1.05 (m, 6H), 2.5 (m, 4H), 3.0 (m, 2H), 3.0 (m, 1H), 3.7 (m, 2H), 6.5 (1H), 6.8 (1H), 8.6 (1H), 9.0 (1H).
TG 92 (3 μmol) 55 (10 μmol) 11.4 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 30 (10 μmol) 20 (30 μmol) 20 (100 μmol)
4-fluoropropiophenone (152 mg), benzylethanol amine (103 mg), and paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 1.28 (m, 3H), 2.5 (m, 2H), 3.4 (m, 2H), 3.5 (m, 2H), 4.0 (m, 2H), 7.1-7.2.0 (7H), 8.0 (m, 2H)
TG 100 (3 μmol) 100 (10 μmol) 92 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 20 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 20 (100 μmol)
4-fluoropropiophenone (152 mg), diethanol amine (105 mg), paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 1.25 (m, 3H), 2.5 (m, 2H), 3.0 (m, 4H), 3.0 (m, 2H), 3.6-3.7 (m, 4H), 6.9-7.2 (2H), 7.9-8.1 (2H)
TG 92 (3 μmol) 113 (10 μmol) 103 (30 μmol)
SOCE 0 (10 μmol) 20 (30 μmol) 60 (100 μmol)
IICR 0 (10 μmol 0 (30 μmol) 20 (100 μmol)
4-fluoropropiophenone (152 mg), t-butylethanol amine (103 mg), and paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 1.05 (m, 6H), 2.5 (m, 2H), 3.0 (m, 2H), 3.0 (m, 1H), 3.7 (m, 2H), 6.5 (1H), 7.1 (1H), 7.2.0 (1H)
TG 100 (3 μmol) 106 (10 μmol) 88 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 20 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 20 (100 μmol)
4-fluoropropiophenone (152 mg), t-butylbenzylamine (163 mg), and paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 1.2 (m, 9H), 1.3 (m, 3H), 2.0 (m, 2H), 3.8 (m, 2H), 6.8-8.1 (9H)
TG 100 (3 μmol) 104 (10 μmol) 87 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 40 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
4-fluoropropiophenone (152 mg), methylethanol amine (73 mg), and paraformaldehyde (40 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 1.3 (m, 3H), 2.3 (m, 3H), 2.5 (2H), 3.0 (m, 2H), 3.6 (m, 2H), 6.6 (2H), 7.1-7.20 (2H)
TG 100 (3 μmol) 100 (10 μmol 91 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 20 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
2-acetyl-1-methylpyrrole (62 mg), hydroxyethylbenzylamine (76 mg), paraformaldehyde (18 mg) were reacted in dioxane (0.1 ml) at 150° C. for 2 hours.
NMR (CDCl3) 2.7 (m, 2H), 3.0 (m, 2H), 3.6-3.8 (m, 6H), 4.3 (s, 3H), 7.2 (m, 5H)
TG 107 (3 μmol) 91.3 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 10 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 40 (100 μmol)
2-acetyl-1-methylpyrrole (62 mg), t-butylbenzylamine (81 mg), and paraformaldehyde (18 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 1.0 (s, 9H), 2.33 (m, 2H), 3.64 (m, 2H), 3.83 (m, 2H), 6.0 (s, 1H), 6.6 (s, H), 6.7 (s, 1H), 7.24 (m, 5H)
TG 114 (3 μmol) 100 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
4-fluoroacetophenone (138 mg), hydroxyethylisopropylamine (103 mg), and paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 1.05 (m, 6H), 2.5 (m, 4H), 3.0 (m, 2H), 3.0 (m, 1H), 3.7 (m, 2H), 7.2 (2H), 8.0 (2H)
TG 97 (3 μmol) 67 (10 μmol) 35.5 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 20 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
2-acetyl-1-methylpyrrole (62 mg), hydroxyethylmethyl amine (41 mg), and paraformaldehyde (18 mg) were reacted in dioxane (0.1 ml) at 150° C. for 2 hours.
NMR (CDCl3) 2.4-2.8 (m, 6H), 3.8-4.1 (m, 5H), 6.0 (s, 1H), 6.6-6.7 (m, 2H),
TG 104 (3 μmol) 100 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
Phenacyl chloride (154 mg), isopropylbenzylamine (149 mg), and diisopropylethyl amine (128 mg) were reacted in dioxane (0.1 ml) at 100° C. for 2 hours.
NMR (CDCl3) 1.05 (m, 6H), 2.5 (m, 2H), 3.0 (m, 1H), 3.7 (m, 2H), 7.2-8.0 (10H)
TG 77 (3 μmol) 41.6 (10 μmol) 10.6 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 50 (100 μmol)
IICR 0 (10 μmol 0 (30 μmol) 70 (100 μmol)
2-acetyl-1-methylpyrrole (62 mg), hydroxyethylisopropylamine (53 mg), and paraformaldehyde (20 mg) were reacted in dioxane (0.1 ml) at 150° C. for 2 hours.
NMR (CDCl3) 10 (m, 6H), 2.4 (m, 2H), 2.9 (m, 2H), 3.9 (m, 2H), 4.0 (m, 3H), 4.3 (m, 2H), 5.15, 6.8, 6.95
TG 107 (3 μmol) 95 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
2-acetyl pyrrole (109 mg), hydroxyethylisopropylamine (107 mg), and paraformaldehyde (40 mg) were reacted in dioxane (0.1 ml) at 150° C. for 2 hours.
NMR (CDCl3) 1.60 (m, 6H), 2.35 (m, 2H), 2.83 (m, 2H), 3.78 (m, 2H), 4.23 (m, 2H), 6.16, 6.84, 6.97
TG 103 (3 μmol) 85.2 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
Acryloyl chloride (0.45 g), furan (0.34 g), and AlCl3 (0.66 g) were reacted in CH2Cl2 at −60° C.
NMR (CDCl3) 5.2 (m, 1H), 5.4 (m, 1H), 6.0 (m, 1H), 6.2-6.5 (m, 1H), 7.2 (m, 1H) 7.5 (m, 1H)
TG 96 (3 μmol) 97 (10 μmol) 7.4 (30 μmol)
SOCE 0 (10 μmol) 10 (30 μmol) 30 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
2-furyl vinylketone (36 mg) and isopropylhydroxyethyl amine (30 mg) were mixed with dichlormethane (0.5 mL). The resultant was left for 2 hours.
NMR (CDCl3) 1.4 (m, 6H), 2.2 (m, 2H), 2.8 (m, 2H), 3.4 (m, 2H), 3.8 (m, 2H), 6.5 (1H), 7.1 (1H), 7.2 (1H)
TG 70.6 (3 μmol) 104 (10 μmol) 77.7 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
NMR (CDCl3) 2.42 (m, 2H), 2.73 (m, 2H), 2.97 (m, 2H), 3.70-90 (m, 4H), 4.31 (2H), 5.29 (m, 1H), 6.24 (m, 1H), 7.0 (m, 1H), 7.31 (m, 5H)
TG 107 (3 μmol) 91.3 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 0 (10 μmol) 50 (30 μmol) 80 (100 μmol)
2-acryloylfuran (29 mg) and diethanol amine (24 mg) were reacted in dioxane (0.2 ml) at 50° C. for 2 hours.
NMR (CDCl3) 3.0 (m, 4H), 3.7 (m, 4H), 3.8 (m, 2H), 6.2 (1H), 6.4 (1H), 7.1-7.2 (1H)
TG 88 (3 μmol) 79.0 (10 μmol) 51.6 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
2-acetyl pyrrole (112 mg), benzylmethyl amine (125 mg), and paraformaldehyde (40 mg) were reacted in dioxane (0.2 ml) at 130° C. for 2 hours.
NMR (CDCl3) 2.12 (m, 2H), 2.40 (m, 2H), 8.8 (m, 5H), 6.10 (s, 1H), 7.60 (s, 1H), 7.3 (m, 5H)
TG 99.9 (3 μmol) 108 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 10 (10 μmol) 10 (30 μmol) 20 (100 μmol)
3-acetylpyridine (6.5 mg), histamine (6 mg), and paraformaldehyde (2 mg) were reacted in dioxane (0.1 ml) at 150° C. for 2 hours.
NMR (CDCl3) 2.10 (m, 2H), 2.18 (m, 2H), 3.50 (m, 2H), 3.60 (m, 2H), 7.0-7.8 (m, 61-1)
TG 100 (3 μmol) 88 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 10 (10 μmol) 30 (30 μmol) 50 (100 μmol
3-acetylpyridine (121 mg), hydroxyethylbenzylamine (156 mg), and paraformaldehyde (40 mg) were reacted in dioxane (0.2 ml) at 130° C. for 2 hours.
NMR (CDCl3) 2.6 (m, 2H), 3.6 (m, 2H), 3.7 (m, 2H), 3.9 (m, 2H), 4.3 (m, 2H), 7.2 (s, 1H), 7.4 (m, 5H), 8.2 (s, H), 8.8 (s, 1H), 9.1 (s, 1H)
TG 84.6 (3 μmol) 8.8 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 50 (100 μmol)
Chlorobutyrophenone (10.9 mg), hydroxyethylisopropylamine (3.8 mg), and diisopropylethyl amine (4 mg) were reacted in dioxane (0.2 ml) at 50° C. for 2 hours.
NMR (CDCl3) 2.5 (m, 2H), 3.0 (m, 4H), 3.0 (m, 2H), 3.6 (m, 2H), 6.6 (1H), 6.5 (1H), 7.1-7.2.0 (7H)
TG 107 (3 μmol) 100 (10 μmol) 60.3 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
4-chlorobutyrophenone (10 mg), isopropylbenzylamine (3.8 mg), and diisopropylethanol amine (4.7 mg) at 100° C. for 1.5 hours.
NMR (CDCl3) 1.05 (m, 6H), 2.3 (m, 4H), 3.2 (m, 2H), 3.0 (m, 1H), 3.7 (m, 2H), 6.5 (1H), 7.5-80 (10H)
TG 107 (3 μmol) 100 (10 μmol) 75 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
3-acetylpyridine (122 mg), hydroxyethylbutyl amine (115 mg), and paraformaldehyde (40 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 0.95 (s, 3H), 1.4 (m, 4H), 2.5 (m, 2H), 2.7 (m, 2H), 2.9 (m, 2H), 3.8 (m, 2H), 4.3 (m, 2H) 7.5, 8.2, 8.9, 9.1 (s, 1H)
TG 39.7 (3 μmol) 6.6 (10 μmol) −4.8 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 50 (100 μmol)
2-fluoropropylphenone (152 mg), hydroxyethylisopropylamine (103 mg), and paraformaldehyde (40 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 1.2 (m, 6H), 1.7 (m, 3H), 3.0 (m, 4H), 3.4 (m, 2H), 3.6 (m, 2H), 6.6 (1H), 7.0-7.8 (4H)
TG 108 (3 μmol) 91.3 (10 μmol) 67 (30 μmol
SOCE 20 (10 μmol) 40 (30 μmol) 80 (100 μmol)
IICR 0 (10 μmol) 10 (30 μmol) 20 (100 μmol)
2-fluoropropylphenone (152 mg), benzylisopropylamine (149 mg), and paraformaldehyde (40 mg) were reacted in dioxane (0.2 ml) at 150° C. for 2 hours.
NMR (CDCl3) 1.1 (m, 6H), 1.4 (m, 3H), 2.8 (m, 2H), 3.0 (m, 1H), 3.7 (m, 2H), 7.1-7.5 (m, 9H)
TG 100 (3 μmol) 96 (10 μmol) 74 (30 μmol)
SOCE 10 (10 μmol) 50 (30 μmol) 80 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 50 (100 μmol)
2-acetylthiophene (126 mg), benzylisopropylamine (149 mg), and paraformaldehyde (40 mg) were reacted in dioxane (0.2 ml) at 130° C. for 2 hours.
NMR (CDCl3) 1.1 (m, 6H), 2.6 (m, 2H), 2.9 (m, 2H), 3.6-3.8 (m, 3H), 7.0-7.8 (m, 8H)
TG 27.5 (3 μmol) 5.4 (10 μmol) 68.0 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 20 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 50 (100 μmol)
2-acetylthiophene (126 mg), benzylhydroxyethyl amine (151 mg), and paraformaldehyde (40 mg) were reacted in dioxane (0.2 ml) at 130° C. for 2 hours.
NMR (CDCl3) 2.55 (m, 2H), 3.0 (m, 2H), 3.7 (m, 2H), 3.8 (m, 2H), 4.35 (m, 2H), 7.1 (m, 6H), 7.55 (s, 1H), 8.0 (s, 1H)
TG 76.5 (3 μmol) 36.8 (10 μmol) 7.3 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 30 (10 μmol) 50 (30 μmol) 60 (100 μmol)
2-acetylpyridine (121 mg), diphenyl amine (169 mg), and paraformaldehyde (40 mg) were reacted in dioxane (0.2 ml) at 130° C. for 2 hours.
NMR (CDCl3) 2.8 (m, 4H), 6.8-7.4 (m, 10H), 7.4 (1H), 7.8. (1H), 8.1 (m, 1H), 8.7 (m, 1H)
TG 97.1 (3 μmol 114.6 (10 μmol 106.2 (30 μmol)
SOCE 0 (10 μmol) 10 (30 μmol) 20 (100 μmol)
IICR 0 (10 μmol) 10 (30 μmol) 20 (100 μmol)
2-acetyl-3-ethylpyrazine (151 mg), benzylisopropylamine (149 mg), and paraformaldehyde (40 mg) were reacted in dioxane (0.2 ml) at 130° C. for 2 hours.
NMR (CDCl3) 1.1-1.2 (m, 6H), 2.7 (m, 1H), 3.1 (m, 4H), 3.7 (m, 2H), 7-7.2 (m, 1H)
TG 29 (3 μmol) 16 (10 μmol) 14 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 10 (100 μmol)
IICR 70 (10 μmol) 90 (30 μmol) 100 (100 μmol)
2-acetyl-3-ethylpyrazine (150 mg), hydroxyethylisopropylamine (149 mg), and paraformaldehyde (40 mg) were reacted in dioxane (0.2 ml) at 130° C. for 2 hours.
NMR (CDCl3) 1.3 (m, 3H), 2.6 (m, 4H), 3.2 (m, 4H), 8.6 (s, 1H), 8.7 (s, 1H)
TG 90.3 (3 μmol) 73 (10 μmol) 30 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 10 (100 μmol)
IICR 20 (10 μmol) 10 (30 μmol) 100 (100 μmol)
2-acetyl-3-ethylpyrazine (151 mg), benzyl-t-butyl amine (149 mg), and paraformaldehyde (40 mg) were reacted in dioxane (0.2 ml) at 130° C. for 2 hours.
NMR (CDCl3) 1.1 (m, 9H), 2.7 (m, 1H), 3.1 (m, 4H), 3.7 (m, 2H), 7-7.1 (m, 1H), 8.5-8.6 (m, 1H)
TG 42 (3 μmol) 22 (10 μmol) 10 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 20 (100 μmol)
IICR 50 (10 μmol) 90 (30 μmol) 100 (100 μmol)
Acetophenone (120 mg), aminoadamantane HCl (187 mg), and paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 110° C. for 2 hours.
NMR (CDCl3) 1.8-2.1 (m, 12H), 3.4 (m, 2H), 3.95 (m, 2H), 7.2-9.4 (5H)
TG 116 (3 μmol) 105 (10 μmol) 83 (30 μmol)
SOCE 0 (10 μmol) 10 (30 μmol) 10 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
5-Methyl-2-acetylfuran (124 mg), aminoadamantane HCl (187 mg), and paraformaldehyde (120 mg) were reacted in 110° C. for 2 hours.
NMR (CDCl3) 1.7-2.2 (m, 16H), 3.4 (m, 2H), 3.6 (m, 2H), 6.1 (1H), 7.3 (1H)
TG 106 (3 μmol) 87.3 (10 μmol) 35.9 (30 μmol)
SOCE 0 (10 μmol) 10 (30 μmol) 50 (100 μmol)
IICR 0 (10 μmol) 10 (30 μmol) 50 (100 μmol)
The title compound was synthesized in the manner as described in Example 189.
NMR (CDCl3) 1.8 (m, 3H), 2.2 (m, 13H), 3.0 (m, 2H), 6.5 (2H), 7.1-8.2 (2H)
TG 111 (3 μmol) 124.4 (10 μmol) 113.1 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
The title compound was synthesized from chlorobutyryl chloride (141 mg), pyridine (2 ml), and AlCl3 (260 mg).
NMR (CDCl3) 2.1 (m, 2H), 2.2 (m, 2H), 2.6 (m, 2H), 3.7 (m, 2H), 7.7 (2H), 8.6 (2H)
TG 117 (3 μmol) 93 (10 μmol) 49 (30 μmol)
SOCE 0 (10 μmol) 10 (30 μmol) 20 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
2-acetylthiophene (127 mg), benzyl-t-butyl amine (169 mg), and paraformaldehyde (40 mg) were reacted in dioxane (0.2 ml) at 130° C. for 2 hours.
NMR (CDCl3) 1.1 (m, 9H), 2.7 (m, 2H), 3.0 (m, 2H), 3.8 (m, 2H), 7.0-7.4 (5H), 7.7 (2H)
TG 51.5 (0.3 μmol) 18.5 (1.0 μmol) 4.3 (3 μmol) −14.6 (10 μmol) −15.6 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol 0 (100 μmol
IICR 70 (10 μmol) 95 (30 μmol) 100 (100 μmol)
2-acetylthiophene (126 mg), 2-hydroxyethylisopropylamine (121 mg), and paraformaldehyde (40 mg) were reacted in dioxane (0.2 ml) at 130° C. for 2 hours.
NMR (CDCl3) 1.05 (m, 6H), 2.5 (m, 2H), 3.0 (m, 4H), 3.0 (m, 2H), 3.6 (m, 2H), 6.6 (1H), 6.5 (1H), 7.1-7.2.0 (7H)
TG 80.5 (3 μmol) 38.3 (10 μmol) −4.3 (30 μmol)
SOCE 0 (10 μmol 0 (30 μmol) 10 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
2-acetyl-1-methylpyrrole (123 mg), isopropylbenzylamine (149 mg), and paraformaldehyde (36 mg) were reacted at 70° C. for 10 minutes.
NMR (CDCl3) 1.05 (m, 6H), 2.5 (m, 2H), 3.0 (m, 3H), 3.5-3.8 (m, 2H), 3.7 (m, 2H), 7.0-7.5 (m, 6H), 7.7-8.0 (2H)
TG 73 (3 μmol) 62.6 (10 μmol) 6.4 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 10 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
4-fluorobromoacetophenone (217 mg), benzylisopropylamine (149 mg), paraformaldehyde (40 mg), and diisopropylethyl amine (128 mg) were reacted in dioxane (0.2 ml) at 130° C. for 2 hours.
NMR (CDCl3) 1.05 (m, 6H), 3.2 (m, 2H), 3.2 (m, 1H), 3.6 (m, 2H), 6.2-7.6 (9H)
TG 108 (3 μmol) 98 (10 μmol) 77.6 (30 μmol)
SOCE 0 (10 μmol) 20 (30 μmol) 40 (100 μmol)
IICR 0 (10 μmol) 10 (30 μmol) 30 (100 μmol)
Methyl vinylketone (106 mg) and isopropyl-2-hydroxyethyl amine (156 mg) were heated in hexane (0.5 ml) at 80° C. for 2 hours.
NMR (CDCl3) 1.1 (m, 6H), 2.1 (s, 3H), 2.6 (m, 2H), 2.8 (m, 2H), 2.9 (m, 1H), 3.5 (m, 2H), 3.85 (m, 2H)
TG 97 (3 μmol) 79 (10 μmol) 35.9 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
Methyl vinylketone (117 mg) and isopropylbenzylamine (246 mg) were heated in hexane (0.5 ml) at 30° C. for 2 hours.
NMR (CDCl3) 1.05 (m, 6H), 2.0 (m, 3H), 2.5 (m, 2H), 2.8 (m, 2H), 2.85 (m, 1H), 3.6 (m, 2H), 7.3 (5H)
TG 87 (3 μmol) 66 (10 μmol) 29.2 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
3-acetyl imidazole (110 mg), hydroxyethylisopropylamine (103 mg), and paraformaldehyde (40 mg) were reacted in dioxane (0.2 ml) at 130° C. for 2 hours.
NMR (CDCl3) 1.05 (m, 6H), 2.2 (m, 2H), 2.8 (m, 2H), 3.0 (m, 2H), 3.7 (m, 2H), 6.9 (1H), 7.1-7.6 (2H)
TG 104.9 (3 μmol) 127.1 (10 μmol) 132.2 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 10 (10 μmol) 20 (30 μmol) 0 (100 μmol)
N-acetylcaprolactam (153 mg), benzylisopropylamine (149 mg), and paraformaldehyde (40 mg) were reacted in dioxane (0.2 ml) at 130° C. for 2 hours.
NMR (CDCl3) 1.05 (m, 6H), 1.7 (m, 6H), 2.0 (m, 2H), 2.5 (m, 2H), 2.8 (m, 2H), 2.85 (m, 2H), 3.8 (m, 2H), 7.2 (5H)
TG 101.2 (3 μmol) 83.7 (10 μmol) 47.9 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 10 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 20 (100 μmol)
N-acetylcaprolactam (153 mg), isopropyl-2-hydroxyethyl amine (149 mg), and paraformaldehyde (40 mg) were reacted in dioxane (0.2 ml) at 130° C. for 2 hours.
NMR (CDCl3) 1.05 (m, 6H), 1.7 (m, 6H), 2.0 (m, 2H), 2.5 (m, 2H), 2.8 (m, 2H), 2.85 (m, 2H), 3.3 (m, 2H), 4.0 (m, 2H)
TG 103.2 (3 μmol) 97.9 (10 μmol) 65.3 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
3-acetyl-2,5-dichlorothiophene (195 mg), benzylisopropylamine (149 mg), and paraformaldehyde (40 mg) were reacted in dioxane (0.2 ml) at 130° C. for 2 hours.
NMR (CDCl3) 1.0-1.2 (m, 6H), 2.0 (m, H), 2.6 (m, 2H), 2.8-2.9 (m, 2H), 3.4-3.8 (m, 2H), 7-7.5 (m, 6H)
TG 17.8 (3 μmol) 10.5 (10 μmol) −1.1 (30 μmol)
SOCE 0 (10 μmol) 20 (30 μmol) 50 (100 μmol)
IICR 50 (10 μmol) 80 (30 μmol) 100 (100 μmol)
3-acetyl-2,5-dichlorothiophene (195 mg), 2-hydroxyethylisopropylamine (103 mg), and paraformaldehyde (40 mg) were reacted in dioxane (0.2 ml) at 130° C. for 2 hours.
NMR (CDCl3) 11.9-1.1 (m, 6H), 2.3 (m, 2H), 2.7 (m, 2H), 3.6 (m, 2H), 3.8 (m, 2H), 7.2 (s, 1H)
TG 35 (3 μmol) 13 (10 μmol) 2.5 (30 μmol)
SOCE 50 (10 μmol) 20 (30 μmol) 10 (100 μmol)
IICR 40 (10 μmol) 90 (30 μmol) 100 (100 μmol)
3-acetyl-2,5-dichlorothiophene (195 mg), benzyl-2-hydroxyethyl amine (151 mg), and paraformaldehyde (40 mg) were reacted in dioxane (0.2 ml) at 130° C. for 2 hours.
NMR (CDCl3) 2.5 (m, 2H), 2.9 (m, 2H), 3.6-3.7 (m, 4H), 4.2 (m, 2H), 7.0-7.5 (m, 6H)
TG 49.1 (3 μmol) 17.6 (10 μmol) 7.7 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 50 (100 μmol)
IICR 0 (10 μmol) 40 (30 μmol) 70 (100 μmol)
2-acetyl naphthalene (170 mg), 2-hydroxyethylisopropylamine (103 mg), and paraformaldehyde (40 mg) were reacted in dioxane (0.2 ml) at 130° C. for 2 hours reaction.
NMR (CDCl3) 1.05 (m, 6H), 2.7 (m, 2H), 2.9 (m, 1H), 3.7 (m, 2H), 3.85 (m, 2H), 4.3 (m, 2H), 7.6-8.4 (m, 7H)
TG 82.5 (3 μmol) 62.4 (10 μmol) 28.3 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
Chloroacetophenone (154 mg), 2-hydroxyethylisopropylamine (103 mg), and diisopropylethyl amine (128 mg) were reacted in dioxane (0.2 ml) at 130° C. for 2 hours.
NMR (CDCl3) 1.05 (m, 6H), 3.1 (m, 2H), 3.6 (m, 1H), 3.6 (m, 2H), 4.0 (m, 2H), 7.1-7.2 (m, 5H)
TG 67.6 (3 μmol) 63.6 (10 μmol) 27.4 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 40 (100 μmol)
4-chlorobutyrophenone (269 mg), 2-hydroxyethylisopropylamine (152 mg), and diisopropylethyl amine (187 mg) were reacted at 120° C. for 2 hours.
NMR (CDCl3) 1.4 (m, 6H), 2.5 (m, 2H), 3.05 (m, 4H), 3.0 (m, 2H), 3.6 (m, 2H), 6.6 (1H), 6.5 (1H), 7.1-7.2.0 (7H)
TG 95.2 (3 μmol) 92.5 (10 μmol) 82.9 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 30 (100 μmol)
IICR 20 (10 μmol) 20 (30 μmol) 20 (100 μmol)
2-acetylpyrazine (122 mg), methylhydroxyethyl amine (75 mg), and paraformaldehyde (40 mg) were reacted at 130° C. for 2 hours.
NMR (CDCl3) 1.8-2.8 (m, 7H), 3.0 (m, 2H), 3.2 (m, 2H), 7.5-8.1 (3H)
TG 99.0 (3 μmol) 53.6 (10 μmol) 11.0 (30 μmol)
SOCE 0 (10 μmol 10 (30 μmol) 20 (100 μmol)
IICR 20 (10 μmol) 30 (30 μmol) 30 (100 μmol)
Acetylpyridine (121 mg), benzylethyl amine (135 mg), and paraformaldehyde (40 mg) were reacted in dioxane (0.2 ml) at 130° C. for 2 hours.
NMR (CDCl3) 1.05 (m, 3H), 1.8 (m, 2H), 1.9 (m, 2H), 2.6 (m, 2H), 3.5 (m, 2H), 7.-8.5 (91-1)
TG 100 (3 μmol) 85.9 (10 μmol) 46.0 (30 μmol)
SOCE 0 (10 μmol) 20 (30 μmol) 60 (100 μmol)
IICR 20 (10 μmol) 20 (30 μmol) 50 (100 μmol)
4-acetylpyridine (121 mg), benzyl-t-butyl amine (149 mg), and paraformaldehyde (40 mg) were reacted in dioxane (0.2 ml) at 130° C. for 2 hours.
NMR (CDCl3) 1.05 (m, 9H), 2.5 (m, 2H), 3.4 (m, 2H), 3.8 (m, 2H), 7.5 (5H), 7.9 (2H), 8.3 (2H)
TG 102 (3 μmol) 96 (10 μmol) 69 (30 μmol)
SOCE 0 (10 μmol) 10 (30 μmol) 30 (100 μmol)
IICR 0 (10 μmol) 20 (30 μmol 0 (100 μmol)
4-fluoroacetophenone (138 mg), acetyl piperazine (180 mg), and paraformaldehyde (40 mg) were reacted in dioxane (0.2 ml) at 130° C. for 2 hours.
NMR (CDCl3) 2.5 (m, 2H), 3.0 (m, 4H), 3.0 (m, 2H), 3.6 (m, 2H), 6.5 (2H), 6.5 (1H), 7.1-7.2 (4H), 8.0 (m, 2H)
TG 100 (3 μmol 91.0 (10 μmol) 49.7 (30 μmol)
SOCE 0 (10 μmol) 10 (30 μmol) 30 (100 μmol)
IICR 30 (10 μmol) 20 (30 μmol) 20 (100 μmol)
4-fluoroacetophenone (138 mg), benzylisopropylamine (149 mg), and paraformaldehyde (40 mg) were reacted in dioxane (0.2 ml) at 130° C. for 2 hours.
NMR (CDCl3) 1.05 (m, 6H), 2.5 (m, 4H), 2.9 (m, 1H), 3.9 (m, 2H), 7.0-7.5 (7H), 8.0 (2H)
TG 104 (3 μmol) 82 (10 μmol) 37 (30 μmol)
SOCE 0 (10 μmol) 30 (30 μmol) 50 (100 μmol)
IICR 20 (10 μmol) 80 (30 μmol) 30 (100 μmol)
2-acetylpyrazine (122 mg), t-butylbenzylamine (162 mg), and paraformaldehyde (40 mg) were reacted in dioxane (0.2 ml) at 130° C. for 2 hours.
NMR (CDCl3) 1.2 (m, 6H), 2.7 (m, 2H), 3.1 (m, 2H), 3.7 (m, 2H), 7.0 (m, 1H), 7.3 (m, 5H), 8.5 (m, 1H), 9.1 (m, 1H)
TG 10.1 (3 μmol) 2.7 (10 μmol) 0.4 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 10 (100 μmol)
IICR 20 (10 μmol) 80 (30 μmol) 90 (100 μmol)
2-acetylpyrazine (122 mg), t-butyl-2-hydroxyethyl amine (117 mg), and paraformaldehyde (40 mg) were reacted in dioxane (0.2 ml) at 130° C. for 2 hours.
NMR (CDCl3) 1.10 (s, 9H), 2.60 (m, 2H), 2.45 (m, 2H), 3.9 (m, 2H), 4.25 (m, 2H), 8.71 (s, 1H), 8.8 (s, 1H), 9.21 (s, 1H)
TG 45.8 (3 μmol) 7.1 (30 μmol)
SOCE 10 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 0 (100 wimp
2-acetylpyrazine (122 mg), methylbenzylamine (121 mg), and paraformaldehyde (40 mg) were reacted in dioxane (0.2 ml) at 130° C. for 2 hours.
NMR (CDCl3) 2.15 (m, 2H), 3.0 (m, 2H), 3.4 (m, 2H), 3.7 (m, 3H),
TG 24.5 (3 μmol) −1.3 (10 μmol) −3.1 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 50 (100 μmol)
2-acetylpyridine (121 mg), spermidine (87 mg), and paraformaldehyde (40 mg) were reacted in dioxane (0.2 ml) at 130° C. for 2 hours.
NMR (CDCl3) 1.7-2.4 (6H), 2.6 (m, 4H), 3.4-3.6 (m, 8H), 3.8 (2H), 7.4-8.4 (8H)
TG 106.8 (3 μmol) 87.0 (10 μmol) 45.3 (30 μmol)
SOCE 0 (10 μmol) 10 (30 μmol) 10 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 30 (100 μmol
2-acetylpyridine (121 mg), piperidine methanol (115 mg), and paraformaldehyde (40 mg) were reacted in dioxane (0.2 ml) at 130° C. for 2 hours.
NMR (CDCl3) 1.2-2.2 (6H), 2.6 (m, 4H), 3.4-4.0 (m, 6H), 7.4-8.2 (4H)
TG 107 (3 μmol) 93.5 (10 μmol) 81.2 (30 μmol
SOCE 10 (10 μmol) 0 (30 μmol) 20 (100 μmol
IICR 0 (10 μmol) 20 (30 μmol) 50 (100 μmol
2-acetylfluorene (208 mg), ethylbenzylamine (135 mg), and paraformaldehyde (40 mg) were reacted in dioxane (0.2 ml) at 130° C. for 2 hours.
NMR (CDCl3) 1.0 (m, 3H), 2.2 (m, m, 2H), 2.5 (m, 2H), 2.8 (m, m, 2H), 2.9 (m, 2H), 7.1-8.1 (m, 7H)
TG 100 (3 μmol) 73.6 (10 μmol) 28.5 (30 μmol)
SOCE 20 (10 μmol) 60 (30 μmol) 70 (100 μmol)
IICR 10 (10 μmol) 40 (30 μmol) 70 (100 μmol)
5-acetyl-2,4-dimethylthiazole (155 mg), isopropylbenzylamine (162 mg), and paraformaldehyde (40 mg) were reacted in dioxane (0.2 ml) at 130° C. for 2 hours.
NMR (CDCl3) 1.0-1.2 (m, 12H), 2.55 (m, 2H), 2.6-2.7 (m, 6H), 2.8 (m, m, 2H), 3.6 (m, 2H)
TG 36 (3 μmol) −2.5 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 20 (10 μmol) 90 (30 μmol) 100 (100 μmol)
5-acetyl-2,4-dimethylthiazole (155 mg), hydroxyethylethyl amine (104 mg), and paraformaldehyde (40 mg) were reacted in dioxane (0.2 ml) at 130° C. for 2 hours.
NMR (CDCl3) 2.55 (m, 2H), 2.65 (m, 10H), 3.5-3.7 (m, 4H), 5. (m, 4H)
TG 103 (3 μmol) 70 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 0 (10 μmol) 40 (30 μmol) 40 (100 μmol)
3-acetyl-2,5-dimethylfuran (155 mg), isopropylbenzylamine (49 mg), and paraformaldehyde (40 mg) were reacted in dioxane (0.2 ml) at 130° C. for 2 hours.
NMR (CDCl3) 1.05 (m, 6H), 1.25 (m, 6H), 2.2 (m, 2H), 2.4 (m, 2H), 3.6 (m, 2H), 3.8 (m 1H), 7.2 (m, 6H)
TG 98 (3 μmol) 44.5 (30 μmol)
SOCE 0 (10 μmol) 0 (30 primp 0 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
3-acetylthiophene (126 mg), N-isopropylbenzylamine (149 mg), and paraformaldehyde (36 mg) were reacted in dioxane (0.2 ml) at 130° C. for 2 hours.
NMR (CDCl3) 1.05 (m, 6H), 2.5 (m, 2H), 3.0 (m, 2H), 3.0 (m, 1H), 3.7 (m, 2H), 7.0-7.5 (6H), 7.6 (2H)
TG 65.3 (3 μmol) 10.8 (10 μmol) −24.2 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 10 (100 μmol)
IICR 0 (10 μmol) 30 (30 μmol) 80 (100 μmol)
3-acetylthiophene (126 mg), phenylethyl amine (121 mg), and paraformaldehyde (40 mg) were reacted in dioxane (0.2 ml) at 130° C. for 2 hours.
NMR (CDCl3) 2.5 (m, 2H), 2.7 (m, 2H), 3.4 (m, 2H), 3.8 (m, 2H), 7.1-7.2. (5H), 7.5 (m, 2H), 8.0 (m, 2H)
TG 113.3 (3 μmol) 108.7 (10 μmol) 104.4 (30 μmol)
SOCE 0 (10 μmol) 10 (30 μmol) 20 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
3-acetylimidazole (70 mg), benzylisopropylamine (140 mg), and paraformaldehyde (40 mg) were reacted in dioxane (0.2 ml) at 130° C. for 2 hours.
NMR (CDCl3) 1.05 (m, 6H), 2.5 (m, 2H), 3.0 (m, 2H), 3.0 (m, 1H), 3.7 (m, 2H), 5.9 (1H), 6.8-7.4 (6H), 8.0 (1H)
TG 112 (3 μmol) 122 (10 μmol) 144.9 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 20 (100 μmol)
IICR 20 (10 μmol) 20 (30 μmol) 0 (100 μmol)
3-acetyl-2,3-dimethylfuran (136 mg), benzylisopropylamine (149 mg), and paraformaldehyde (40 mg) were reacted in dioxane (0.2 ml) at 130° C. for 2 hours.
NMR (CDCl3) 1.0 (m, 6H), 1.9 (m, 3H), 2.3 (m, 3H), 2.4 (m, 2H), 2.8 (m, 2H), 3.6 (m, 2H), 7.0 (m, 6H)
TG 34.8 (3 μmol) 6.0 (10 μmol) −13.9 (30 μmol)
SOCE 10 (10 μmol) 30 (30 μmol) 70 (100 μmol)
IICR 20 (10 μmol) 30 (30 μmol) 90 (100 μmol)
3-acetyl-2,3-dimethylfuran (136 mg), 2-ethylaminoethanol (89 mg), and paraformaldehyde (40 mg) were reacted in dioxane (0.2 ml) at 130° C. for 2 hours.
NMR (CDCl3) 1.0 (m, 3H), 2.0 (m, 6H), 2.2 (m, 4H), 2.6 (m, 4H), 2.6 (m, 2H), 7.0 (s, 1H)
TG 61.7 (3 μmol) 11.4 (10 μmol) −5.9 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol
IICR 0 (10 μmol) 0 (30 μmol) 50 (100 μmol)
3-acetyl-2,3-dimethylfuran (136 mg), benzylaminoethanol (151 mg), and paraformaldehyde (40 mg) were reacted in dioxane (0.2 ml) at 130° C. for 2 hours.
NMR (CDCl3) 2.0 (m, 3H), 2.15 (m, 2H), 2.5 (m, 2H), 2.8 (m, 2H), 4.1 (m, 2H), 7.1 (m, 6H)
TG 76.6 (3 μmol) 43.8 (10 μmol 2.5 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 20 (10 μmol) 0 (30 μmol) 20 (100 μmol)
3-acetyl-2,3-dimethylthiophene (154 mg), ethylethanol amine (89 mg), and paraformaldehyde (40 mg) were reacted in dioxane (0.2 ml) at 130° C. for 2 hours.
NMR (CDCl3) 1.0 (m, 3H), 2.4 (m, 8H), 2.6 (m, 4H), 2.9 (m, 2H), 6.9 (s, 1H)
TG 96.3 (3 μmol) 75.1 (10 μmol) 30.9 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 20 (100 μmol)
IICR 20 (10 μmol) 0 (30 μmol) 20 (100 μmol)
3-acetyl-2,3-dimethylthiophene (154 mg), diethanol amine (105 mg), and paraformaldehyde (40 mg) were reacted in dioxane (0.2 ml) at 130° C. for 2 hours.
NMR (CDCl3) 2.4 (m, 3H), 2.5 (m, 3H), 2.6 (m, 2H), 2.7 (m, 2H), 2.9 (m, 2H), 3.0 (m, 2H), 3.7 (m, 2H), 3.7 (m, 2H), 4.3 (m, 2H), 7.0 (s, 1H)
TG 107 (3 μmol) 107 (10 μmol) 77 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
3-acetyl-2,3-dimethylthiophene (154 mg), isopropylethanol amine (103 mg), and paraformaldehyde (40 mg) were reacted in dioxane (0.2 ml) at 130° C. for 2 hours.
NMR (CDCl3) 1.0 (m, 6H), 2.15 (m, 6H), 2.2 (m, 2H), 2.8 (m, 2H), 3.8 (m, 2H), 4.1 (m, 2H), 7.0 (s, 1H)
TG 102 (3 μmol) 99 (10 μmol) 87.1 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 20 (100 μmol)
3-acetylpyridine (242 mg), t-butylbenzylamine (326 mg), and paraformaldehyde (80 mg) were reacted in dioxane (0.4 ml) at 130° C. for 2 hours.
NMR (CDCl3) 1.17 (s, 9H), 2.64 (m, 2H), 3.02 (m, 2H), 3.72 (m, 2H), 7.2-9.1 (m, 9H)
TG 4.8 (3 μmol) 1.0 (10 μmol) 0.5 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 20 (10 μmol) 90 (30 μmol) 100 (100 μmol)
3-acetylpyridine (280 mg), t-butylethanol amine (272 mg), and paraformaldehyde (80 mg) were reacted in dioxane (0.4 ml) at 130° C. for 2 hours.
NMR (CDCl3) 1.13 (s, 9H), 2.66 (m, 2H), 2.90 (m, 2H), 3.83 (m, 2H), 4.39 (m, 2H), 7.45, 8.26, 8.80, 9.17
TG 85.5 (3 μmol) 49.0 (10 μmol) 7.5 (30 μmol)
SOCE 0 (10 μmol 0 (30 μmol) 0 (100 μmol)
IICR 0 (10 μmol 10 (30 μmol) 10 (100 μmol
2-acetylfuran (220 mg), benzylmethyl amine (242 mg), and paraformaldehyde (40 mg) were reacted at 130° C. for 2 hours.
NMR (CDCl3) 2.16 (m, 3H), 2.49 (m, 2H), 2.89 (m, 2H), 3.55 (m, 2H), 6.5-7.7 (m, 8H)
TG 96.3 (3 μmol 75.1 (10 μmol 30.9 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 10 (100 μmol)
IICR 30 (10 μmol) 70 (30 μmol) 80 (100 μmol)
2-acetylfuran (220 mg), butylethanol amine (134 mg), and paraformaldehyde (78 mg) were reacted at 130° C. for 2 hours.
NMR (CDCl3) 0.90 (m, 3H), 1.3 (m, 4H), 2.5 (m, 2H) 2.90 (m, 2H), 3.54 (m, 2H), 3.76 (2H), 6.53 (s, 1H), 7.21 (1H), 7.6 (1H)
TG 25.0 (3 μmol) 2.9 (10 μmol) −2.5 (30 μmol
SOCE 0 (10 μmol) 0 (30 μmol) 10 (100 μmol)
IICR 0 (10 μmol) 70 (30 μmol) 80 (100 μmol)
2-acetylfuran (220 mg), methylethanol amine (155 mg), and paraformaldehyde (78 mg) were reacted at 130° C. for 2 hours.
NMR (CDCl3) 2.2-2.5 (m, 7H), 3.6-3.9 (m, 4H), 6.56, 7.21, 7.61
TG 16.5 (3 μmol) 2.8 (10 μmol) 0.5 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 0 (10 μmol) 90 (30 μmol) 80 (100 μmol)
3-acetylthiophene (252 mg), methylbenzylamine (244 mg), and paraformaldehyde (78 mg) were reacted at 130° C. for 2 hours.
NMR (CDCl3) 2.16 (m, 3H), 2.23 (m, 2H), 3.04 (m, 2H), 3.63 (m, 2H), 7.1-8.0 (m, 8H)
TG 102 (3 μmol) 79.0 (10 μmol 37.3 (30 μmol
SOCE 0 (10 μmol) 0 (30 μmol) 20 (100 μmol)
IICR 10 (10 μmol) 10 (30 μmol 80 (100 μmol)
3-acetylthiophene (252 mg), butylethanol amine (234 mg), and paraformaldehyde (78 mg) were reacted at 130° C. for 2 hours.
NMR (CDCl3) 0.90 (m, 3H), 1.4 (m, 4H), 2.56 (m, 2H), 2.95 (m, 2H), 3.78 (m, 2H), 7.5-8.1 (m, 3H)
TG 83.6 (3 μmol) 57.6 (10 μmol) 15.2 (30 μmol)
SOCE 0 (10 μmol 0 (30 μmol) 0 (100 μmol)
IICR 20 (10 μmol 10 (30 μmol 70 (100 μmol)
2-acetylthiophene (252 mg), benzyl-t-butyl amine (234 mg), and paraformaldehyde (78 mg) were reacted at 130° C. for 2 hours.
NMR (CDCl3) 1.12 (m, 9H), 2.34 (m, 2H), 2.94 (m, 2H), 3.84 (m, 2H), 7.5-8.0 (m, 8H)
TG 83.7 (3 μmol 55.3 (10 μmol) 11.8 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol 0 (100 μmol
IICR 10 (10 μmol 0 (30 μmol) 0 (100 μmol)
2-acetyl-5-methylfuran (248 mg), ethylbenzylamine (270 mg), and paraformaldehyde (78 mg) were reacted at 130° C. for 2 hours.
NMR (CDCl3) 1.09 ((m, 3H), 2.40 (m, 2H), 2.91 (m, 2H), 3.50 (m, 2H), 3.60 (m, 2H), 6.10 (m, 1H), 7.20 (m, 6H)
TG 51.7 (3 μmol) 2.2 (10 μmol) 4.3 (30 μmol)
SOCE 0 (10 μmol 0 (30 μmol 10 (100 μmol)
IICR 0 (10 μmol) 50 (30 μmol) 80 (100 μmol)
2-acetyl-5-methylfuran (248 mg), t-butylethanol amine (234 mg), and paraformaldehyde (78 mg) were reacted at 130° C. for 2 hours.
NMR (CDCl3) 2.24 (m, 3H), 2.48 (m, 3H), 2.85 (m, 2H), 3.55 (m, 2H), 6.1 (s, 1H), 7.0-7.4 (m, 7H)
TG 4.5 (3 μmol) 1.1 (10 μmol) 0 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 10 (10 μmol) 30 (30 μmol) 50 (100 μmol)
2-acetyl-5-methylfuran (248 mg), benzylmethyl amine (242 mg), and paraformaldehyde (78 mg) were reacted at 130° C. for 2 hours.
NMR (CDCl3) 2.24 (m, 3H), 2.48 (m, 3H), 2.85 (m, 2H), 3.55 (m, 2H), 6.1 (s, 1H), 7.0-7.4 (m, 6H)
TG 55.9 (3 μmol) 22.6 (10 μmol) 3.6 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 10 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol 70 (100 μmol)
2-acetylpyridine (242 mg), ethylbenzylamine (270 mg), and paraformaldehyde (78 mg) were reacted at 130° C. for 2 hours.
NMR (CDCl3) 0.88 (m, 3H), 2.41 (m, 2H), 2.61 (m, 2H), 2.93 (m, 2H), 3.48 (m, 2H), 3.69 (m, 2H), 7.1-8.3 (m, 9H)
TG 43.2 (3 μmol) 8.1 (10 μmol) 3.0 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 30 (10 μmol) 80 (30 μmol) 90 (100 μmol)
2-acetylpyridine (242 mg), diethanol amine (210 mg), and paraformaldehyde (78 mg) were reacted at 130° C. for 2 hours.
NMR (CDCl3) 2.74 (m, 2H), 3.06 (m, 2H), 3.65 (m, 2H), 3.78 (m, 4H), 4.32 (m, 2H), 7.7, 7.9, 8.1, 8.6
TG 42.6 (10 μmol) 10.1 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 50 (100 μmol)
2-acetylpyridine (242 mg), t-butylethanol amine (234 mg), and paraformaldehyde (78 mg) were reacted at 130° C. for 2 hours.
NMR (CDCl3) 1.12 (ms, 9H), 2.70 (m, 2H), 2.95 (m, 2H), 3.84 (m, 2H), 4.18 (m, 2H), 7.48, 7.85, 9.03, 8.69
TG 96.3 (3 μmol) 75.1 (10 μmol) 30.9 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
2-acetylthiophene (252 mg), benzylethanol amine (302 mg), and paraformaldehyde (78 mg) were reacted at 130° C. for 2 hours.
NMR (CDCl3) 2.64 (m, 2H), 2.95 (m, 2H), 3.7-3.8 (m, 4H), 4.3 (m, 2H), 7.0-7.7 (m, 7H)
TG 100.2 (3 μmol) 69.4 (10 μmol) 24.3 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
2-acetylthiophene (252 mg), t-butylethanol amine (234 mg), and paraformaldehyde (78 mg) were reacted at 130° C. for 2 hours.
NMR (CDCl3) 1.1 (s, 9H), 2.2 (m, 4H), 2.95 (m, 2H), 3.85 (m, 2H), 7.2, 7.8, 7.85
TG 64.7 (3 μmol 31.3 (10 μmol) 5.8 (30 μmol)
SOCE 0 (10 μmol 0 (30 μmol) 0 (100 μmol)
IICR 10 (10 μmol) 0 (30 μmol 0 (100 μmol)
2-acetylthiophene (252 mg), butylethanol amine (234 mg), and paraformaldehyde (78 mg) were reacted at 130° C. for 2 hours.
NMR (CDCl3) 0.9 (m, 3H), 1.4 (m, 4H), 2.2 (m, 2H), 2.35 (m, 2H), 3.8 (m, 2H), 7.2, 7.8, 7.9
TG 89.5 (3 μmol) 76.5 (10 μmol) 36.6 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 10 (10 μmol) 0 (30 μmol) 0 (100 μmol)
2-acetylpyridine (242 mg), benzylmethyl amine (242 mg), and paraformaldehyde (78 mg) were reacted at 130° C. for 2 hours.
NMR (CDCl3) 2.2 (m, 3H), 2.2 (m, 2H), 2.6 (m, 2H), 3.6 (m, 2H), 7.7 (m, 2H), 8.5 (m, 2H)
TG 55.7 (3 μmol) 23.8 (10 μmol) 6.0 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 0 (10 μmol) 10 (30 μmol) 80 (100 μmol)
4-acetylpyridine (242 mg), diethanol amine (210 mg), and paraformaldehyde (78 mg) were reacted at 130° C. for 2 hours.
NMR (CDCl3) 1.9 (m, 2H), 2.1 (m, 2H), 2.6 (m, 2H), 2.7 (m, 2H), 3.5-3.7 (m, 4H), 7.0-9.2 (m, m, 4H)
TG 56.2 (3 μmol) 13.6 (10 μmol) 12 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 20 (100 μmol)
IICR 0 (10 μmol) 60 (30 μmol) 80 (100 μmol)
4-acetylpyridine (242 mg), butylethanol amine (234 mg), and paraformaldehyde (78 mg) were reacted at 130° C. for 2 hours.
NMR (CDCl3) 0.9 (m, 3H), 1.4-1.4 (m, 4H), 2.5 (m, 2H), 2.6 (m, 2H), 2.9 (m, 2H), 3.7 (m, 2H), 4.1 (m, 2H), 7.5, 7.8, 8.1, 8.7
TG 97.3 (3 μmol) 63.2 (10 μmol) 27.0 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 0 (10 μmol) 10 (30 μmol) 20 (100 μmol)
2-acetylpyridine (242 mg), methylethanol amine (150 mg), and paraformaldehyde (78 mg) were reacted at 130° C. for 2 hours.
NMR (CDCl3) 2.35 (m, 2H), 2.7 (m, 3H), 2.9 (m, 2H), 3.7 (m, 2H), 7.5, 7.8, 8.1, 8.4
TG 81.4 (3 μmol 80.8 (10 μmol) 53.1 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
2-acetyl-3-ethylpyrazine (150 mg), isopropylethanol amine (103 mg), and paraformaldehyde (38 mg) were reacted at 130° C. for 2 hours.
NMR (CDCl3) 1.30 (m, 6H), 2.73 (m, 2H), 3.14 (m, 2H), 3.9 (m, 2H), 4.25 (m, 2H), 8.4, 8.5
TG 75.4 (3 vitriol) 42.9 (10 μmol) 17.7 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol
IICR 0 (10 vitriol) 0 (30 μmol) 80 (100 μmol)
2-acetylthiophene (240 mg), ethylbenzylamine (270 mg), and paraformaldehyde (78 mg) were reacted at 130° C. for 2 hours.
NMR (CDCl3) 1.0 (m, 3H), 2.5 (m, 2H), 3.0 (m, 2H), 3.6 (m, 4H), 7.0-7.8 (m, 8H)
TG 39.1 (3 μmol) 3.3 (10 μmol) 0.4 (30 μmol)
SOCE 0 (10 μmol) 10 (30 μmol) 40 (100 μmol)
IICR 20 (10 μmol) 0 (30 μmol) 20 (100 μmol)
3-acetylthiophene (252 mg), methylethanol amine (150 mg), and paraformaldehyde (78 mg) at 130° C. for 2 hours.
NMR (CDCl3) 2.15 (m, 2H), 2.2 (m, 5H), 2.8 (m, 2H), 3.7 (m, 2H), 6.7 (1H), 6.6 (1H), 8.0 (1H)
TG 85.3 (3 μmol) 64.3 (10 μmol) 19.0 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 0 (10 μmol) 30 (30 μmol) 40 (100 μmol)
2-acetyl-5-methylfuran (248 mg), butylethanol amine (234 mg), and paraformaldehyde (78 mg) were reacted at 130° C. for 2 hours.
NMR (CDCl3) 1.90 (m, 3H), 1.40 (m, 4H), 2.4-2.8 (m 4H), 3.3 (m, 2H), 3.7 (m, 2H), 6.15, 7.15
TG 11.6 (3 μmol) −6.1 (10 μmol) −7.9 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 0 (10 μmol) 30 (30 μmol) 50 (100 μmol)
2-acetyl thiazole (32 mg), t-butylbenzylamine (34 mg), and paraformaldehyde (10 mg) were reacted at 130° C. for 2 hours.
NMR (CDCl3) 1.00 (s, 9H), 2.70 (m, 2H), 2.95 (m, 2H), 3.7 (m, 2H), 7.0-7.7 (m, 8H)
TG 19.1 (3 μmol) 5.8 (10 μmol) −0.3 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 10 (100 μmol)
IICR 50 (10 μmol) 90 (30 μmol) 80 (100 μmol)
5-acetyl-2,4-dimethylthiazole (82.5 mg), isopropylethanol amine (55 mg), and paraformaldehyde (78 mg) were reacted at 130° C. for 2 hours.
NMR (CDCl3) 1.00 (m, s, 6H), 2.9 (m, 2H), 2.6 (m, 3H), 2.8 (m, 2H), 2.97 (m, 1H), 3.8 (m, 2H)
TG 101 (3 μmol) 91.4 (10 μmol) 60.6 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 0 (10 μmol 0 (30 μmol) 20 (100 μmol)
2-acetyl thiazole (33 mg), benzylmethyl amine (32 mg), and paraformaldehyde (10 mg) were reacted at 130° C. for 2 hours.
NMR (CDCl3) 2.2 (m, 3H), 2.4 (m, 2H), 2.5 (m, 2H), 3.6-3.7 (m, 2H), 7.0, 8.0 (m, 8H)
TG 48.5 (3 μmol) 19.6 (10 μmol) 0.4 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 20 (10 μmol) 0 (30 μmol) 20 (100 μmol)
2-acetylpyridine (248 mg), methylethanol amine (150 mg), and paraformaldehyde (78 mg) were reacted at 130° C. for 2 hours.
NMR (CDCl3) 1.50 (m, 2H), 1.75 (m, 2H), 2.80 (m, 2H), 3.4 (m, 2H), 6.9 (m, 2H), 7.9 (m, 2H)
TG 53.7 (3 μmol) 19.9 (10 μmol) 3.4 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 20 (100 μmol)
2-acetyl-3-ethylpyrazine (148 mg), diethanol amine (119 mg), and paraformaldehyde (40 mg) were reacted at 130° C. for 2 hours.
NMR (CDCl3) 1.31 (t, 3H), 2.75 (m, 43H), 3.25 (m, 2H), 3.71 (m, 2H), 3.80 (M, 2H), 4.0 (m, 2H), 8.2 (s, 1H), 8.25 (s, 1H)
TG 76.3 (3 μmol) 45.2 (10 μmol) 10.2 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 20 (10 μmol) 0 (30 μmol) 20 (100 μmol)
Acetylthiophene (126 mg), diethanol amine (105 mg), and paraformaldehyde (40 mg) were reacted at 130° C. for 2 hours.
NMR (CDCl3) 2.5 (m, 2H), 2.6 (m, 2H), 2.8 (m, 2H), 3.6 (m, 4H), 4.2 (m, 2H), 6.6, 7.7, 8.0
TG 87 (3 μmol) 22 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol 0 (100 μmol)
IICR 10 (10 μmol) 20 (30 μmol) 20 (100 μmol)
4-acetylpyridine (242 mg), methylethanol amine (150 mg), and paraformaldehyde (78 mg) were reacted at 130° C. for 2 hours.
NMR (CDCl3) 2.69 (m, 2H), 2.89 (m, 2H), 3.69 (m, 3H), 7.8 (m, 2H), 8.7 (m, 2H)
TG 75 (3 μmol) 8.6 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 70 (100 μmol)
2-acetyl-4-methylthiazole (152 mg), isopropylbenzylamine (134 mg), and paraformaldehyde (78 mg) were reacted at 130° C. for 2 hours.
NMR (CDCl3) 0.9-1.1 (m, 6H), 2.3-2.9 (m, 3H), 3.4-3.8 (m, 4H), 7.0-7.4 (m, 6H)
TG 26 (3 μmol) 8.6 (30 μmol) 5.6 (10 μmol) 0.2 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol 30 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 70 (100 μmol)
2-acetyl-4-methylthiazole, n-butyl-2-hydroxyethyl amine, and paraformaldehyde were reacted at 130° C. for 2 hours.
NMR (CDCl3) 0.6-0.95 (m, 3H), 1.1-1.5 (m, 4H), 2.5-2.6 (m, 6H), 2.9 (m, 2H), 3.5-3.8 (m, 4H), 7.25 (s, 1H)
TG 40 (3 μmol) 9.9 (10 μmol) 2.6 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 10 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 70 (100 μmol)
2-acetyl-4-methylthiazole, methylbenzylamine, and paraformaldehyde were reacted at 130° C. for 2 hours.
NMR (CDCl3) 2.1-3.6 (m, 5H), 2.4-3.1 (m, 2H), 3.4-3.7 (m, 2H), 7.0-7.2 (m, 6H)
TG 33 (3 μmol) 7.1 (10 μmol) (130 μmol)
SOCE 10 (10 μmol) 10 (30 μmol) 10 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 70 (100 μmol)
2-acetyl-5-chlorothiophene (320 mg), isopropylbenzylamine (298 mg), and paraformaldehyde (78 mg) were reacted at 130° C. for 2 hours.
NMR (CDCl3) 0.9-1.2 (m, 6H), 2.50 (m, 2H), 2.7-3.0 (m, 3H), 3.5-3.7 (m, 2H), 6.8-7.2 (m, 7H)
TG 2.6 (3 μmol) 4.7 (10 μmol) −4.7 (30 μmol)
SOCE 0 (10 μmol) 20 (30 μmol) 40 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 70 (100 μmol)
2-acetyl-5-chlorothiophene, 2-hydroxyethylisopropylamine, and paraformaldehyde were reacted at 130° C. for 2 hours.
NMR (CDCl3) 2.69 (m, 2H), 2.89 (m, 2H), 3.69 (m, 3H), 7.8 (m, 2H), 8.7 (m, 2H)
TG 58 (3 μmol) 27 (10 μmol) 7.9 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 70 (100 μmol)
2-acetyl-5-chlorothiophene, 2-hydroxyethylbenzylamine, and paraformaldehyde were reacted at 130° C. for 2 hours.
NMR (CDCl3) 2.69 (m, 2H), 2.89 (m, 2H), 3.69 (m, 3H), 7.8 (m, 2H), 8.7 (m, 2H)
TG 32 (3 μmol) 28 (10 μmol) 6.3 (30 μmol)
SOCE 10 (10 μmol) 0 (30 μmol) 10 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 70 (100 μmol)
2-acetyl-5-bromothiophene (410 mg), t-butylbenzylamine (326.5 mg), and paraformaldehyde (78 mg) were heated in dioxane (0.4 ml) at 130° C. for 30 minutes.
NMR (CDCl3) 1.20 (s, 9H), 2.64 (t, 2H), 2.97 (t, 2H), 3.73 (m, 2H), 7.1 (s, 1H), 7.4-7.6 (m, 6H)
TG 15 (0.3 μmol) 12 (1 μmol) 4.7 (3 μmol) 4.5 (10 μmol) 3.1 (30 μmol)
NMR (CDCl3) 1.88 (m, 2H), 2.75 (m, 2H), 3.78 (m, 4H), 4.37 (m, 2H), 8.78 (m, 2H), 9.21 (1H)
TG 106 (3 μmol) 71.7 (30 μmol)
SOCE 10 (30 μmol) 30 (100 μmol)
IICR 20 (10 μmol) 0 (30 μmol) 10 (100 μmol)
NMR (CDCl3) 2.64 (m, 2H), 3.42 (m, 2H), 3.86 (m, 2H), 7.28 (m, 5H), 8.24 (m, 1H), 8.79 (m, 1H), 9.17 (m, 1H)
TG 108 (3 μmol) 88.5 (30 μmol)
SOCE 0 (30 μmol) 10 (100 μmol)
IICR 10 (10 μmol) 0 (30 μmol) 40 (100 μmol)
NMR (CDCl3) 2.48 (m, 2H), 3.70 (m, 1H), 5.29 (m, 1H), 6.54 (m, 1H), 6.9-7.4 (m, 6H)
TG 95.7 (3 μmol) 40.0 (30 μmol)
SOCE 20 (30 μmol) 40 (100 μmol)
IICR 40 (10 μmol) 20 (30 μmol) 20 (100 μmol)
NMR (CDCl3) 2.75 (m, 2H), 2.85 (m, 2H), 3.60 (m, 2H), 3.70 (m, 2H), 5.31 (m, 2H), 8.17 (1H), 8.53 (s, 1H), 8.68 (s, 1H), 9.23 (s, 1H)
TG 90.6 (3 μmol) 25.6 (30 μmol)
SOCE 0 (30 μmol) 10 (100 μmol)
IICR 40 (10 μmol) 30 (30 μmol) 20 (100 μmol)
NMR (CDCl3) 2.64 (m, 2H), 3.35 (m, 2H), 3.7 (m, 2H), 4.37 (m, 2H), 7.24 (m, 5H), 7.73 (m, 2H), 8.82 (m, 2H).
TG 99.0 (3 μmol) 51.5 (30 μmol)
SOCE 0 (30 μmol) 0 (100 μmol)
IICR 20 (10 μmol) 20 (30 μmol) 80 (100 μmol)
NMR (CDCl3) 2.46 (m, 2H), 2.65 (m, 2H), 3.14 (m, 2H), 3.67 (m, 2H), 5.30 (s1H), 6.54 (1H), 7.14 (1H), 7.57 (1H)
TG 106 (3 μmol) 60.6 (30 μmol)
SOCE 0 (30 μmol) 0 (100 μmol)
IICR 30 (10 μmol) 30 (30 μmol) 30 (100 μmol)
2-acetylpyrazine (244 mg), tetramethylenediamine (88 mg), and paraformaldehyde (80 mg) were reacted at 130° C. for 2 hours.
NMR (CDCl3) 1.66 (m, 4H), 2.74 (m, 2H), 3.35 (m, 2H), 3.62 (m, 2H), 7.60 (m, 2H), 8.76 (s, 1H)
TG 102 (3 μmol) 45.2 (30 μmol)
SOCE 0 (30 μmol) 0 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 20 (100 μmol)
NMR (CDCl3) 2.52 (m, 2H), 2.72 (m, 2H), 3.00 (m, 2H), 3.73 (m, 2H), 4.38 (m, 4H), 6.91 (1H), 7.48 (1H)
TG 37.8 (3 μmol) 4.7 (10 μmol) 3.7 (30 μmol)
SOCE 0 (30 μmol) 0 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 20 (100 μmol)
NMR (CDCl3) 0.95 (m, 3H), 2.51 (m, 2H), 2.90 (m, 2H), 3.55 (m, 4H), 6.8-7.6 (m, 7H)
TG 7.4 (3 μmol) 4.0 (30 μmol)
SOCE 30 (30 μmol) 40 (100 μmol)
IICR 30 (10 μmol) 20 (30 μmol) 60 (100 μmol)
NMR (CDCl3) 2.23 (m, 2H), 2.51 (m, 2H), 2.85 (m, 2H), 3.55-3.6 (m, 3H) 6.95-7.5 (m, 7H)
TG 26.2 (3 μmol) 7.1 (30 μmol)
SOCE 30 (30 μmol) 40 (100 μmol)
IICR 20 (10 μmol) 0 (30 μmol) 40 (100 μmol)
NMR (CDCl3) 1.17 (s, 9H), 2.64 (m, 2H), 2.97 (m, 2H), 3.72 (m, 2H), 6.9-7.7 (m, 7H)
TG −3.1 (3 μmol) 3.5 (30 μmol)
SOCE 0 (30 μmol) 30 (100 μmol)
IICR 50 (10 μmol) 60 (30 μmol) 70 (100 μmol)
NMR (CDCl3) 1.24 (m, 3H), 2.55 (m, 1H), 2.74 (m, 2H), 3.70 (m, 2H), 8.79 (1H), 9.05 (1H), 9.22 (1H)
TG 101.0 (3 μmol) 80.0 (30 μmol)
SOCE 0 (30 μmol) 0 (100 μmol)
IICR 20 (10 μmol) 20 (30 μmol) 50 (100 μmol)
NMR (CDCl3) 1.77 (m, 4H), 2.11 (m, 2H), 2.73 (m, 2H), 3.37 (m, 2H), 3.46 (m, 2H), 3.70 (m, 2H), 8.6-8.7 (m, 2H), 8.24 (s, 1H)
TG 84.9 (3 μmol) 21.2 (30 μmol)
SOCE 0 (30 μmol) 0 (100 μmol)
IICR 0 (10 μmol) 20 (30 μmol) 50 (100 μmol)
2-acetylbenzothiophene (352 mg), isopropylbenzylamine (298 mg), and paraformaldehyde (76 mg) were reacted at 130° C. for 2 hours.
NMR (CDCl3) 1.05 (m, 9H), 2.65 (m, 2H), 2.95 (m, 1H), 3.54-3.6 (m, 2H), 7.15-7.66 (m, 10H)
TG 11.1 (3 μmol) 1.1 (30 μmol)
SOCE 0 (30 μmol) 40 (100 μmol)
IICR 50 (10 μmol) 80 (30 μmol) 50 (100 μmol)
NMR (CDCl3) 1.10 (m, 6H), 2.65 (m, 2H), 2.85 (m, 2H), 3.86 (m, 2H), 7.4-7.9 (m, 5H)
TG 71.6 (3 μmol 7.8 (30 μmol)
SOCE 0 (30 μmol) 0 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 40 (100 μmol)
NMR (CDCl3) 1.18 (ms, 9H), 2.84 (m, 2H), 3.04 (m, 2H), 3.74 (m, 2H), 7.2-7.9 (m, 10H)
TG 2.3 (3 μmol) −1.5 (30 μmol
SOCE 0 (30 μmol) 50 (100 μmol)
IICR 50 (10 μmol) 80 (30 μmol) 60 (100 μmol)
2-acetylferrocene (228 mg), isopropylbenzylamine (148 mg), and paraformaldehyde (40 mg) were reacted at 130° C. for 2 hours.
NMR (CDCl3) 1.18 (m, 6H), 2.84 (m, 2H), 3.04 (m, 2H), 3.74 (m, 2H), 7.3-7.9 (m, 10H)
TG 99.2 (3 μmol) 54.2 (30 μmol)
SOCE 0 (30 μmol) 0 (100 μmol)
IICR 50 (10 μmol) 80 (30 μmol) 50 (100 μmol
NMR (CDCl3) 2.08 (m, 6H), 2.97 (m, 2H), 3.5 (m, 2H), 3.9 (m, 2H), 4.21 (m, 2H), 7.4-8.0 (m, 8H)
TG 100 (3 μmol) 60.8 (30 μmol)
SOCE 0 (30 μmol) 10 (100 μmol)
IICR 20 (10 μmol) 40 (30 μmol) 40 (100 μmol)
NMR (CDCl3) 1.75 (m, 2H), 2.36 (m, 2H), 2.83 (m, 4H), 3.76 (m, 4H), 4.52 (s, 4H), 4.78 (s, 4H)
TG 94.9 (3 μmol) 44.1 (30 μmol)
SOCE 10 (30 μmol) 40 (100 μmol)
IICR 40 (10 μmol) 50 (30 μmol) 60 (100 μmol)
NMR (CDCl3) 1.0 (m, 3H), 2.4 (m, 2H), 2.5 (m, 1H), 2.7 (m, 2H), 3.6 (m, 2H), 7-7.5 (m, 5H), 7.66 (s, 1H), 7.7 (s, 1H)
TG 46.9 (3 μmol) 8.1 (30 μmol)
SOCE 0 (30 μmol) 10 (100 μmol)
IICR 40 (10 μmol) 80 (30 μmol) 100 (100 μmol)
NMR (CDCl3) 2.08 (m, 1H), 2.74 (m, 2H), 2.79 (m, 2H), 3.73 (m, 2H), 3.81 (m, 2H), 7.35 (m, 5H), 7.68 (s, 1H), 8.01 (s, 1H)
TG 71.4 (3 μmol) 14.9 (30 μmol)
SOCE 0 (30 μmol) 0 (100 μmol)
IICR 40 (10 μmol) 60 (30 μmol) 90 (100 μmol)
NMR (CDCl3) 2.26 (m, 2H), 2.44 (m, 2H), 2.72 (m, 2H), 7.65 (m, 2H), 7.99 (2H)
TG 61.8 (3 μmol) 14.3 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 40 (10 μmol) 70 (30 μmol) 100 (100 μmol)
NMR (CDCl3) 1.0 (m, 6H), 2.5 (m, 2H), 2.8-9 (m, 2H), 3.5 (m, 2H), 7.0-7.5 (m, 7H)
TG −0.3 (3 μmol) −3.8 (30 μmol)
SOCE 0 (10 μmol) 20 (30 μmol) 40 (100 μmol)
IICR 50 (10 μmol) 80 (30 μmol) 90 (100 μmol)
NMR (CDCl3) 0.9 (t, 3H), 1.44 (m, 2H), 1.49 (m, 2H), 2.2 (m, 2H), 2.9 (m, 2H), 3.7 (m, 2H), 7.1 (1H), 7.49 (1H) 1.0 (m, 3H), 2.4 (m, 2H), 2.5 (m, 1H), 2.7 (m, 2H), 3.6 (m, 2H), 7-7.5 (m, 5H), 7.6 (s, 1H), 7.7 (s, 1H)
TG 35.5 (3 μmol) 5.3 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 10 (100 μmol)
IICR 80 (10 μmol) 50 (30 μmol) 90 (100 μmol)
NMR (CDCl3) 1.1 (m, 9H), 2.5 (m, 2H), 2.9 (m, 2H), 3.8 (m, 2H), 4.4 (m, 2H), 7.11 (m, 2H), 7.44 (m, 2H).
TG 102 (3 μmol) 104 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 10 (100 μmol)
IICR 70 (10 μmol) 40 (30 μmol) 50 (100 μmol)
2-acetyl-1H-benzotriazole (80 mg), isopropylbenzylamine (74.5 mg), and paraformaldehyde (40 mg) were reacted at 130° C. for 2 hours.
NMR (CDCl3) 2.0 (m, 6H), 3.0 (m, 2H), 3.5-3.74 (m, 4H), 4.1 (m, 2H), 7.2-8.0 (m, 9H).
TG 102 (3 μmol) 107 (30 μmol
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 80 (10 μmol) 70 (30 μmol) 60 (100 μmol)
NMR (CDCl3) 2.1 (m, 2H), 2.8 (m, 2H), 3.0 (m, 2H), 3.6 (m, 2H), 4.15 (m, 2H), 6.6 (m, 2H), 7.5 (m, 4H)
TG 105 (3 μmol) 107 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 20 (100 μmol
IICR 0 (10 μmol) 50 (30 μmol) 60 (100 μmol)
4-acetyl biphenyl (392 mg), isopropylbenzylamine (298 mg), and paraformaldehyde (80 mg) were reacted at 130° C. for 2 hours.
NMR (CDCl3) 0.95 (m, 6H), 2.6 (m, 2H), 3.06 (m, 2H), 3.67 (m, 2H), 7-8.1 (m, 14H)
TG 75.7 (3 μmol) 7.1 (30 μmol)
SOCE 20 (10 μmol) 50 (30 μmol) 60 (100 μmol)
IICR 50 (10 μmol) 50 (30 μmol) 90 (100 μmol)
NMR (CDCl3) 1.09 (m, 5H), 2.6 (m, 2H), 2.85 (m, 2H), 3.67 (m, 2H), 3.83 (m, 2H), 3.83 (m, 2H), 7.4-8.0 (m, 7H)
TG 95.1 (3 μmol) 64.9 (30 μmol)
SOCE 20 (10 μmol) 40 (30 μmol) 50 (100 μmol)
IICR 60 (10 μmol) 50 (30 μmol) 60 (100 μmol)
NMR (CDCl3) 2.6 (m, 2H), 3.38 (m, 2H), 4.13 (m, 2H), 4.85 (m, 2H), 7.3-8.1 (m, 14H)
TG 96.4 (3 μmol) 84.3 (30 μmol)
SOCE 20 (10 μmol) 40 (30 μmol) 40 (100 μmol)
IICR 70 (10 μmol) 30 (30 μmol) 30 (100 μmol)
NMR (CDCl3) 2.48 (m, 2H), 2.74 (m, 4H), 3.45 (m, 2H), 6.53 (1H), 7.21 (m, 5H), 7.58 (s, 1H)
TG 105 (3 μmol) 90.5 (30 μmol)
SOCE 20 (30 μmol) 40 (100 μmol)
IICR 30 (10 μmol) 0 (30 μmol) 10 (100 μmol)
NMR (CDCl3) 1.0 (m, 3H), 2.64 (m, 2H), 2.9 (m, 2H), 3.6 (m, 2H), 3.7 (m, 2H), 7.0-7.4 (m, 7H)
TG 74 (0.3 μmol) 33 (1 μmol) 2 (3 μmol) 3.1 (10 μmol) 0.8 (30 μmol)
SOCE 20 (10 μmol) 30 (30 μmol) 40 (100 μmol)
IICR 70 (10 μmol) 70 (30 μmol) 90 (100 μmol)
NMR (CDCl3) 1.25 (d, 9H), 2.64 (t, 2H), 2.97 (t, 2H), 3.73 (m, 2H), 6.9-7.4 (m, 9H)
TG 12.2 (3 μmol) 5.5 (10 μmol) 6.4 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 20 (100 μmol)
IICR 60 (10 μmol) 90 (30 μmol) 90 (100 μmol)
NMR (CDCl3) 1.25 (d, 9H), 2.60 (t, 2H), 2.97 (t, 2H), 3.85 (m, 2H), 7.2-7.9 (m, 9H)
TG 45 (3 μmol) 5 (10 μmol) 0.6 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 20 (10 μmol) 20 (30 μmol) 40 (100 μmol)
NMR (CDCl3) 1.1 (m, 9H), 2.64 (t, 2H), 2.97 (m, 2H), 3.73 (m, 2H), 6.9-7.4 (m, 9H)
TG 11.4 (3 μmol) 2.1 (10 μmol) 4 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 10 (100 μmol)
IICR 90 (10 μmol 100 (30 μmol) 20 (100 μmol)
NMR (CDCl3) 1.25 (d, 9H), 2.62 (t, 2H), 2.90 (t, 2H), 3.73 (m, 2H), 6.9-7.4 (m, 9H)
TG 5 (3 μmol) 0 (10 μmol) −3 (30 μmol)
SOCE 20 (10 μmol) 20 (30 μmol) 60 (100 μmol)
IICR 60 (10 μmol) 70 (30 μmol) 50 (100 μmol)
NMR (CDCl3) 2.42 (m, 2H), 2.465 (m, 2H), 3.48 (m, 3H), 3.67 (m, 2H), 6.94 (s, 1H), 7.4 (s, 1H)
TG 100 (3 μmol) 96 (10 μmol) 84 (30 μmol)
SOCE 10 (10 μmol) 20 (30 μmol) 30 (100 μmol)
IICR 50 (10 μmol) 20 (30 μmol) 30 (100 μmol)
NMR (CDCl3) 2.51 (m, 2H), 2.65 (m, 2H), 3.48 (m, 2H), 3.67 (m, 2H), 7.1 (s, 1H), 7.4 (s, 1H)
TG 93 (3 μmol) 76 (10 μmol) 40 (30 μmol)
SOCE 0 (10 μmol) 10 (30 μmol) 10 (100 μmol)
IICR 30 (10 μmol) 20 (30 μmol) 30 (100 μmol)
NMR (CDCl3) 0.48 (m, 6H), 2.68 (m, 2H), 2.65 (m, 2H), 3.47 (m, 2H), 7.0-8.0 (m, 9H)
TG 8.9 (3 μmol) 2.1 (10 μmol) 3.8 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 10 (100 μmol)
IICR 90 (10 μmol) 100 (30 μmol) 95 (100 μmol)
NMR (CDCl3) 1.09 (m, 6H), 1.85 (m, 2H), 2.65 (m, 2H), 3.45 (m, 2H), 7.80-8.2 (m, 4H)
TG 60 (3 μmol) 2.8 (10 μmol) 6 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 10 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 20 (100 μmol)
NMR (CDCl3) 1.06 (m, 6H), 2.61 (m, 2H), 2.93 (m, 2H), 3.55 (m, 2H), 7.1-8.0 (m, 9H).
TG 19 (3 μmol) 3.6 (10 μmol) 1.6 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 10 (100 μmol)
IICR 80 (10 μmol) 80 (30 μmol) 70 (100 μmol)
NMR (CDCl3) 1.03 (m, 6H), 2.59 (m, 2H), 2.91 (m, 2H), 3.58 (m, 2H), 3.71 (m, 2H), 7.0-7.4 (m, 6H)
TG 31 (3 μmol) 5.6 (10 μmol) 2 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 10 (100 μmol)
IICR 50 (10 μmol) 30 (30 μmol) 50 (100 μmol)
NMR (CDCl3) 2.24 (m, 3H), 2.48 (m, 3H), 2.85 (m, 2H), 3.55 (m, 2H), 6.1 (s, 1H), 7.0-7.4 (m, 6H)
TG 87 (3 μmol) 49 (10 μmol) 12 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 10 (100 μmol)
IICR 20 (10 μmol) 20 (30 μmol) 80 (100 μmol)
NMR (CDCl3) 2.24 (m, 3H), 2.48 (m, 3H), 2.85 (m, 2H), 3.55 (m, 2H), 6.1 (s, 1H), 7.0-7.4 (m, 6H)
TG 87 (3 μmol) 63 (10 μmol) 12 (30 μmol)
SOCE 0 (10 μmol 0 (30 μmol) 30 (100 μmol)
IICR 20 (10 μmol 20 (30 μmol) 30 (100 μmol)
NMR (CDCl3) 1.24 (m, 9H), 2.20 (m, 2H), 2.70 (m, 2H), 3.00 (m, 2H), 3.75 (m, 2H), 7.0-7.4 (m, 7H)
TG 11 (3 μmol) 0.4 (10 μmol) −4.3 (30 μmol)
SOCE 0 (10 μmol) 10 (30 μmol) 20 (100 μmol)
IICR 70 (10 μmol) 70 (30 μmol) 100 (100 μmol
NMR (CDCl3) 1.17 (m, 9H), 2.15 (s, 3H), 2.25 (m, 2H), 2.7 (m, 2H), 3.55 (m, 2H), 6.1 (s, 1H), 6.8-7.4 (m, 7H)
TG 3.4 (3 μmol) −3.9 (10 μmol) −1.5 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 30 (100 μmol)
IICR 80 (10 μmol) 90 (30 μmol) 100 (100 μmol)
NMR (CDCl3) 1.17 (m, 9H), 2.48 (m, 3H), 2.6 (m, 2H), 3.0 (m, 2H), 3.7 (m, 2H), 6.1 (s, 1H), 7.0-7.4 (m, 6H)
TG 2.1 (3 μmol) −5.7 (10 μmol) −4.9 (30 μmol)
SOCE 0 (10 μmol) 10 (30 μmol) 20 (100 μmol
IICR 70 (10 μmol) 80 (30 μmol) 100 (100 μmol
NMR (CDCl3) 1.17 (m, 9H), 2.75 (m, 2H), 2.95 (m, 2H), 3.85 (m, 2H), 7.0-7.6 (m, 8H)
TG 52 (3 μmol) 1.2 (10 μmol) −11.2 (30 μmol)
SOCE 10 (10 μmol) 10 (30 μmol) 30 (100 μmol)
IICR 90 (10 μmol 95 (30 μmol) 100 (100 μmol)
NMR (CDCl3) 0.9-1.5 (m, 6H), 2.5 (m, 3H), 2.75 (m, 2H), 3.55 (m, 2H), 7.0-7.4 (m, 7H)
TG 17.1 (3 μmol) −12 (10 μmol) 8.8 (30 μmol)
SOCE 10 (10 μmol) 20 (30 μmol) 40 (100 μmol)
IICR 10 (10 μmol) 60 (30 μmol) 80 (100 μmol)
NMR (CDCl3) 0.5 (m, 3H), 1.8-2.2 (m, 4H), 3.2 (m, 2H), 2.85 (m, 2H), 3.55 (m, 2H), 6.0-7.3. (m, 7H)
TG 70 (3 μmol) 28 (10 μmol) −2.9 (30 μmol)
SOCE 0 (10 μmol) 10 (30 μmol) 20 (100 μmol)
IICR 20 (10 μmol) 10 (30 μmol) 70 (100 μmol)
NMR (CDCl3) 2.53 (m, 3H), 2.73 (m, 2H), 3.02 (m, 2H), 3.66 (m, 2H), 3.75 (m, 2H), 7.32 (m, 2H)
TG 40 (3 μmol) 12 (10 μmol) 5.9 (30 μmol)
SOCE 20 (10 μmol) 40 (30 μmol) 50 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 70 (100 μmol)
NMR (CDCl3) 0.9-1.1 (m, 6H), 2.48 (m, 3H), 2.55 (m, 2H), 3.2 (m, 2H) 3.55 (m, 2H), 7.0-7.4 (m, 7H)
TG 67 (3 μmol) 27 (10 μmol) −0.4 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 20 (10 μmol) 70 (30 μmol) 100 (100 μmol)
NMR (CDCl3) 2.3 (m, 2H), 2.40 (m, 3H), 2.85 (m, 2H), 3.55 (m, 2H), 3.8 (m, 4H), 7.0-7.4 (m, 12H).
TG 92 (3 μmol) 76 (10 μmol) 25 (30 μmol)
SOCE 0 (10 μmol) 10 (30 μmol) 20 (100 μmol)
IICR 10 (10 μmol) 20 (30 μmol) 30 (100 μmol)
NMR (CDCl3) 2.29 (m, 2H), 2.48 (s, 3H), 2.85 (m, 2H), 3.0 (m, 2H), 3.8 (m, 2H), 7.0-7.4 (m, 7H)
TG 90 (3 μmol) 88 (10 μmol) 54 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol 30 (100 μmol)
IICR 30 (10 μmol) 50 (30 μmol) 30 (100 μmol)
NMR (CDCl3) 1.17 (m, 9H), 2.75 (m, 2H), 2.95 (m, 2H), 3.8 (m, 2H), 7.0-7.4 (m, 9H)
TG −6 (3 μmol) −12.2 (10 μmol) −5.7 (30 μmol
SOCE 20 (10 μmol) 20 (30 μmol) 20 (100 μmol)
IICR 50 (10 μmol) 40 (30 μmol) 40 (100 μmol)
NMR (CDCl3) 2.5 (m, 2H), 2.9 (m, 2H), 3.55 (m, 4H), 7.0-7.4 (m, 12H)
TG 43 (3 μmol) 11 (10 μmol) −4 (30 μmol)
SOCE 0 (10 μmol) 20 (30 μmol) 40 (100 μmol)
IICR 20 (10 μmol) 20 (30 μmol) 50 (100 μmol)
NMR (CDCl3) 2.24 (m, 2H), 2.48 (m, 2H), 2.85 (m, 2H), 3.55 (m, 3H), 7.0-7.4 (m, 7H)
TG 23 (3 μmol) 4.2 (10 μmol) −11.7 (30 μmol)
SOCE 10 (10 μmol) 30 (30 μmol) 60 (100 μmol)
IICR 40 (10 μmol) 10 (30 μmol) 40 (100 μmol)
NMR (CDCl3) 2.8 (m, 2H), 3.0 (m, 2H), 3.7 (m, 2H), 3.55 (m, 2H), 3.8 (m, 2H) 7.0-7.4 (m, 7H)
TG 31 (3 μmol) 0.7 (10 μmol 2.8 (30 μmol
SOCE 20 (10 μmol 20 (30 μmol) 30 (100 μmol)
IICR 70 (10 μmol) 10 (30 μmol) 40 (100 μmol)
NMR (CDCl3) 2.41 (m, 2H), 2.48 (m, 3H), 2.85 (m, 2H), 3.55 (m, 2H), 3.8 (m, 2H), 7.1 (s, 1H) 7.4 (s, 1H)
TG 57 (3 μmol) 21.1 (10 μmol) 2.1 (30 μmol)
SOCE 10 (10 μmol) 10 (30 μmol 0 (100 μmol)
IICR 0 (10 μmol) 10 (30 μmol) 80 (100 μmol)
NMR (CDCl3) 1.1 (m, 6H), 2.44 (m, 2H), 2.58 (m, 2H), 2.85 (m, 2H), 3.9 (m, 2H), 6.1 (s, 1H), 7.4 (s, 1H)
TG 35 (3 μmol) 9.1 (10 μmol) −13.7 (30 μmol)
SOCE 20 (10 μmol) 20 (30 μmol) 10 (100 μmol)
IICR 0 (10 μmol) 10 (30 μmol) 50 (100 μmol)
NMR (CDCl3) 2.54 (m, 2H), 2.75 (m, 2H), 3.04 (m, 2H), 3.65-3.8 (m, 6H), 7.1 (s, 1H), 7.4 (s, 1H)
TG 30 (3 μmol) 4.6 (10 μmol) −3.3 (30 μmol)
SOCE 10 (10 μmol) 10 (30 μmol) 20 (100 μmol)
IICR 30 (10 μmol) 40 (30 μmol) 50 (100 μmol)
NMR (CDCl3), 1.05 (m, 3H), 2.5 (m, 4H), 2.9 (m, 2H), 3.65 (m, 4H), 7.1 (s, 1H), 7.4 (s, 1H)
TG 89 (3 μmol) 64 (10 μmol) 10 (30 μmol)
SOCE 0 (10 μmol) 10 (30 μmol) 20 (100 μmol)
IICR 0 (10 μmol) 10 (30 μmol) 70 (100 μmol)
NMR (CDCl3) 1.16 (m, 9H), 2.48 (m, 2H), 2.85 (m, 2H), 3.55 (m, 4H), 7.1 (s, 1H), 7.4 (s, 1H)
TG 33 (3 μmol) 4.6 (10 μmol) −6.6 (30 μmol)
SOCE 0 (10 μmol) 10 (30 μmol) 20 (100 μmol)
IICR 0 (10 μmol) 10 (30 μmol) 50 (100 μmol)
NMR (CDCl3) 1.73 (m, 4H), 2.48 (m, 2H), 2.60 (m, 2H), 3.70 (m, 2H), 7.1 (s, 1H), 7.4 (s, 1H)
TG 62 (3 μmol) 37 (10 μmol) 2.3 (30 μmol)
SOCE 20 (10 μmol) 30 (30 μmol) 20 (100 μmol)
IICR 0 (10 μmol) 30 (30 μmol) 50 (100 μmol)
NMR (CDCl3) 2.5 (m, 4H), 2.58 (m, 2H), 2.65 (m, 2H), 3.55-3.7 (m, 4H), 7.1 (s, 1H), 7.4 (s, 1H)
TG 57 (3 μmol) 26 (10 μmol) 9.0 (30 μmol)
SOCE 30 (10 μmol) 30 (30 μmol) 40 (100 μmol)
IICR 20 (10 μmol) 0 (30 μmol) 60 (100 μmol)
NMR (CDCl3) 2.1 (m, 2H), 2.48 (m, 4H), 2.85 (m, 2H), 3.55 (m, 2H), 7.1 (s, 1H), 7.4 (s, 1H)
TG 93 (3 μmol) 56 (10 μmol) 12 (30 μmol)
SOCE 20 (10 μmol 30 (30 μmol) 50 (100 μmol)
IICR 10 (10 μmol 50 (30 μmol) 70 (100 μmol)
NMR (CDCl3) 1.59 (m, 2H), 2.48 (m, 2H), 2.71 (m, 1H), 7.1-7.4 (m, 6H)
TG 102 (3 μmol) 101 (10 μmol) 100 (30 μmol)
SOCE 10 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 20 (10 μmol) 10 (30 μmol) 60 (100 μmol)
NMR (CDCl3), 0.95 (m, 3H), 1.38-1.5 (m, 4H), 245 (m, 2H), 3.33 (m, 2H), 6.5-7.4 (m, 7H)
TG 112 (3 μmol) 84.6 (10 μmol) 54.7 (30 μmol)
SOCE 20 (10 μmol) 30 (30 μmol) 40 (100 μmol)
IICR 50 (10 μmol) 20 (30 μmol) 0 (100 μmol)
NMR (CDCl3), 0.7 (m, 6H), 1.2-1.4 (m, 8H), 2.35 (m, 2H), 2.55 (m, 2H), 2.7 (m, 2H), 7.1 (s, 1H), 7.4 (s, 1H).
TG 22 (3 μmol) 4.4 (10 μmol) 7.0 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 24 (100 μmol)
IICR 50 (10 μmol) 50 (30 μmol) 60 (100 μmol)
NMR (CDCl3), 0.86-1.0 (m, 16H), 2.48 (m, 2H), 2.85 (m, 2H), 71 (s, 1H), 7.4 (s, 1H)
TG 2.3 (3 μmol) −4.3 (10 μmol −10 (30 μmol)
SOCE 0 (10 μmol) 8 (30 μmol) 61 (100 μmol)
IICR 50 (10 μmol) 80 (30 μmol) 60 (100 μmol)
2-acetyl-5-bromothiophene (230 mg), cystamine (122 mg), paraformaldehyde (64 mg), and dioxane (0.4 mL) were heated at 110° C. for 30 minutes.
NMR (CDCl3) 1.15 (m, 2H), 2.52 (m, 4H), 3.13 (m, 4H), 3.40 (m, 4H), 3.72 (m, 4H), 7.2 (s, 2H), 7.4 (s, 2H)
TG 0.8 (3 μmol) 2.5 (10 μmol) 4.3 (30 μmol)
SOCE 0 (10 μmol) 18 (30 μmol) 65 (100 μmol)
IICR 0 (10 μmol) 40 (30 μmol) 60 (100 μmol)
NMR (CDCl3) 2.54-2.9 (m, 4H), 3.7-3.79 (m, 8H), 6.48 (s, 1H), 6.99 (s, 1H), 7.1 (s, 1H), 7.46 (m, 2H)
TG 101 (3 μmol) 96 (10 μmol) 55 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 21 (100 μmol)
IICR 0 (10 μmol) 10 (30 μmol) 30 (100 μmol)
NMR (CDCl3) 3.61 (m, 2H), 3.7 (m, 2H), 3.9 (m, 2H), 4.2 (m, 2H), 7.0-7.4 (m, 7H)
TG 120 (3 μmol) 105 (10 μmol) 94 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 34 (100 μmol)
IICR 0 (10 μmol) 20 (30 μmol) 40 (100 μmol)
NMR (CDCl3) 2.16 (m, 2H), 2.51 (m, 2H), 2.85 (m, 2H), 3.55 (m, 4H), 6.8-7.6 (m, 4H)
TG 37 (3 μmol) 20 (10 μmol) −4.3 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 26 (100 μmol)
IICR 50 (10 μmol) 70 (30 μmol) 80 (100 μmol)
NMR (CDCl3), 1.50 (m, 2H), 1.61 (m, 4H), 2.1-2.8 (m, 4H), 3.22-3.36 (m, 4H), 6.1 (s, 1H), 7.4 (s, 1H)
TG 82 (3 μmol) 48 (10 μmol) 30 (30 μmol)
SOCE 0 (10 μmol) 2 (30 μmol) 6 (100 μmol)
IICR 10 (10 μmol) 40 (30 μmol) 30 (100 μmol)
NMR (CDCl3) 2.1-2.48 (m, 2H), 2.85 (m, 2H), 37 (m, 2H), 7.1 (s, 1H), 7.4 (s, 1H)
TG 75 (3 μmol) 44 (10 μmol) 12.9 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 10 (100 μmol)
IICR 0 (10 μmol) 20 (30 μmol) 70 (100 μmol)
NMR (CDCl3) 1.16 (m, 3H), 2.8 (m, 2H), 2.8-4.0 (m, 12H), 7.1-7.4 (m, 4H)
TG 51 (3 μmol) 24 (10 μmol) 10 (30 μmol)
SOCE 0 (10 μmol) 1 (30 μmol) 35 (100 μmol)
IICR 10 (10 μmol) 30 (30 μmol) 90 (100 μmol)
NMR (CDCl3) 1.59 (m, 1H), 2.51 (m, 2H), 2.71 (m, 2H), 3.55 (m, 2H), 7.1-7.4 (m, 6H)
TG 95 (3 μmol) 102 (10 μmol) 86 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 0 (10 μmol) 20 (30 μmol) 50 (100 μmol)
NMR (CDCl3) 1.43 (m, 6H), 2.38 (m, 6H), 3.62 (m, 2H), 7.1 (m, 1H), 7.4 (s, 1H)
TG 82 (3 μmol) 63 (10 μmol) 26 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 16 (100 μmol)
IICR 20 (10 μmol) 0 (30 μmol) 20 (100 μmol)
NMR (CDCl3) 2.51 (m, 2H), 2.86 (m, 2H), 3.65 (m, 2H), 7.1-7.4 (m, 7H)
TG 99 (3 μmol) 96 (10 μmol) 78 (30 μmol)
SOCE 46 (10 μmol) 0 (30 μmol) 0 (100 μmol)
IICR 20 (10 μmol) 0 (30 μmol) 50 (100 μmol)
NMR (CDCl3) 1.47 (m, 2H), 1.68 (m, 2H), 1.85 (m, 2H), 2.15 (m, 2H), 2.52 (m, 2H), 3.50 (m, 2H), 7.1-7.4 (m, 2H)
TG 46 (3 μmol) 17.4 (10 μmol) 6.6 (30 μmol)
SOCE 10 (10 μmol) 2 (30 μmol) 3 (100 μmol)
IICR 60 (10 μmol) 50 (30 μmol) 70 (100 μmol)
NMR (CDCl3) 2.51 (m, 2H), 2.74 (m, 4H), 3.4 (m, 2H), 7.21-7.4 (m, 7H)
TG 92 (3 μmol) 73 (10 μmol) 26 (30 μmol)
SOCE 0 (10 μmol) 9 (30 μmol) 32 (100 μmol
IICR 30 (10 μmol) 0 (30 μmol) 0 (100 μmol)
NMR (CDCl3) 1.62 (m, 2H), 2.51 (m, 2H), 2.99 (m, 2H), 3.86 (m, 2H), 4.39 (m, 2H), 7.11 (s, 1H), 7.4 (s, 1H)
TG 110 (3 μmol) 107 (10 μmol) 98 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 34 (100 μmol)
IICR 30 (10 μmol) 0 (30 μmol) 0 (100 μmol)
NMR (CDCl3) 2.5 (m, 2H), 2.9 (m, 2H), 3.55 (m, 2H), 4.7 (m, 2H), 7.1-7.4 (m, 6H)
TG 109 (3 μmol) 107 (10 μmol) 96 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 7 (100 μmol)
IICR 60 (10 μmol) 0 (30 μmol 20 (100 μmol)
NMR (CDCl3) 1.8 (m, 1H), 2.3 (m, 2H), 2.6 (m, 6H), 3.0 (m, 4H), 7.1-7.4 (m, 4H)
TG 66 (3 μmol) 32.6 (10 μmol) 13.6 (30 μmol)
SOCE 0 (10 μmol) 10 (30 μmol) 10 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 60 (100 μmol)
NMR (CDCl3) 1.9 (m, 2H), 2.48 (m, 2H), 3.37 (m, 1H), 3.70 (m, 1H), 3.9 (m, 2H), 6.9-7.4 (m, 12H)
TG 109 (3 μmol) 99 (10 μmol) 79 (30 μmol)
SOCE 0 (10 μmol) 16 (30 μmol) 16 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 50 (100 μmol)
NMR (CDCl3) 1.64 (m, 4H), 2.51 (m, 4H), 3.35 (m, 4H), 3.7 (m, 4H), 6.8-7.4 (m, 4H)
TG 93 (3 μmol) 22.6 (10 μmol) 3.6 (30 μmol)
SOCE 0 (10 μmol) 3 (30 μmol) 10 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 10 (100 μmol)
NMR (CDCl3) 2.51 (m, 2H), 2.476 (m, 2H), 3.24 (m, 2H), 3.71 (m, 2H), 4.34 (m, 2H), 6.5-7.4 (m, 7H)
TG 102 (3 μmol) 77 (10 μmol) 4 (30 μmol)
SOCE 0 (10 μmol) 9 (30 μmol) 47 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 70 (100 μmol)
NMR (CDCl3) 2.67 (m, 2H), 3.12 (m, 2H), 3.70 (m, 2H), 4.32 (m, 2H), 7.1 (s, 1H), 7.4 (s, 1H)
TG 95 (3 μmol) 72 (10 μmol) 31 (30 μmol)
SOCE 0 (10 μmol) 4 (30 μmol) 23 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 70 (100 μmol)
NMR (CDCl3), 2.51 (m, 2H), 3.42 (m, 2H), 4.17 (m, 2H), 4.57 (m, 2H), 6.1-7.7 (m, 7H)
TG 113 (3 μmol) 105 (10 μmol) 94 (30 μmol)
SOCE 0 (10 μmol) 24 (30 μmol) 57 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 70 (100 μmol)
NMR (CDCl3), 1.21 (m, 3H), 1.60 (m, 2H), 2.51 (m, 2H), 3.540 (m, 2H), 4.43 (m, 2H), 7.1 (s, 1H), 7.4 (s, 1H)
TG 99 (3 μmol) 76 (10 μmol) 46 (30 μmol)
SOCE 10 (10 μmol) 0 (30 μmol) 20 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 70 (100 μmol)
NMR (CDCl3), 1.35 (m, 2H), 1.65 (m, 4H), 2.50 (m, 2H), 3.50 (m, 2H), 3.66 (m, 2H), 4.03 (m, 2H), 4.33 (m, 2H), 7.1 (s, 1H), 7.4 (s, 1H)
TG 103 (3 μmol) 75 (10 μmol) 38 (30 μmol)
SOCE 22 (10 μmol) 2 (30 μmol) 19 (100 μmol)
IICR 22 (10 μmol) 0 (30 μmol) 19 (100 μmol)
NMR (CDCl3), 0.9 (m, 3H), 1.51 (m, 2H), 3.28 (m, 2H), 4.49 (m, 2H), 7.1 (s, 1H), 7.4 (s, 1H)
TG 109 (3 μmol) 96 (10 μmol) 72 (30 μmol)
SOCE 11 (10 μmol) 13 (30 μmol) 23 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 70 (100 μmol)
NMR (CDCl3), 2.29 (m, 2H), 2.3-2.7 (m, 10H), 7.1 (s, 1H), 7.4 (s, 1H)
TG 80 (3 μmol) 42 (10 μmol) 16 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 14 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 70 (100 μmol)
NMR (CDCl3), 1.56 (m, 2H), 2.51 (m, 2H), 7.1 (s, 1H), 7.26 (m, 2H), 7.4 (s, 1H),
TG 102 (3 μmol 66 (10 μmol) 3.6 (30 μmol)
SOCE 24 (10 μmol) 49 (30 μmol) 70 (100 μmol)
IICR 0 (10 μmol 0 (30 μmol) 40 (100 μmol)
NMR (CDCl3), 0.93 (m, 3H), 1.50 (m, 2H), 2.17 (m, 2H), 2.50 (m, 2H), 3.50 (m, 2H), 4.45 (m, 2H), 7.1 (s, 1H), 7.4 (s, 1H)
TG 55.9 (3 μmol 22.6 (10 μmol) 3.6 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 10 (100 μmol
IICR 0 (10 μmol 0 (30 μmol) 70 (100 μmol)
NMR (CDCl3) 1.75 (m, 2H), 2.50 (m, 2H), 3.50-3.67 (m, 4H), 7.0 (s, 2H), 7.4 (s, 2H)
TG 5 (3 μmol) 6.3 (30 μmol)
SOCE 6 (10 μmol) 0 (30 μmol 90 (100 μmol)
IICR 0 (10 μmol 0 (30 μmol) 70 (100 μmol)
NMR (CDCl3) 1.61 (m, 4H), 2.6 (m, 4H), 3.43 (m, 4H), 3.71 (m, 4H), 7.4-8.0 (m, 8H)
TG 18 (3 μmol 9.1 (30 μmol
SOCE 0 (10 μmol) 17 (30 μmol) 96 (100 μmol)
IICR 0 (10 μmol 0 (30 μmol) 70 (100 μmol)
NMR (CDCl3) 1.78 (m, 4H), 3.45 (m, 8H), 3.71 (m, 4H), 7.3-8.0 (m, 10H)
TG 63 (3 μmol) 10 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 90 (100 μmol)
IICR 0 (10 μmol) 50 (30 μmol 81 (100 μmol)
NMR (CDCl3) 1.56 (m, 8H), 2.58 (m, 4H), 3.71 (m, 4H), 7.14-7.70 (m, 6H)
TG 95.1 (3 μmol) −64.9 (30 μmol)
SOCE 20 (10 μmol) 40 (30 μmol) 50 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 70 (100 μmol)
NMR (CDCl3) 2.0 (m, 2H), 2.74 (m, 8H), 3.5-4.0 (m, 8H), 7.3-8.4 (m, 14H)
TG 36 (3 μmol) 1.6 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 3 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 29 (100 μmol)
NMR (CDCl3) 1.57 (m, 2H), 2.64 (m, 8H), 3.5 (m, 4H), 3.67 (m, 4H), 7.4-9.2 (m, 8H)
TG 24 (3 μmol) 3.3 (30 μmol)
SOCE 5 (10 μmol) 0 (30 μmol) 71 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 21 (100 μmol)
NMR (CDCl3) 1.56 (m, 4H), 2.49 (m, 4H), 3.71 (m, 8H), 6.5 (m, 2H), 7.26 (m, 2H), 7.58 (m, 2H),
TG 13 (3 μmol) −1.5 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 15 (100 μmol)
IICR 0 (10 μmol) 54 (30 μmol) 58 (100 μmol)
NMR (CDCl3) 0.84 (m, 3H), 1.82 (m, 4H), 2.51 (m, 4H), 2.7 (m, 2H), 3.53 (m, 2H), 7.0-7.8 (m, 2H)
TG 11 (3 μmol) 4.7 (30 μmol
SOCE 100 (10 μmol) 28 (30 μmol) 65 (100 μmol
IICR 0 (10 μmol) 36 (30 μmol) 0 (100 μmol)
NMR (CDCl3) 0.91.09 (m, 3H), 1.3-1.4 (m, 4H), 2.3 (m, 2H), 2.4 (m, 2H), 3.6 (m, 2H), 3.9 (m, 2H), 7.0-7.5 (m, 7H)
TG 12 (3 μmol) 0 (30 μmol
SOCE 0 (10 μmol 0 (30 μmol) 53 (100 μmol)
IICR 0 (10 μmol) 8 (30 μmol) 0 (100 μmol)
NMR (CDCl3) 0.8 (m, 3H), 1.3-1.5 (m, 4H), 2.3 (m, 2H), 2.6 (m, 2H), 3.0 (m, 2H), 3.6 (m, 2H), 7.0-7.8 (m, 9H)
TG 54 (3 μmol) 9.8 (30 μmol)
SOCE 4 (10 μmol) 0 (30 μmol) 40 (100 μmol)
IICR 0 (10 μmol) 33 (30 μmol 0 (100 μmol)
NMR (CDCl3) 0.9 (m, 3H), 1.2-1.4 (m, 4H), 2.3 (m, 2H), 2.5 (m, 2H), 2.8 (m, 2H), 3.5 (m, 2H), 6.8-7.5 (m, 9H)
TG 19 (3 μmol) 0.2 (30 μmol
SOCE 21 (10 μmol) 0 (30 μmol) 27 (100 μmol)
IICR 18 (10 μmol) 84 (30 μmol) 51 (100 μmol)
NMR (CDCl3) 0.9 (m, 3H), 1.2-1.4 (m, 4H), 2.5 (m, 2H), 2.9 (m, 2H), 3.6 (m, 2H), 3.83 (m, 2H), 7.0-7.5 (m, 8H)
TG 27 (3 μmol) 0.2 (30 μmol
SOCE 21 (10 μmol) 0 (30 μmol) 27 (100 μmol)
IICR 22 (10 μmol) 20 (30 μmol) 36 (100 μmol)
NMR (CDCl3) 0.9 (m, 3H), 1.3-1.4 (m, 4H), 2.5 (m, 2H), 2.7 (m, 2H), 3.7 (m, 2H), 7.1-8.0 (m, 12H)
TG 93 (3 μmol) 7.6 (30 μmol)
SOCE 0 (10 μmol) 0 (30 μmol) 41 (100 μmol)
IICR 50 (10 μmol) 24 (30 μmol) 46 (100 μmol)
NMR (CDCl3) 2.5 (m, 2H), 2.98 (m, 2H), 3.71 (m, 2H), 3.81 (m, 2H), 4.31 (m, 2H), 7.2-7.4 (m, 8H)
TG 81 (3 μmol) 71 (10 μmol) 56 (30 μmol)
SOCE 20 (10 μmol) 40 (30 μmol) 50 (100 μmol)
IICR 50 (10 μmol) 24 (30 μmol) 46 (100 μmol)
NMR (CDCl3) 2.60 (m, 4H), 3.4 (m, 4H), 3.6-3.8 (m, 8H), 7.4-8.0 (m, 7H)
TG 25 (3 μmol) 4.2 (30 μmol)
SOCE 4 (10 μmol) 31 (30 μmol) 70 (100 μmol)
IICR 10 (10 μmol) 76 (30 μmol) 81 (100 μmol)
NMR (CDCl3) 1.57 (m, 8H) 2.68 (m, 4H), 7.28 (s, 2H)
TG 60 (3 μmol) 27 (30 μmol)
SOCE 6 (10 μmol 0 (30 μmol) 39 (100 μmol)
IICR 51 (10 μmol) 51 (30 μmol) 74 (100 μmol)
NMR (CDCl3) 2.5 (m, 2H), 3.4 (m, 2H), 3.7 (m, 2H), 7.0-7.4 (m, 7H)
TG 86 (3 μmol) 14.1 (30 μmol)
SOCE 0 (10 μmol) 10 (30 μmol) 20 (100 μmol)
IICR 0 (10 μmol) 10 (30 μmol) 50 (100 μmol)
NMR (CDCl3) 0.87 (m, 6H), 1.22 (m, 2H), 3.7 (m, 2H), 7.0-7.4 (m, 7H)
TG 27 (3 μmol) 11.2 (10 μmol) 4.2 (30 μmol)
SOCE 25 (10 μmol) 16 (30 μmol) 46 (100 μmol)
IICR 0 (10 μmol) 5 (30 μmol) 0 (100 μmol)
NMR (CDCl3) 2.5 (m, 2H), 3.4 (m, 2H), 3.7 (m, 2H), 7.0-7.4 (m, 7H)
TG 16 (3 μmol) 4.9 (10 μmol) 4.2 (30 μmol
SOCE 0 (10 μmol) 10 (30 μmol) 100 (100 μmol)
IICR 0 (10 μmol) 35 (30 μmol) 70 (100 μmol)
NMR (CDCl3) 0.98 (m, 6H), 1.25 (m, 16H), 2.1-2.38 (m, 6H), 6.96 (s, 1H), 7.47 (s, 1H)
TG 13 (3 μmol) 6.1 (10 μmol) 6.3 (30 μmol)
SOCE 0 (10 μmol) 95 (30 μmol) 53 (100 μmol)
IICR 0 (10 μmol) 14 (30 μmol) 0 (100 μmol)
2-acetyl-5-bromothiophene (34.3 mg), cystinedimethylester (23.3 mg), paraformaldehyde (6.7 mg), and dioxane (0.2 mL) were heated for 30 minutes to 110° C.
NMR (CDCl3) 2.02 (m, 2H), 2.51 (m, 4H), 2.93 (m, 4H), 3.15 (m, 4H), 3.4 (m, 2H), 3.79 (m, 6H), 7.1 (s, 2H), 7.4 (s, 2H).
TG 4.6 (3 μmol) 2.9 (10 μmol) 14 (30 μmol)
SOCE 20 (10 μmol) 40 (30 μmol) 50 (100 μmol)
IICR 44 (10 μmol) 72 (30 μmol) 77 (100 μmol)
NMR (CDCl3) 2.25 (m, 2H), 3.4 (m, 2H), 3.7 (m, 3H), 5.31 (m, 2H) 7.0-7.4 (m, 2H)
TG 4.6 (3 μmol) 11 (10 μmol) 18 (30 μmol)
SOCE 20 (10 μmol) 40 (30 μmol) 50 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 70 (100 μmol)
NMR (CDCl3) 2.0 (m, 2H), 2.0 (m, 2H) 2.60 (m, 2H), 2.9 (m, 2H), 5.30-5.31 (m, 2H), 1 (m, 2H), 7.1-7.34 (m, 4H)
TG 14 (3 μmol) 10 (10 μmol) 13 (30 μmol)
SOCE 20 (10 μmol) 40 (30 μmol) 50 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 70 (100 μmol)
NMR (CDCl3) 3.1 (m, 4H), 3.7 (m, 8H), 3.9 (m, 4H), 6.57 (m, 2H), 7.25 (m, 2H), 7.67 (m, 2H),
TG 9.7 (3 μmol) 2.7 (10 μmol) −3.8 (30 μmol)
SOCE 20 (10 μmol) 40 (30 μmol) 50 (100 μmol)
IICR 22 (10 μmol) 45 (30 μmol) 54 (100 μmol)
NMR (CDCl3) 0.9-12 (m, 6H), 2.5 (m, 2H), 2.8 (m, 2H), 3.6 (m, 2H), 7.0-7.5 (m, 7H)
TG 16 (3 μmol) 4.6 (10 μmol) 1.6 (30 μmol)
SOCE 20 (10 μmol) 40 (30 μmol) 50 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 70 (100 μmol)
NMR (CDCl3) 2.74 (m, 2H), 3.71 (m, 2H), 3.81 (m, 2H), 7.59-8.4 (m, 7H),
TG 33 (3 μmol) 6.4 (10 μmol) 29 (30 μmol)
SOCE 20 (10 μmol) 40 (30 μmol) 50 (100 μmol)
IICR 6 (10 μmol) 37 (30 μmol) 41 (100 μmol)
NMR (CDCl3) 2.59 (m, 4H), 3.5 (m, 4H), 3.71 (m, 4H), 3.88 (m, 6H), 7.6 (m, 4H), 7.84 (m, 4H),
TG 25 (3 μmol) 3.7 (10 μmol) 2.3 (30 μmol)
SOCE 20 (10 μmol 40 (30 μmol) 50 (100 μmol)
IICR 58 (10 μmol) 61 (30 μmol) 76 (100 μmol)
NMR (CDCl3) 2.34 (m, 2H), 2.54 (m, 2H), 2.6 (m, 3H), 7.74 (m, 2H), 8.82 (m, 2H),
TG 54 (3 μmol) 16 (10 μmol) 3.5 (30 μmol)
SOCE 20 (10 μmol) 40 (30 μmol) 50 (100 μmol)
IICR 44 (10 μmol) 42 (30 μmol) 21 (100 μmol)
NMR (CDCl3) 2.67 (m, 3H), 3.26 (m, 2H), 3.74 (m, 4H), 7.44 (m, 2H), 7.94 (m, 3H),
TG 94 (3 μmol) 82 (10 μmol 60 (30 μmol)
SOCE 20 (10 μmol) 40 (30 μmol) 50 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 70 (100 μmol)
NMR (CDCl3) 0.88 (m, 9H), 2.5 (m, 2H), 3.7 (m, 2H), 7.11 (m, 1H), 7.27 (m, 1H),
TG 22 (3 μmol) 12 (10 μmol) 4.7 (30 μmol)
SOCE 20 (10 μmol) 40 (30 μmol) 50 (100 μmol)
IICR 14 (10 μmol) 67 (30 μmol) 83 (100 μmol)
NMR (CDCl3) 0.85-1.03 (m, 9H), 2.51 (m, 2H), 2.96 (m, 2H), 6.96 (m, 1H), 7.47 (m, 1H),
TG 41 (3 μmol) 18 (10 μmol) 6.7 (30 μmol)
SOCE 20 (10 μmol) 40 (30 μmol) 50 (100 μmol)
IICR 2 (10 μmol) 72 (30 μmol) 83 (100 μmol)
NMR (CDCl3) 1.03 (m, 12H), 3.7 (m, 2H), 3.9 (m, 2H), 7.74 (m, 2H), 8.8 (m, 2H),
TG 103 (3 μmol) 96 (10 μmol) 75 (30 μmol)
SOCE 20 (10 μmol) 40 (30 μmol) 50 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 10 (100 μmol)
NMR (CDCl3) 1.56 (m, 4H), 2.65 (m, 4H), 3.7 (m, 4H), 7.78 (s, 4H), 8.03 (s, 4H),
TG 33 (3 μmol) 12 (10 μmol) 2.6 (30 μmol)
SOCE 20 (10 μmol) 40 (30 μmol) 50 (100 μmol)
IICR 1 (10 μmol) 44 (30 μmol) 80 (100 μmol)
NMR (CDCl3) 2.64 (m, 4H), 3.69 (m, 8H), 3.75 (m, 8H), 7.27 (m, 4H), 8.03 (m, 4H),
TG 36 (3 μmol) 13 (10 μmol) 2.9 (30 μmol
SOCE 20 (10 μmol) 40 (30 μmol) 50 (100 μmol)
IICR 0 (10 μmol) 0 (30 μmol) 70 (100 μmol)
NMR (CDCl3) 2.73 (m, 4H), 3.59 (m, 4H), 3.70 (m, 6H), 3.9 (m, 4H), 7.68 (m, 2H), 8.01 (m, 2H),
TG 73 (3 μmol) 52 (10 μmol) 25 (30 μmol)
SOCE 20 (10 μmol) 40 (30 μmol) 50 (100 μmol)
IICR 19 (10 μmol) 0 (30 μmol) 13 (100 μmol)
NMR (CDCl3) 2.46 (m, 4H), 3.3 (m, 4H), 3.7 (m, 14H), 6.53 (m, 2H), 7.26 (m, 2H), 7.57 (m, 2H),
TG 17 (3 μmol) 7.9 (10 μmol) 3.7 (30 μmol)
SOCE 20 (10 μmol) 40 (30 μmol) 50 (100 μmol)
IICR 31 (10 μmol) 1 (30 μmol) 57 (100 μmol)
NMR (CDCl3) 2.73 (m, 4H), 3.35 (m, 4H), 3.46 (m, 4H), 7.26 (m, 2H), 8.65 (m, 2H), 8.76 (m, 2H),
TG 67 (3 μmol) 34 (10 μmol) 10 (30 μmol)
SOCE 20 (10 μmol) 40 (30 μmol) 50 (100 μmol)
IICR 39 (10 μmol) 12 (30 μmol) 28 (100 μmol)
NMR (CDCl3) 2.54 (m, 4H), 2.67 (m, 4H), 3.71 (m, 6H), 3.85 (m, 4H), 6.94 (m, 2H), 7.52 (m, 2H),
TG 17 (3 μmol) 4.4 (10 μmol) 2 (30 μmol)
SOCE 20 (10 μmol) 40 (30 μmol) 50 (100 μmol)
IICR 57 (10 μmol) 17 (30 μmol) 83 (100 μmol)
NMR (CDCl3) 2.67 (m, 4H), 3.71 (m, 6H), 3.80 (m, 4H), 3.97 (m, 8H), 7.4-8.05 (m, 16H)
TG 60 (3 μmol) 16 (10 μmol) 0.3 (30 μmol)
SOCE 20 (10 μmol) 40 (30 μmol) 50 (100 μmol)
IICR 54 (10 μmol) 84 (30 μmol) 94 (100 μmol)
NMR (CDCl3) 1.17 (m, 9H), 2.53 (m, 2H), 2.96 (m, 2H), 3.71 (m, 2H), 7.1-7.5 (m, 7H)
TG 2.6 (3 μmol) 0.8 (10 μmol) −3.3 (30 μmol)
SOCE 20 (10 μmol) 40 (30 μmol) 50 (100 μmol)
IICR 78 (10 μmol) 73 (30 μmol) 35 (100 μmol)
NMR (CDCl3) 2.52 (m, 8H), 3.71 (m, 6H), 3.9 (m, 4H), 7.3 (m, 4H)
TG 35 (3 μmol) 14 (10 μmol) 7.1 (30 μmol)
SOCE 20 (10 μmol) 40 (30 μmol) 50 (100 μmol)
IICR 49 (10 μmol) 43 (30 μmol) 62 (100 μmol)
NMR (CDCl3) 1.17 (s, 9H), 2.93 (m, 2H), 3.0 (m, 2H), 3.73 (m, 2H), 6.9-7.5 (m, 7H)
TG 9.4 (3 μmol) 2.5 (10 μmol) 2.1 (30 μmol)
SOCE 20 (10 μmol) 40 (30 μmol) 50 (100 μmol)
IICR 89 (10 μmol) 83 (30 μmol) 77 (100 μmol)
NMR (CDCl3) 1.1 (m, 9H), 3.0 (m, 2H), 3.1 (m, 2H), 3.75 (m, 2H), 7.0-8.1 (m, 8H)
TG 2.8 (3 μmol) 4.1 (10 μmol) 3.3 (30 μmol)
SOCE 20 (10 μmol) 40 (30 μmol) 50 (100 μmol)
IICR 76 (10 μmol) 83 (30 μmol) 77 (100 μmol)
NMR (CDCl3) 2.15 (m, 2H), 2.5 (m, 3H), 2.67 (m, 2H), 2.8 (m, 2H), 3.6 (m, 2H), 3.83 (m, 3H), 7.0-7.5 (m, 2H)
TG 9.3 (3 μmol) 6.1 (10 μmol) 7.9 (30 μmol)
SOCE 20 (10 μmol 40 (30 μmol) 50 (100 μmol
IICR 26 (10 μmol) 76 (30 μmol 81 (100 μmol)
NMR (CDCl3) 2.5 (m, 4H), 3.5 (m, 4H), 3.6 (m, 2H), 7.25 (m, 2H)
TG 11 (3 μmol) 5.6 (10 μmol) 3.3 (30 μmol)
SOCE 20 (10 μmol) 40 (30 μmol) 50 (100 μmol)
IICR 59 (10 μmol) 65 (30 μmol) 88 (100 μmol)
NMR (CDCl3) 0.9-1.4 (m, 16H), 2.55 (m, 2H), 2.8 (m, 2H), 2.9 (m, 2H), 7.2-7.4 (m, 2H)
TG 3.9 (3 μmol) 5.6 (10 μmol) −4.4 (30 μmol)
SOCE 20 (10 μmol) 40 (30 μmol) 50 (100 μmol)
IICR 76 (10 μmol) 80 (30 μmol) 82 (100 μmol
NMR (CDCl3) 0.9-1.0 (m, 16H), 2.2-2.5 (m, 4H), 7.6-7.9 (m, 3H)
TG 16 (3 μmol) 8.4 (10 μmol) 2.7 (30 μmol)
SOCE 20 (10 μmol) 40 (30 μmol) 50 (100 μmol)
IICR 44 (10 μmol) 58 (30 μmol) 79 (100 μmol)
NMR (CDCl3) 0.6-1.2 (m, 16H), 2.69 (m, 2H), 3.08 (m, 2H), 4.22 (m, 2H), 7.1-7.5 (m, 2H)
TG 24 (3 μmol) 11 (10 μmol) 13 (30 μmol)
SOCE 20 (10 μmol) 40 (30 μmol) 50 (100 μmol)
IICR 48 (10 μmol) 81 (30 μmol) 78 (100 μmol)
The aforementioned compounds of the present invention have transglutaminase-inhibiting activity or protein-crosslinking-inhibiting activity and further have intracellular calcium modulatory activity. Therefore, the compounds can be used for prevention or treatment of protein-crosslinking causative diseases and diseases associated with an increase in intracellular calcium concentration.
All publications, patents, and patent applications cited herein are incorporated herein by reference in their entirety.
| Number | Date | Country | Kind |
|---|---|---|---|
| 2009-255518 | Nov 2009 | JP | national |
| Filing Document | Filing Date | Country | Kind | 371c Date |
|---|---|---|---|---|
| PCT/JP2010/058411 | 5/19/2010 | WO | 00 | 7/20/2012 |
