Azo dyes from unsubstituted or substituted 3-amino-pyridine and aryl or heterocyclic couplers

DESCRIPTION
This invention concerns azo dyes having the general formula ##STR2## in which each of X, Y and Z are independently selected from H and a variety of substituents defined below, preferably provided that at least one of X and Y is a substituent selected, for example, from --CN, halogen, alkyl, and alkylsulfonyl, and C is the residue of a phenol, naphthol, indole, imidazothiazole, pyrazolone, thiazole, isothiazole or pyrazole type disperse dye coupling component. These dyes which are unexpectedly non-phototropic produce yellow to orange shades on hydrophobic fibers and exhibit improvements in one or more properties such as dyeability, dye exhaustion rate, light fastness, nonblooming, pH stability, build, fastness to ozone and nitrogen oxide, crock and wash fastness, migration, transfer, and pH stability on polyester, polyamide and other fibers including cellulose ester, over such dyes as are disclosed in British Patent No. 1,497,095.
The couplers C useful in the present invention have the formulae ##STR3## wherein: for couplers I through V as appropriate, R.sup.2 and R.sup.14 each represents hydrogen or up to three substituents selected from fluorine, chlorine, bromine, alkyl, cycloalkyl, alkoxy, phenoxy, alkylthio, arylthio, and radicals having the formula --NH--X--R.sup.3 in which X is --CO--, --COO--, or --SO.sub.2 and R.sup.3 is selected from alkyl and alkyl substituted with halogen, hydroxy, phenoxy, aryl, cyano, cycloalkyl, alkylsulfonyl, alkylthio, alkanoyloxy, and alkoxy, and when X is --CO-- in the formula --NH--X--R.sup.3, R.sup.3 also is selected from hydrogen, amino, alkylamino, dialkylamino, arylamino, aryl, and furyl;
R.sup.4 is selected from hydrogen, alkyl, aryl, and cycloalkyl;
R.sup.9, R.sup.10 and R.sup.11 are each selected from hydrogen, alkyl, phenyl, phenyl substituted with 1-3 substituents selected from Cl, Br, alkyl and alkoxy, alkylthio, benzylthio, cyclohexylthio, phenylthio and phenylthio substituted as for the phenyl;
e is 1 or 2;
each of the aliphatic portions or moieties of the above alkyl, cycloaliphatic, alkoxy, alkanoyl and like groups, as well as the aryl and aryloxy groups, may be substituted further with 1-3 of the following: hydroxy; halogen; cyano; succinimido; glutarimido; phthalimido; 2-pyrrolidono; cyclohexyl; phenyl; phenyl substituted with alkyl, alkoxy, halogen, alkanoylamino, cyano or alkoxycarbonyl; alkanoylamino; sulfamoyl; alkylsulfamoyl; vinylsulfonyl; acrylamido; phthalimidinyl; benzoylsulfonicimidyl; alkylsulfonamido; phenylsulfonamido; alkoxycarbonylamino; alkylcarbamoyloxy; alkoxycarbonyl; alkoxycarbonyloxy; ##STR4## wherein Y is --NH--, --NH--alkyl--, --O--, --S--, or --CH.sub.2 O--; --S--R.sup.6 wherein R.sup.6 is alkyl, phenyl, phenyl substituted with halogen, alkyl, alkoxy, alkanoylamino, cyano, or alkoxycarbonyl, pyridyl, pyrimidinyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, or ##STR5## --OXR.sup.3 ; --NH--X--R.sup.3 ; --X--R.sup.3 ; --CONR.sup.7 R.sup.7 ; --SO.sub.2 NR.sup.7 R.sup.7 ; wherein R.sup.3 and X are as defined above and each R.sup.7 is selected from H and R.sup.3 ; alkoxy; alkoxy substituted with 1-3 of hydroxy, cyano, alkanoyloxy, or alkoxy; phenoxy; phenoxy substituted with 1-3 of alkyl, alkoxy or halogen;
for Couplers VI, VII and VIII,
R.sup.1 and R.sup.2 each is H, alkyl, cyclohexyl, alkyl substituted cyclohexyl, aryl or alkyl substituted with aryl;
R.sup.3 is H, alkyl, lower alkyl substituted with 1-3 of halogen, hydroxy, aryl or lower alkanoyloxy, cyclohexyl, lower alkyl substituted cyclohexyl, or allyl; and
R.sup.2 and R.sup.3 collectively are pentamethylene or ethyleneoxyethylene;
in which each aryl group is phenyl or phenyl substituted with 1-3 of alkyl, hydroxyalkyl, alkoxy, hydroxy, halogen, cyclohexoxy, cyclohexylmethyl, alkanoylamino, nitro or alkoxycarbonyl;
X, Y, and Z of the pyridine ring are independently selected from hydrogen, halogen, alkyl, alkoxy, aryl, cyano, carbamoyl, CONHR.sub.12, CONR.sub.12 R.sub.13, SO.sub.2 R.sub.12, COOR.sub.12, sulfamoyl, SO.sub.2 NHR.sub.12, SO.sub.2 NR.sub.12 R.sub.13, formyl, nitro, SCN, and SR.sub.14, wherein R.sub.12 is alkyl, cycloalkyl, or aryl, each of which cycloalkyl and aryl R.sub.12 groups may be substituted with --CN, alkoxy, alkyl, hydroxy, alkanoyl or alkanoyloxy, R.sub.13 is alkyl which may be substituted with cycloalkyl, or aryl, each of which substituents on R.sub.13 may itself be substituted with --CN, alkoxy, alkyl, hydroxy, alkanoyl or alkanoyloxy, and R.sub.14 is selected from R.sub.12 and heterocyclic radicals, preferably ##STR6## pyridyl, pyrimidinyl, and 1,3,4-thiadiazol-2-yl, wherein R.sup.7 is as defined above, and preferably at least one of X and Y is cyano, SO.sub.2 R.sub.12, SR.sub.14, halogen, carbalkoxy, formyl, or nitro;
and wherein all of the aliphatic portions or moieties of all of the above groups within the definitions of X, Y, Z and the couplers, e.g the alkyl portions of alkoxy and alkylamino, contain from 1-8 carbons and are straight or branched.
Preferred dyes of the present invention have the formula ##STR7## wherein X is chlorine, bromine, cyano, alkylthio, alkylsulfonyl, arylsulfonyl or --S heterocycle; C is selected from ##STR8## wherein the ring is substituted in the 4 position with alkyl, alkoxy or halogen; ##STR9## wherein the naphthalene ring is unsubstituted; ##STR10## wherein R.sup.9 is alkyl or aryl, R.sup.4 is hydrogen, alkyl or cyanoethyl, and the benzene ring is unsubstituted; ##STR11## wherein R.sup.9 is phenyl, and R.sup.10 is hydrogen or methyl; ##STR12## wherein R.sup.4 is hydrogen or alkyl and R.sup.11 is alkyl or phenyl; ##STR13## wherein R.sup.1 is phenyl, R.sup.2 is hydrogen or alkyl and R.sup.3 is alkyl or aryl, ##STR14## wherein R.sup.1 is alkyl; and ##STR15## wherein R.sup.1 is alkyl and R.sup.2 is hydrogen or alkyl.
Most preferred dyes of the present invention have the formula ##STR16##
This invention will be further illustrated by the following examples although it will be understood that these examples are included merely for purposes of illustration and are not intended to limit the scope of the invention.
In general, the dyes are prepared by diazotizing 3-aminopyridines and then coupling, however, certain dyes are best prepared by nucleophilic substitution on the corresponding halopyridylazo dyes I as follows: ##STR17##
For example, Dyes I may be reacted with cuprous cyanide or sodium dicyanocuprate to produce the 2-cyano derivatives (II). Alkali metal mercaptides and sulfinates react with dyes I to give sulfides (III) and sulfones (IV), respectively. Displacements are also possible with nitrites, alkoxides, phenoxides, and sulfites to produce dyes containing nitro, alkoxy, phenoxy, and sulfo groups, respectively.
For each of the above reactions the temperature may vary within a wide range depending on the nature of the organic medium and, in particular, on the heat stability of the starting dyestuff. In general, the temperature should be maintained between about 25.degree. and 150.degree. C., with between 25.degree. and 100.degree. C. being preferred. Suitable solvents which may be readily selected by one skilled in the art include, for example, dimethylsulfoxide, formamide, dimethylformamide, dimethylacetamide, N-methyl-pyrrolidone, pyridine, quinoline, acetonitrile, benzonitrile and phosphoric acidtrisdimethylamide. Catalysts such as cupropus bromide and the like, also well known to the art, may be employed. The dye reactant may be the --Cl, --Br, --I or --F intermediate, and the displaced halogen in each of these reactions may be taken up by a cation, e.g., Na.sup.+, K.sup.+, or the like which may be present in a reactant, e.g., NaCu(CN).sub.2, or added thereto, such as K.sub.2 CO.sub.3 or sodium acetate, in sufficient amount to maintain the desired neutral or basic reaction system. Typical sulfinic compounds are CH.sub.3 SO.sub.2 Na, PhSO.sub.2 Na and typical mercaptans are C.sub.2 H.sub.5 -SH and Ph-SH. These reactants, of course, have the respective general formulae R.sub.12 SO.sub.2 M where, e.g., M is Na.sup.+, K.sup.+, or the like, and HSR.sub.14 where R.sub.12 and R.sub.14 are defined above.
The practice of the invention is illustrated further by the following examples:

EXAMPLES 1-10
Diazotization and Coupling of 3-Aminopyridine
3-Aminopyridine (0.1 m) is dissolved in 100 ml. of water containing 30 ml. concentrated HCl. The solution is cooled and a solution of 7.1 g. of NaNO.sub.2 in 20 ml. of water is added at 0.degree.-5.degree. C. After stirring for about 15 minutes, the diazonium salt is coupled with the following couplers:
Example 1-2-Phenylindole;
Example 2-N-Methyl-2-phenylindole;
Example 3-N-2-Carbamylethyl-2-phenylindole;
Example 4-6-Phenylimidazo[2,1-b]thiazole;
Example 5-2-(N,N-Diethylamino)-4-phenylthiazole;
Example 6-2-(N-Methyl-N-phenylamino)-4-phenylthiazole;
Example 7-5-Amino-3-methylisothiazole;
Example 8-5-Amino-3-t-butylpyrazole;
Example 9-5-Amino-3-methyl-N-phenylpyrazole; and
Example 10-5-Amino-3-methyl-N-2-hydroxyethylpyrazole.
The coupling is done as follows: Each of the above couplers (0.01 mole) is dissolved in 25-50 ml. of 1:5 acid (1 part propionic acid:5 parts acetic acid). To the chilled solution of each coupler is added a 0.01 mole aliquot of the above diazonium solution. The mineral acid is neutralized by the addition of solid ammonium acetate. Water is added to precipitate the dyes which are collected by filtration, washed with water and dried in air. If needed, the dyes are purified by reslurrying in hot methanol or ethanol.
EXAMPLES 11-20
Diazotization and Coupling of 3-Amino-2-chloropyridine
3-Amino-2-chloropyridine (12.8 g, 0.1 mole) is dissolved in 100 ml. H.sub.2 O and 30 ml. of concentrated HCl. The solution is cooled and a solution of 7.1 g. of NaNO.sub.2 in 20 ml. of H.sub.2 O is added at 0.degree.-5.degree. C. After being stirred at 0.degree.-5.degree. C. for 15 minutes, the diazonium salt was coupled to the following couplers:
Example 11-p-Cresol;
Example 12-2-Naphthol;
Example 13-m-Acetamidophenol;
Example 14-N-n-Butyl-3-hydroxy-2-naphthoicacid amide;
Example 15-3-Methyl-N-phenyl-5-pyrazolone;
Example 16-3,5-Diphenyl-5-pyrazolone;
Example 17-3-Methyl-5-pyrazolone;
The above couplers (0.01 m. of each) are dissolved in 25 ml. of water containing 1.6 g. of sodium hydroxide at room temperature. Ice is added thereto and then a 0.01 m. aliquot of the above diazonium salt. The pH is adjusted to about seven by addition of acetic acid. The dyes are collected by filtration, washed with water, and dried in air.
Dyeing of fiber material, according to the invention, is appropriately carried out from an aqueous suspension in the presence of carriers at between 80.degree. and 100.degree. C., in the absence of carriers between 100.degree.-130.degree. C., or using the so-called thermofixing process at 180.degree.-230.degree. C. Printing of textile materials can be carried out by steaming the goods, printed with the present dyes in the presence of a carrier at temperatures between 80.degree. and 110.degree. C. or in the absence of a carrier at 110.degree.-140.degree. C., or also by treating the printed goods according to said thermofixing process.
A typical general procedure by which polyester, e.g., poly(ethylene terephthalate) can be dyed with the present dyes is as follows: The dye cake is dispersed by heating and agitating a dyepot containing the dye cake and methyl Cellosolve. When the dyecake has been ground free of lumps and dissolved as much as possible in the methyl Cellosolve, 2% based on weight of the fabric of Igepon T-51 and 2.0% based on weight of the fabric of sodium lignin sulfonate from a premixed solution of the two components is added. Sufficient demineralized water is added to make about a 30:1 bath ratio of water to dye and a small amount of Versene 100 (sodium salt of ethylenediaminetetracetic acid) and Tanalon JDM-72 (dye carrier) are added. The pH of the dyebath is adjusted to about 5.0 with acetic acid. The fabric samples (wet-out) are entered into the dyepot and the entire contents thereof entered into a pressure dyeing container. The container is sealed and entered into a High Temperature Launder-Ometer which is heated to 49.degree. C. and rotation thereof started. The temperature of the Launder-Ometer is raised to 129.degree. C. at the rate of about 2.8.degree. C. per minute, and maintained at this temperature for 1 hour. The Launder-Ometer is then cooled, and the fabric samples removed and scoured in demineralized water containing 1 g./l. of neutral soapand 1 g./l. of sodium carbonate. The samples are rinsed in cold demineralized water and dried at 121.degree. C. in a forced air oven.
The following tables show additional exemplary dyes of the present invention.
TABLE 1__________________________________________________________________________ ##STR18##X Y Z R.sup.9 R.sup.2 R.sup.4__________________________________________________________________________H H H C.sub.6 H.sub.5 H CH.sub.3CH.sub.3 H H CH.sub.3 6-CH.sub.3 CH.sub.3CN H H CH.sub.3 6-CH.sub.3 C.sub.6 H.sub.5SCH.sub.3 Cl H CH.sub.3 H C.sub.2 H.sub.5CN H H C.sub.6 H.sub.5 H HCN Br H C.sub.6 H.sub.5 H CH.sub.3Cl NO.sub.2 4-Br CH.sub.3 H CH.sub.3Br CHO 4-Br CH.sub.3 5-OC.sub.2 H.sub.5 CH.sub.3SO.sub.2 CH.sub.3 CN 5-SO.sub.2 CH.sub.3 CH.sub.3 5-OC.sub.2 H.sub.5 HSO.sub.2 CH.sub.3 H 4-SO.sub.2 CH.sub.3 C.sub.6 H.sub.4p-Br H HSO.sub.2 CH.sub.3 H 4-SO.sub.2 CH.sub.3 C.sub.6 H.sub.5 H C.sub.2 H.sub.4 CONH.sub.2SO.sub.2 C.sub.6 H.sub.5 H H C.sub.6 H.sub.4p-OCH.sub.3 H C.sub.2 H.sub.4 CNSC.sub.2 H.sub.4 OH I H C.sub.6 H.sub.4p-OCH.sub.3 5-C.sub.6 H.sub.11 C.sub.2 H.sub.4 SO.sub.2 NH.sub.2SC.sub.6 H.sub.5 H 4-Cl C.sub.2 H.sub.4 CN 6-OC.sub.6 H.sub.5 C.sub.2 H.sub.4 N(COCH.sub.3).sub.2 6SO.sub.2 C.sub.6 H.sub.5 H 4-SO.sub.2 C.sub.6 H.sub.5 C.sub.2 H.sub.4 OCOCH.sub.3 6-SCH.sub.3 C.sub.2 H.sub.4 SO.sub.2 NHC.sub.2 H.sub.5CN SCH.sub.3 4-CN CH.sub.3 6-SC.sub.6 H.sub.5 C.sub.2 H.sub.4 SO.sub.2 NHC.sub.2 H.sub.5CH.sub.3 NO.sub.2 H CH.sub.3 6-NHCOOCH.sub.3 C.sub.2 H.sub.4 OHCN H H C.sub.3 H.sub.7 6-NHSO.sub.2 CH.sub.3 C.sub.2 H.sub.4 CNOCH.sub.3 SO.sub.2 CH.sub.3 H CH.sub.3 6-OCH.sub.3 C.sub.2 H.sub.4 OCOCH.sub.3SC.sub.6 H.sub.4m-CH.sub.3 SC.sub.6 H.sub.5 H CH.sub.3 5-NHCOCH.sub.3 C.sub.2 H.sub.4 OCOCH.sub.3CN H H C.sub.2 H.sub.5 6-NHCOCH.sub.2 Cl C.sub.6 H.sub.13C.sub.6 H.sub.5 SC.sub.6 H.sub.11 H C.sub.2 H.sub.5 6-NHCOC.sub.2 H.sub.4 C.sub.2 H.sub.4 OHCN H H C.sub.2 H.sub.5 6-NHCOC.sub.2 H.sub.4 CH.sub.2 C.sub.6 H.sub.5CN H 4-CN C.sub.2 H.sub. 5 6-NHCONHC.sub.2 H.sub.5 C.sub.2 H.sub.4 CNCONH.sub.2 CN 4-CN C.sub.6 H.sub.4p-OCH.sub.3 6-NHCON(C.sub.2 H.sub.5).sub.2 6 C.sub.2 H.sub.5CONHC.sub.2 H.sub.5 CN 4-CN C.sub.2 H.sub.5 6-CH.sub.3 C.sub.2 H.sub.4 NHCOCH.sub.3CON(C.sub.2 H.sub.5).sub.2 CN 4-CN C.sub.2 H.sub.5 6-NHCOCH.sub.3 C.sub.2 H.sub.4 CONH.sub.2CN H 4-CN CH.sub.3 H C.sub.2 H.sub.4 NHCOCH.sub.3CN SO.sub.2 CH.sub.3 4-CN CH.sub.3 H C.sub.2 H.sub.4 ClSO.sub.2 CH.sub.3 H 4-SO.sub.2 CH.sub.3 C.sub.6 H.sub.4p-CH.sub.3 6-OH C.sub.2 H.sub.4 ClSO.sub.2 N(CH.sub.3 ).sub.2 SO.sub.2 C.sub.6 H.sub.5 4-SO.sub.2 CH.sub.3 C.sub.6 H.sub.5 H HSO.sub.2 C.sub.4 H.sub.9n H 4-SO.sub.2 C.sub.4 H.sub.9n C.sub.6 H.sub.5 H HSC.sub.2 H.sub.4 OH H 4-SC.sub.2 H.sub.4 OH C.sub.6 H.sub.5 H HNO.sub.2 CO.sub.2 CH.sub.3 5-CO.sub.2 CH.sub.3 C.sub.6 H.sub.53 H HSCH.sub.3 CO.sub.2 C.sub.2 H.sub.5 5-CN C.sub.6 H.sub.5 H HCHO CO.sub.2 C.sub.2 H.sub.5 5-CN C.sub.6 H.sub.5 H HCOOCH.sub.3 H 4-OC.sub.2 H.sub.5 C.sub.6 H.sub.5 H CH.sub.3H CN 5-CN CH.sub.3 6-CH.sub.3 CH.sub.3SO.sub.2 C.sub.6 H.sub.5 H 4-SO.sub.2 C.sub.6 H.sub.5 CH.sub.3 6-CH.sub.3 C.sub.6 H.sub.5SO.sub.2 C.sub.6 H.sub.5 H 4-CH.sub.3 CH.sub.3 H C.sub.2 H.sub.5SO.sub.2 C.sub.6 H.sub.4p-Cl H 4-SO.sub.2 C.sub.6 H.sub.4p-Cl C.sub.6 H.sub.5 H HSO.sub.2 C.sub.6 H.sub.4p-CH.sub.3 H 4-SO.sub.2 C.sub.6 H.sub.4p-CH.sub.3 C.sub. 6 H.sub.5 H CH.sub.3SO.sub.2 C.sub.6 H.sub.4m-OCH.sub.3 SO.sub.2 C.sub.6 H.sub.11 4-SO.sub.2 C.sub.6 H.sub.4p-OCH.sub.3 CH.sub.3 H CH.sub.3SO.sub.2 CH.sub.2 CH.sub.2 CN H 4-SO.sub.2 CH.sub.2 CH.sub.2 CN CH.sub.3 5-OC.sub.2 H.sub.5 CH.sub.3SO.sub.2 CH.sub.2 C.sub.6 H.sub.5 H 4-SO.sub.2 CH.sub.2 C.sub.6 H.sub.5 CH.sub.3 5-OC.sub.2 H.sub.5 H ##STR19## s-pyridyl ##STR20## C.sub.6 H.sub.4p-Br H HSC.sub.6 H.sub.11 H 4-SC.sub.6 H.sub.11 C.sub.6 H.sub.5 H C.sub.2 H.sub.4 CONH.sub.2 ##STR21## NO.sub.2 H C.sub.6 H.sub.4p-OCH.sub.3 H C.sub.2 H.sub.4 CN ##STR22## s-pyrimidinyl H C.sub.6 H.sub.4p-OCH.sub.3 5-C.sub.6 H.sub.11 C.sub.2 H.sub.4 SO.sub.2 NH.sub.2 ##STR23## CN H C.sub.2 H.sub.4 CN 6-OC.sub.6 H.sub.5 C.sub.2 H.sub.4 N(COCH.sub.3).sub.2 . ##STR24## CN ##STR25## C.sub.2 H.sub.4 OCOCH.sub.3 6-SCH.sub.3 C.sub.2 H.sub.4 SO.sub.2 NHC.sub.2 H.sub.5 ##STR26## COOCH.sub.3 H CH.sub.3 6-SC.sub.6 H.sub.5 C.sub.2 H.sub.4 SO.sub.2 NHC.sub.2 H.sub.5 ##STR27## CN H CH.sub.3 6-NHCOOCH.sub.3 C.sub.2 H.sub.4 OH ##STR28## CN H C.sub.3 H.sub.7 6-NHSO.sub.2 CH.sub.3 C.sub.2 H.sub.4 CNNO.sub.2 H H CH.sub.3 6-OCH.sub.3 C.sub.2 H.sub.4 OCOCH.sub.3CN H 4-CN CH.sub.3 5-NHCOCH.sub.3 C.sub.2 H.sub.4 OCOCH.sub.3SO.sub.2 CH.sub.2 CH.sub.3 H 4-SO.sub.2 CH.sub.2 CH.sub.3 C.sub.2 H.sub.5 6-NHCOCH.sub.2 Cl C.sub.6 H.sub.13SO.sub.2 NHCH.sub.3 H 4-SO.sub.2 CH.sub.3 C.sub.2 H.sub.5 6-NHCOC.sub.2 H.sub.4 C.sub.2 H.sub.4 OHSO.sub.2 CH.sub.3 H 4-SO.sub.2 CH.sub.3 C.sub.2 H.sub.5 6-NHCOC.sub.2 H.sub.4 CH.sub.2 C.sub.6 H.sub.5SO.sub.2 C.sub.6 H.sub.5 H 4-SO.sub.2 C.sub.6 H.sub.5 C.sub.2 H.sub.5 6-NHCONHC.sub.2 H.sub.5 C.sub.2 H.sub.4 CNCN H 4-Cl C.sub.6 H.sub.4p-OCH.sub.3 6-NHCON(C.sub.2 H.sub.5).sub.2 C.sub.2 H.sub.5SCN NO.sub.2 4-Cl C.sub.2 H.sub.5 6-CH.sub.3 C.sub.2 H.sub.4 NHCOCH.sub.3CN H 4-Br C.sub.2 H.sub.5 6-NHCOCH.sub.3 C.sub.2 H.sub.4 CONH.sub.2s-pyridyl CHO 4-OCH.sub.3 CH.sub.3 H C.sub.2 H.sub.4 NHCOCH.sub.3CN H 4-CN CH.sub.3 H C.sub.2 H.sub.4 Cls-pyrimidinyl H 4-CN C.sub.6 H.sub.4p-CH.sub.3 6-OH C.sub.2 H.sub.4 ClCN CH.sub.3 4-CN C.sub.6 H.sub.5 H HCN Cl 4-CN C.sub.6 H.sub.5 H HCN H 4-CONH.sub.2 C.sub.6 H.sub.5 H HCN H 4-CON(C.sub.2 H.sub.5).sub.2 C.sub.6 H.sub.5 H HCN H 4-SO.sub.2 N(C.sub.2 H.sub.5).sub.2 C.sub.6 H.sub.5 H HCN H 4-SCN C.sub.6 H.sub.5 H HCN H 4-SCH.sub.3 C.sub.6 H.sub.5 H CH.sub.3SC.sub.6 H.sub.5 H 4-CN CH.sub.3 6-CH.sub.3 CH.sub.3SC.sub.4 H.sub.9n H 4-CN CH.sub.3 6-CH.sub.3 C.sub.6 H.sub.5CN C.sub.6 H.sub.5 4-CN CH.sub.3 H C.sub.2 H.sub.5CN CN 4-CN C.sub.6 H.sub.5 H HNO.sub.2 H H C.sub.6 H.sub.5 H CH.sub.3__________________________________________________________________________
TABLE 2__________________________________________________________________________ ##STR29##X Y Z R.sup.9 R.sup.10__________________________________________________________________________H H H C.sub.6 H.sub.5 HCH.sub.3 H H CH.sub.3 HCN H H CH.sub.3 HSCH.sub.3 Cl H CH.sub.3 C.sub.6 H.sub.5CN H H CH.sub.3 C.sub.6 H.sub.5CN Br H C.sub.6 H.sub.5 CH.sub.3Cl NO.sub.2 4-Br C.sub.6 H.sub.5 CH.sub.3Br CHO 4-Br C.sub.6 H.sub.5 CH.sub.3SO.sub.2 CH.sub.3 CN 5-SO.sub.2 CH.sub.3 CH.sub.3 HSO.sub.2 CH.sub.3 H 4-SO.sub.2 CH.sub.3 CH.sub.3 HSO.sub.2 CH.sub.3 H 4-SO.sub.2 CH.sub.3 C.sub.6 H.sub.4p-Br HSO.sub.2 C.sub.6 H.sub.5 H H C.sub.6 H.sub.4p-OCH.sub.3 HSC.sub.2 H.sub.4 OH I H C.sub.6 H.sub.4p-OCH.sub.3 BrSC.sub.6 H.sub.5 H 4-Cl C.sub.6 H.sub.4 CN BrSO.sub.2 C.sub.6 H.sub.5 H 4-SO.sub.2 C.sub.6 H.sub.5 C.sub.2 H.sub.4 OCOCH.sub.3 BrCN SCH.sub.3 4-CN CH.sub.3 C.sub.2 H.sub.5CH.sub.3 NO.sub.2 H CH.sub.3 C.sub.2 H.sub.5CN H H C.sub.3 H.sub.7 C.sub.6 H.sub.5OCH.sub.3 SO.sub.2 CH.sub.3 H CH.sub.3 C.sub.6 H.sub.5SC.sub.6 H.sub.4m-CH.sub.3 SC.sub.6 H.sub.5 H C.sub.2 H.sub.5 C.sub.6 H.sub.4p-CH.sub.3CN H H C.sub.2 H.sub.5 HC.sub.6 H.sub.5 SC.sub.6 H.sub.11 H C.sub.2 H.sub.5 CONHC.sub.2 H.sub.5CN H H C.sub.2 H.sub.5 CH.sub.3CN H 4-CN C.sub.6 H.sub.4p-OCH.sub.3 C.sub.2 H.sub.5CONH.sub.2 CN 4-CN C.sub.2 H.sub.5 SCNCONHC.sub.2 H.sub.5 CN 4-CN C.sub.2 H.sub. 5 CONH.sub.2CON(C.sub.2 H.sub.5).sub.2 CN 4-CN CH.sub.3 CH(CH.sub.3).sub.2CN H 4-CN CH.sub.3 C.sub.6 H.sub.5CN SO.sub.2 CH.sub.3 4-CN C.sub.6 H.sub.4p-CH.sub.3 C.sub.2 H.sub.5SO.sub.2 CH.sub.3 H 4-SO.sub.2 CH.sub.3 C.sub.6 H.sub.5 HSO.sub.2 N(CH.sub.3).sub.2 SO.sub.2 C.sub.6 H.sub.5 4-SO.sub.2 CH.sub.3 C.sub.6 H.sub.5 HSO.sub.2 C.sub.4 H.sub.9n H 4-SO.sub.2 C.sub.4 H.sub.9n C.sub.6 H.sub.5 HSC.sub.2 H.sub.4 OH H 4-SC.sub.2 H.sub.4 OH C.sub.6 H.sub.5 HNO.sub.2 CO.sub.2 CH.sub.3 5-CO.sub.2 CH.sub.3 C.sub.6 H.sub.5 HSCH.sub.3 CO.sub.2 C.sub.2 H.sub.5 5-CN C.sub.6 H.sub.5 HCHO CO.sub.2 C.sub.2 H.sub.5 5-CN C.sub.6 H.sub.5 HCOOCH.sub.3 H 4-OC.sub.2 H.sub.5 CH.sub.3 HH CN 5-CN CH.sub.3 HSO.sub.2 C.sub.6 H.sub.5 H 4-SO.sub.2 C.sub.6 H.sub.5 CH.sub.3 C.sub.6 H.sub.5SO.sub.2 C.sub.6 H.sub.5 H 4-CH.sub.3 CH.sub.3 C.sub.6 H.sub. 5SO.sub.2 C.sub.6 H.sub.4p-Cl H 4-SO.sub.2 C.sub.6 H.sub.4p-Cl C.sub.6 H.sub.5 CH.sub.3SO.sub.2 C.sub.6 H.sub.4p-CH.sub.3 H 4-SO.sub.2 C.sub.6 H.sub.4p-CH.sub.3 C.sub.6 H.sub.5 CH.sub.3SO.sub.2 C.sub.6 H.sub.4m-OCH.sub.3 SO.sub.2 C.sub.6 H.sub.11 4-SO.sub.2 C.sub.6 H.sub.4p-OCH.sub.3 C.sub.6 H.sub.5 CH.sub.3SO.sub.2 CH.sub.2 CH.sub.2 CN H 4-SO.sub.2 CH.sub.2 CH.sub.2 CN CH.sub.3 HSO.sub.2 CH.sub.2 C.sub.6 H.sub.5 H 4-SO.sub.2 CH.sub.2 C.sub.6 H.sub.5 CH.sub.3 H ##STR30## s-pyridyl ##STR31## C.sub.6 H.sub.4p-Br HSC.sub.6 H.sub.11 H 4-SC.sub.6 H.sub.11 C.sub.6 H.sub.4p-OCH.sub.3 H ##STR32## NO.sub.2 H C.sub.6 H.sub.4p-OCH.sub.3 Br ##STR33## s-pyrimidinyl H C.sub.6 H.sub.4 CN Br ##STR34## CN H C.sub.2 H.sub.4 OCOCH.sub.3 Br ##STR35## CN ##STR36## CH.sub.3 C.sub.2 H.sub.5 ##STR37## COOCH.sub.3 H CH.sub.3 C.sub.2 H.sub.5 ##STR38## CN H C.sub.3 H.sub.7 C.sub.6 H.sub.5 ##STR39## CN H CH.sub.3 C.sub. 6 H.sub.5NO.sub.2 H H C.sub.2 H.sub.5 C.sub.6 H.sub.4p-CH.sub.3CN H 4-CN C.sub.2 H.sub.5 HSO.sub.2 CH.sub.2 CH.sub.3 H 4-SO.sub.2 CH.sub.2 CH.sub.3 C.sub.2 H.sub.5 CONHC.sub.2 H.sub.5SO.sub.2 NHCH.sub.3 H 4-SO.sub.2 CH.sub.3 C.sub.2 H.sub.5 CH.sub.3SO.sub.2 CH.sub.3 H 4-SO.sub.2 CH.sub.3 C.sub.6 H.sub.4p-OCH.sub.3 C.sub.2 H.sub.5SO.sub.2 C.sub.6 H.sub.5 H 4-SO.sub.2 C.sub.6 H.sub.5 C.sub.2 H.sub.5 SCNCN H 4-Cl C.sub.2 H.sub.5 CONH.sub.2SCN NO.sub.2 4-Cl CH.sub.3 CH(CH.sub.3).sub.2CN H 4-Br CH.sub.3 C.sub.6 H.sub.5s-pyridyl CHO 4-OCH.sub.3 C.sub.6 H.sub.4p-CH.sub.3 C.sub.2 H.sub.5CN H 4-CN C.sub.2 H.sub.5 Hs-pyrimidinyl H 4-CN C.sub.6 H.sub.5 HCN CH.sub.3 4-CN C.sub.6 H.sub.5 HCN Cl 4-CN C.sub.6 H.sub.5 HCN H 4-CONH.sub.2 C.sub.6 H.sub.5 HCN H 4-CON(C.sub.2 H.sub.5).sub.2 C.sub.6 H.sub.5 HCN H 4-SO.sub.2 N(C.sub.2 H.sub.5).sub.2 C.sub.6 H.sub.5 HCN H 4-SCN CH.sub.3 HCN H 4-SCH.sub.3 CH.sub.3 HSC.sub.6 H.sub.5 H 4-CN CH.sub.3 C.sub.6 H.sub.5SC.sub.4 H.sub.9n H 4-CN CH.sub.3 C.sub.6 H.sub.5CN C.sub.6 H.sub.5 4-CN C.sub.6 H.sub.5 CH.sub.3CN CN 4-CN C.sub.6 H.sub.5 CH.sub.3NO.sub.2 H H C.sub.6 H.sub.5 CH.sub.3__________________________________________________________________________
TABLE 3__________________________________________________________________________ ##STR40##X Y Z R.sup.4 R.sup.11__________________________________________________________________________H H H H CH.sub.3CH.sub.3 H H H C.sub.6 H.sub.4p-OCH.sub.3CN H H H CF.sub.3SCH.sub.3 Cl H H COOC.sub.2 H.sub.5CN H H H CONHC.sub.4 H.sub.9nCN Br H H C.sub.6 H.sub.5Cl NO.sub.2 4-Br C.sub.6 H.sub.5 C.sub.6 H.sub.4p-BrBr CHO 4-Br C.sub.6 H.sub.5 C(CH.sub.3).sub.3SO.sub.2 CH.sub.3 CN 5-SO.sub.2 CH.sub.3 C.sub.6 H.sub.5 C.sub.6 H.sub.11SO.sub.2 CH.sub.3 H 4-SO.sub.2 CH.sub.3 C.sub.6 H.sub.5 C.sub.6 H.sub.5SO.sub.2 CH.sub.3 H 4-SO.sub.2 CH.sub.3 C.sub.6 H.sub.5 SO.sub.2 CH.sub.3SO.sub.2 C.sub.6 H.sub.5 H H C.sub.2 H.sub.5 SO.sub.2 CH.sub.3SC.sub.2 H.sub.4 OH I H CH.sub.3 CO CH.sub.3SC.sub.6 H.sub.5 H 4-Cl C.sub.6 H.sub.5 CO CH.sub.3SO.sub.2 C.sub.6 H.sub.5 H 4-SO.sub.2 C.sub.6 H.sub.5 CH.sub.3 CONH.sub.2CN SCH.sub.3 4-CH C.sub.2 H.sub.4 OH C.sub.2 H.sub.5CH.sub.3 NO.sub.2 H C.sub.2 H.sub.4 CN C.sub.2 H.sub.5CN H H C.sub.2 H.sub.4 OCOCH.sub.3 C.sub.2 H.sub.5OCH.sub.3 SO.sub.2 CH.sub.3 H C.sub.6 H.sub.11 CF.sub.3SC.sub.6 H.sub.4m-CH.sub.3 SC.sub.6 H.sub.5 H C.sub.2 H.sub.4 OH C.sub.6 H.sub.4p-ClCN H H CH.sub.2 C.sub.6 H.sub.5 CONHC.sub.2 H.sub.5C.sub.6 H.sub.5 SC.sub.6 H.sub.11 H C.sub.2 H.sub.4 CN CH(CH.sub.3).sub.2CN H H C.sub.2 H.sub.5 CH(CH.sub.3).sub.2CN H 4-CN C.sub.2 H.sub.4 NHCOCH.sub.3 C.sub.2 H.sub.5CONH.sub.2 CN 4-CN C.sub.2 H.sub.4 CONH.sub.2 CH.sub.3CONHC.sub.2 H.sub.5 CN 4-CN C.sub.2 H.sub.4 NHCOCH.sub.3 C.sub.2 H.sub.5CON(C.sub.2 H.sub.5).sub.2 CN 4-CN C.sub.2 H.sub.4 NHCOCH.sub.3 C.sub.6 H.sub.5CN H 4-CN C.sub.6 H.sub.5 CH.sub.3CN SO.sub.2 CH.sub.3 4-CN C.sub.6 H.sub.5 CH.sub.3SO.sub.2 CH.sub.3 H 4-SO.sub.2 CH.sub.3 C.sub.6 H.sub.5 CH.sub.3SO.sub.2 N(CH.sub.3).sub.2 SO.sub.2 C.sub.6 H.sub.5 4-SO.sub.2 CH.sub.3 C.sub.6 H.sub.5 CH.sub.3SO.sub.2 C.sub.4 H.sub.9n H 4-SO.sub.2 C.sub.4 H.sub.9n C.sub.6 H.sub.5 CH.sub.3SC.sub.2 H.sub.4 OH H 4-SC.sub.2 H.sub.4 OH C.sub.6 H.sub.5 CH.sub.3NO.sub.2 CO.sub.2 CH.sub.3 5-CO.sub.2 CH.sub.3 H CH.sub.3SCH.sub.3 CO.sub.2 C.sub.2 H.sub.5 5-CN H C.sub.6 H.sub.4p-OCH.sub.3CHO CO.sub.2 C.sub.2 H.sub.5 5-CN H CF.sub.3COOCH.sub.3 H 4-OC.sub.2 H.sub.5 H COOC.sub.2 H.sub.5H CN 5-CN H CONHC.sub.4 H.sub.9nSO.sub.2 C.sub.6 H.sub.5 H 4-SO.sub.2 C.sub.6 H.sub.5 H C.sub.6 H.sub.5SO.sub.2 C.sub.6 H.sub.5 H 4-CH.sub.3 C.sub.6 H.sub.5 C.sub.6 H.sub.4p-BrSO.sub.2 C.sub.6 H.sub.4p-Cl H 4-SO.sub.2 C.sub.6 H.sub.4p-Cl C.sub.6 H.sub.5 C(CH.sub.3).sub.3SO.sub.2 C.sub.6 H.sub.4p-CH.sub.3 H 4-SO.sub.2 C.sub.6 H.sub.4p-CH.sub.3 C.sub.6 H.sub.5 C.sub.6 H.sub.11SO.sub.2 C.sub.6 H.sub.4m-OCH.sub.3 SO.sub.2 C.sub.6 H.sub.11 4-SO.sub.2 C.sub.6 H.sub.4p-OCH.sub.3 C.sub.6 H.sub.5 C.sub.6 H.sub.5SO.sub.2 CH.sub.2 CH.sub.2 CN H 4-SO.sub.2 CH.sub.2 CH.sub.2 CN C.sub.6 H.sub.5 SO.sub.2 CH.sub.3SO.sub.2 CH.sub.2 C.sub.6 H.sub.5 H 4-SO.sub.2 CH.sub.2 C.sub.6 H.sub.5 C.sub.2 H.sub.5 SO.sub.2 CH.sub.3 ##STR41## s-pyridyl ##STR42## CH.sub.3 CO CH.sub.3SC.sub.6 H.sub. 11 H 4-SC.sub.6 H.sub.11 C.sub.6 H.sub.5 CO CH.sub.3 ##STR43## NO.sub.2 H CH.sub.3 CONH.sub.2 ##STR44## s-pyrimidinyl H C.sub.2 H.sub.4 OH C.sub.2 H.sub.5 ##STR45## CN H C.sub.2 H.sub.4 CN C.sub.2 H.sub.5 ##STR46## CN ##STR47## C.sub.2 H.sub.4 OCOCH.sub.3 C.sub.2 H.sub.5 ##STR48## COOCH.sub.3 H C.sub.6 H.sub.11 CF.sub.3 ##STR49## CN H C.sub.2 H.sub.4 OH C.sub.6 H.sub.4p-Cl ##STR50## CN H CH.sub.2 C.sub.6 H.sub.5 CONHC.sub.2 H.sub.5NO.sub.2 H H C.sub.2 H.sub.4 CN CH(CH.sub.3).sub.2CN H 4-CN C.sub.2 H.sub.5 CH(CH.sub.3).sub.2SO.sub.2 CH.sub.2 CH.sub.3 H 4-SO.sub.2 CH.sub.2 CH.sub.3 C.sub.2 H.sub.4 NHCOCH.sub.3 C.sub.2 H.sub.5SO.sub.2 NHCH.sub.3 H 4-SO.sub.2 CH.sub.3 C.sub.2 H.sub.4 CONH.sub.2 CH.sub.3SO.sub.2 CH.sub.3 H 4-SO.sub.2 CH.sub.3 C.sub.2 H.sub.4 NHCOCH.sub.3 C.sub.2 H.sub.5SO.sub.2 C.sub.6 H.sub.5 H 4-SO.sub.2 C.sub.6 H.sub.5 C.sub.2 H.sub.4 NHCOCH.sub.3 C.sub.6 H.sub.5CN H 4-Cl C.sub.6 H.sub.5 CH.sub.3SCN NO.sub.2 4-Cl C.sub.6 H.sub.5 CH.sub.3CN H 4-Br C.sub. 6 H.sub.5 CH.sub.3s-pyridyl CHO 4-OCH.sub.3 C.sub.6 H.sub.5 CH.sub.3CN H 4-CN C.sub.6 H.sub.5 CH.sub.3s-pyrimidinyl H 4-CN C.sub.6 H.sub.5 CH.sub.3CN CH.sub.3 4-CN H CH.sub.3CN Cl 4-CN H C.sub.6 H.sub.4p-OCH.sub.3CN H 4-CONH.sub.2 H CF.sub.3CN H 4-CON(C.sub.2 H.sub.5).sub.2 H COOC.sub.2 H.sub.5CN H 4-SO.sub.2 N(C.sub.2 H.sub.5).sub.2 H CONHC.sub.4 H.sub.9nCN H 4-SCN H C.sub.6 H.sub.5CN H 4-SCH.sub.3 C.sub.6 H.sub.5 C.sub.6 H.sub.4p-BrSC.sub.6 H.sub.5 H 4-CN C.sub.6 H.sub.5 C(CH.sub.3).sub.3SC.sub.4 H.sub.9n H 4-CN C.sub.6 H.sub.5 C.sub.6 H.sub.11CN C.sub.6 H.sub.5 4-CN C.sub.6 H.sub.5 C.sub.6 H.sub.5CN CN 4-CN C.sub.6 H.sub.5 SO.sub.2 CH.sub.3NO.sub.2 H H C.sub.2 H.sub.5 SO.sub.2 CH.sub.3__________________________________________________________________________
TABLE 4__________________________________________________________________________ ##STR51## OHX Y Z Position R.sup.2__________________________________________________________________________H H H 2 5-CH.sub.3CN H H 2 5-CH.sub.3CN H H 2 5-OCH.sub.3SCH.sub.3 Cl H 2 5-ClCN H H 2 5-ClCN Br H 4 3-OCH.sub.3Cl NO.sub.2 4-Br 4 3-OCH.sub.3Br CHO 4-Br 3,4 HSO.sub.2 CH.sub.3 CN 5-SO.sub.2 CH.sub.3 4 2-NHC.sub.6 H.sub.5SO.sub.2 CH.sub.3 H 4-SO.sub.2 CH.sub.3 2 5-NHCOCH.sub.3SO.sub.2 CH.sub.3 H 4-SO.sub.2 CH.sub.3 3,4 HSO.sub.2 C.sub.6 H.sub.5 H H 2 5-CONHC.sub.4 H.sub.9nSC.sub.2 H.sub.4 OH I H 2 5-C.sub.6 H.sub.11SC.sub. 6 H.sub.5 H 4-Cl 2 5-OC.sub.6 H.sub.5SO.sub.2 C.sub.6 H.sub.5 H 4-SO.sub.2 C.sub.6 H.sub.5 2 5-SCH.sub.3CN SCH.sub.3 4-CN 2 5-SC.sub.6 H.sub.5CH.sub.3 NO.sub.2 H 2 5-NHCOOCH.sub.3CN H H 2 5-NHSO.sub.2 CH.sub.3OCH.sub.3 SO.sub.2 CH.sub.3 H 2 5-NHCOCH.sub.3SC.sub.6 H.sub.4m-CH.sub.3 SC.sub.6 H.sub.5 H 2 5-NHCOCH.sub.2 ClCN H H 2 5-NHCOC.sub.2 H.sub.4 OHC.sub.6 H.sub.5 SC.sub.6 H.sub.11 H 2 5-ClCN H H 2 5-NHCONHC.sub.2 H.sub.5CN H 4-CN 2 5-NHCON(C.sub.2 H.sub.5).sub.2CONH.sub.2 CN 4-CN 2 5-CH.sub.3CONHC.sub.2 H.sub.5 CN 4-CN 2 5-NHCOCH.sub.3CON(C.sub.2 H.sub.5).sub.2 CN 4-CN 4 HCN H 4-CN 2 5-CH.sub.3CN SO.sub.2 CH.sub.3 4-CN 2 5-CH.sub.3SO.sub.2 CH.sub.3 H 4-SO.sub.2 CH.sub.3 2 5-OCH.sub.3SO.sub.2 N(CH.sub.3).sub.2 SO.sub.2 C.sub.6 H.sub.5 4-SO.sub.2 CH.sub.3 2 5-ClSO.sub.2 C.sub.4 H.sub.9n H 4-SO.sub.2 C.sub.4 H.sub.9n 2 5-ClSC.sub.2 H.sub.4 OH H 4-SC.sub.2 H.sub.4 OH 4 3-OCH.sub.3NO.sub.2 CO.sub.2 CH.sub.3 5-CO.sub.2 CH.sub.3 4 3-OCH.sub.3SCH.sub.3 CO.sub.2 C.sub.2 H.sub.5 5-CN 3,4 HCHO CO.sub.2 C.sub.2 H.sub.5 5-CN 4 2-NHC.sub.6 H.sub.5COOCH.sub.3 H 4-OC.sub.2 H.sub.5 2 5-NHCOCH.sub.3H CN 5-CN 3,4 HSO.sub.2 C.sub.6 H.sub.5 H 4-SO.sub.2 C.sub.6 H.sub.5 2 5-CONHC.sub.4 H.sub.9nSO.sub.2 C.sub.6 H.sub.5 H 4-CH.sub.3 2 5-C.sub.6 H.sub.11SO.sub.2 C.sub.6 H.sub.4p-Cl H 4-SO.sub.2 C.sub.6 H.sub.4p-Cl 2 5-OC.sub.6 H.sub.5SO.sub.2 C.sub.6 H.sub.4p-CH.sub.3 H 4-SO.sub.2 C.sub.6 H.sub.4p-CH.sub.3 2 5-SCH.sub.3SO.sub.2 C.sub.6 H.sub.4m-OCH.sub.3 SO.sub.2 C.sub.6 H.sub.11 4-SO.sub.2 C.sub.6 H.sub.4p-OCH.sub.3 2 5-SC.sub.6 H.sub.5SO.sub.2 CH.sub.2 CH.sub.2 CN H 4-SO.sub.2 CH.sub.2 CH.sub.2 CN 2 5-NHCOOCH.sub.3SO.sub.2 CH.sub.2 C.sub.6 H.sub.5 H 4-SO.sub.2 CH.sub.2 C.sub.6 H.sub.5 2 5-NHSO.sub.2 CH.sub.3 ##STR52## s-pyridyl ##STR53## 2 5-NHCOCH.sub.3SC.sub.6 H.sub.11 H 4-SC.sub.6 H.sub.11 2 5-NHCOCH.sub.2 Cl ##STR54## NO.sub.2 H 2 5-NHCOC.sub.2 H.sub.4 OH ##STR55## s-pyrimidinyl H 2 5-Cl ##STR56## CN H 2 5-NHCONHC.sub.2 H.sub.5 ##STR57## CN ##STR58## 2 5-NHCON(C.sub.2 H.sub.5).sub.2 ##STR59## COOCH.sub.3 H 2 5-CH.sub.3 ##STR60## CN H 2 5-NHCOCH.sub.3 ##STR61## CN H 4 HNO.sub.2 H H 2 5-CH.sub.3CN H 4-CN 2 5-CH.sub.3SO.sub.2 CH.sub.2 CH.sub.3 H 4-SO.sub.2 CH.sub.2 CH.sub.3 2 5-OCH.sub.3SO.sub.2 NHCH.sub.3 H 4-SO.sub.2 CH.sub.3 2 5-ClSO.sub.2 CH.sub.3 H 4-SO.sub.2 CH.sub.3 2 5-ClSO.sub.2 C.sub.6 H.sub.5 H 4-SO.sub.2 C.sub.6 H.sub.5 4 3-OCH.sub.3CN H 4-Cl 4 3-OCH.sub.3SCN NO.sub.2 4-Cl 3,4 HCN H 4-Br 4 2-NHC.sub.6 H.sub.5s-pyridyl CHO 4-OCH.sub.3 2 5-NHCOCH.sub.3CN H 4-CN 3,4 Hs-pyrimidinyl H 4-CN 2 5-CONHC.sub.4 H.sub.9nCN CH.sub.3 4-CN 2 5-C.sub.6 H.sub.11CN Cl 4-CN 2 5-OC.sub.6 H.sub.5CN H 4-CONH.sub.2 2 5-SCH.sub.3CN H 4-CON(C.sub.2 H.sub.5).sub.2 2 5-SC.sub.6 H.sub.5CN H 4-SO.sub.2 N(C.sub.2 H.sub.5).sub.2 2 5-NHCOOCH.sub.3CN H 4-SCN 2 5-NHSO.sub.2 CH.sub.3CN H 4-SCH.sub.3 2 5-NHCOCH.sub.3SC.sub.6 H.sub.5 H 4-CN 2 5-NHCOCH.sub.2 ClSC.sub.4 H.sub.9n H 4-CN 2 5-NHCOC.sub.2 H.sub.4 OHCN C.sub.6 H.sub.5 4-CN 2 5-ClCN CN 4-CN 2 5-NHCONHC.sub.2 H.sub.5NO.sub.2 H H 2 5-NHCON(C.sub.2 H.sub.5).sub.2__________________________________________________________________________
TABLE 5__________________________________________________________________________ ##STR62## OHX Y Z Position R.sup.2 R.sup.14__________________________________________________________________________H H H 2 H 6-SO.sub.2 N(CH.sub.3).sub.2CH.sub.3 H H 2 H 6-SO.sub.2 N(CH.sub.3).sub.2CN H H 2 3-CONH.sub.2 HSCH.sub.3 Cl H 4 H HCN H H 4 H HCN Br H 2,6 H HCl NO.sub.2 4-Br 2 H HBr CHO 4-Br 2 H 6-SO.sub.2 NHCH.sub.3SO.sub.2 CH.sub.3 CN 5-SO.sub.2 CH.sub.3 2 3-CONH.sub.2 HSO.sub.2 CH.sub.3 H 4-SO.sub.2 CH.sub.3 2 3-CONHC.sub. 6 H.sub.5 HSO.sub.2 CH.sub.3 H 4-SO.sub.2 CH.sub.3 2 3-CONHC.sub.6 H.sub.4p-OC.sub.2 H.sub.4 OH HSO.sub.2 C.sub.6 H.sub.5 H H 4 H HSC.sub.2 H.sub.4 OH I H 4 H HSC.sub.6 H.sub.5 H 4-Cl 4 H HSO.sub.2 C.sub.6 H.sub.5 H 4-SO.sub.2 C.sub.6 H.sub.5 2 H HCN SCH.sub.3 4-CN 2 H HCH.sub.3 NO.sub.2 H 2 3-CO.sub.2 CH.sub.3 HCN H H 2 3-CO.sub.2 CH.sub.3 HOCH.sub.3 SO.sub.2 CH.sub.3 H 2,4 H HSC.sub.6 H.sub.4m-CH.sub.3 SC.sub.6 H.sub.5 H 2 3-COCH.sub.2 Cl HCN H H 4 H HC.sub.6 H.sub.5 SC.sub.6 H.sub.11 H 4 H HCN H H 4 H HCN H 4-CN 4 H HCONH.sub.2 CN 4-CN 4 H HCONHC.sub.2 H.sub.5 CN 4-CN 2 3-CONHC.sub.6 H.sub.5 HCON(C.sub.2 H.sub.5).sub.2 CN 4-CN 2 H HCN H 4-CN 2 3-CONHC.sub.4 H.sub.9n HCN SO.sub.2 CH.sub. 3 4-CN 2 3-CONHC.sub.4 H.sub.9n HSO.sub.2 CH.sub.3 H 4-SO.sub.2 CH.sub.3 2 H 6-SO.sub.2 N(CH.sub.3).sub.2SO.sub.2 N(CH.sub.3).sub.2 SO.sub.2 C.sub.6 H.sub.5 4-SO.sub.2 CH.sub.3 2 H 6-SO.sub.2 N(CH.sub.3).sub.2SO.sub.2 C.sub.4 H.sub.9n H 4-SO.sub.2 C.sub.4 H.sub.9n 2 3-CONH.sub.2 HSC.sub.2 H.sub.4 OH H 4-SC.sub.2 H.sub.4 OH 4 H HNO.sub.2 CO.sub.2 CH.sub.3 5-CO.sub.2 CH.sub.3 4 H HSCH.sub.3 CO.sub.2 C.sub.2 H.sub.5 5-CN 2,6 H HCHO CO.sub.2 C.sub.2 H.sub.5 5-CN 2 H HCOOCH.sub.3 H 4-OC.sub.2 H.sub.5 2 H 6-SO.sub.2 NHCH.sub.3H CN 5-CN 2 3-CONH.sub.2 HSO.sub.2 C.sub.6 H.sub.5 H 4-SO.sub.2 C.sub.6 H.sub.5 2 3-CONHC.sub.6 H.sub.5 HSO.sub.2 C.sub.6 H.sub.5 H 4-CH.sub.3 2 3-CONHC.sub.6 H.sub.4p-OC.sub.2 H.sub.4 OH HSO.sub.2 C.sub.6 H.sub.4p-Cl H 4-SO.sub.2 C.sub.6 H.sub.4p-Cl 4 H HSO.sub. 2 C.sub.6 H.sub.4p-CH.sub.3 H 4-SO.sub.2 C.sub.6 H.sub.4p-CH.sub.3 4 H HSO.sub.2 C.sub.6 H.sub.4m-OCH.sub.3 SO.sub.2 C.sub.6 H.sub.11 4-SO.sub.2 C.sub.6 H.sub.4p-OCH.sub.3 4 H HSO.sub.2 CH.sub.2 CH.sub.2 CN H 4-SO.sub.2 CH.sub.2 CH.sub.2 CN 2 H HSO.sub.2 CH.sub.2 C.sub.6 H.sub.5 H 4-SO.sub.2 CH.sub.2 C.sub.6 H.sub.5 2 H H ##STR63## s-pyridyl ##STR64## 2 3-CO.sub.2 CH.sub.3 HSC.sub.6 H.sub.11 H 4-SC.sub.6 H.sub.11 2 3-CO.sub.2 CH.sub.3 H ##STR65## NO.sub.2 H 2,4 H H ##STR66## s-pyrimidinyl H 2 3-COCH.sub.2 Cl H ##STR67## CN H 4 H H ##STR68## CN ##STR69## 4 H H ##STR70## COOCH.sub.3 H 4 H H ##STR71## CN H 4 H H ##STR72## CN H 4 H HNO.sub.2 H H 2 3-CONHC.sub.6 H.sub.5 HCN H 4-CN 2 H HSO.sub.2 CH.sub.2 CH.sub.3 H 4-SO.sub.2 CH.sub.2 CH.sub.3 2 3-CONHC.sub.4 H.sub.9n HSO.sub.2 NHCH.sub.3 H 4-SO.sub.2 CH.sub.3 2 3-CONHC.sub.4 H.sub.9n HSO.sub.2 CH.sub.3 H 4-SO.sub.2 CH.sub.3 2 H 6-SO.sub.2 N(CH.sub.3).sub.2SO.sub.2 C.sub.6 H.sub.5 H 4-SO.sub.2 C.sub.6 H.sub.5 2 H 6-SO.sub.2 N(CH.sub.3).sub.2CN H 4-Cl 2 3-CONH.sub.2 HSCN NO.sub.2 4-Cl 4 H HCN H 4-Br 4 H Hs-pyridyl CHO 4-OCH.sub.3 2,6 H HCN H 4-CN 2 H Hs-pyrimidinyl H 4-CN 2 H 6-SO.sub.2 NHCH.sub.3CN CH.sub.3 4-CN 2 3-CONH.sub.2 HCN Cl 4-CN 2 3-CONHC.sub.6 H.sub.5 HCN H 4-CONH.sub.2 2 3-CONHC.sub.6 H.sub.4p-OC.sub.2 H.sub.4 OH HCN H 4-CON(C.sub.2 H.sub.5).sub.2 4 H HCN H 4-SO.sub.2 N(C.sub.2 H.sub.5).sub.2 4 H HCN H 4-SCN 4 H HCN H 4-SCH.sub.3 2 H HSC.sub.6 H.sub.5 H 4-CN 2 H HSC.sub.4 H.sub.9n H 4-CN 2 3-CO.sub.2 CH.sub.3 HCN C.sub.6 H.sub.5 4-CN 2 3-CO.sub.2 CH.sub.3 HCN CN 4-CN 2,4 H HNO.sub.2 H H 2 3-COCH.sub.2 Cl H__________________________________________________________________________
TABLE 6 ##STR73## X Y Z R.sup.1 R.sup.2 R.sup.3 H H H C.sub.6 H.sub.5 CH.sub.3 CH.sub.3 CH.sub.3 H H C.sub.6 H.sub.4p-OCH.sub.3 CH.sub.3 CH.sub.3 CN H H C.sub.6 H.sub.5 C.sub.6 H.sub.5 C.sub. 2 H.sub.5 SCH.sub.3 Cl H C.sub.6 H.sub.5 C.sub.6 H.sub.5 CH.sub.3 CN H H C.sub.6 H.sub.4p-OCH.sub.3 C.sub.6 H.sub.5 CH.sub.3 CN Br H C.sub.6 H.sub.5 C.sub.6 H.sub.5 H Cl NO.sub.2 4-Br C.sub.6 H.sub.5 C.sub.6 H.sub.4p-OCH.sub.3 H Br CHO 4-Br C.sub.6 H.sub.4p-OCH.sub.3 CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.3 SO.sub.2 CH.sub.3 CN 5-SO.sub.2 CH.sub.3 C.sub.6 H.sub.5 CH(CH.sub.3)C.sub.2 H.sub.5 H SO.sub.2 CH.sub.3 H 4-SO.sub.2 CH.sub.3 C.sub.6 H.sub.5 C.sub.6 H.sub.11 HSO.sub.2 CH.sub.3 H 4-SO.sub.2 CH.sub.3 C.sub.6 H.sub.4p-CH.sub.3 C.sub.6 H.sub.11 C.sub.2 H.sub.5 SO.sub.2 C.sub.6 H.sub.5 H H C.sub.6 H.sub.4p-Cl CH.sub.3 CH.sub.3 SC.sub.2 H.sub.4 OH I H C.sub.6 H.sub.4m-Cl C.sub.6 H.sub.4p-NHCOCH.sub.3 CH.sub.3 SC.sub.6 H.sub.5 H 4-Cl C.sub.6 H.sub.4o-Cl C.sub.6 H.sub.4p-CH.sub.3 CH.sub.3 SO.sub. 2 C.sub.6 H.sub.5 H 4-SO.sub.2 C.sub.6 H.sub.5 C.sub.6 H.sub.4p-Br C.sub.6 H.sub.4m-CH.sub.3 CH.sub.3 CN SCH.sub.3 4-CN C.sub.6 H.sub.4p-NO.sub.2 C.sub.6 H.sub.4m-CH.sub.3 CH.sub.3 CH.sub.3 NO.sub.2 H C.sub.6 H.sub.11 CH.sub.3 CH.sub.3 CN H H CH.sub.2 C.sub.6 H.sub.5 CH.sub.3 CH.sub.3 OCH.sub.3 SO.sub.2 CH.sub.3 H CH.sub.3 C.sub.6 H.sub.5 C.sub.2 H.sub.5 SC.sub.6 H.sub.4m-CH.sub.3 SC.sub.6 H.sub.5 H C.sub.2 H.sub.5 C.sub.6 H.sub.5 C.sub.2 H.sub.5 CN H H C.sub.6 H.sub.5 C.sub.6 H.sub.5 CH.sub.2 CHCH.sub.2 C.sub.6 H.sub.5 SC.sub.6 H.sub.11 H C.sub.6 H.sub.5 C.sub.6 H.sub.5 CH.sub.2 CH.sub.2 OH CN H H C.sub.6 H.sub.5 CH.sub.2 CH.sub.2OCH.sub.2 CH.sub.2 CN H 4-CN C.sub.6 H.sub.5 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 CONH.sub.2 CN 4-CN C.sub.6 H.sub.5 CH.sub.2 C.sub.6 H.sub.5 C.sub.2 H.sub.5 CONHC.sub.2 H.sub.5 CN 4-CN C.sub.6 H.sub.4p-OCH.sub.3 C.sub.6 H.sub.5 C.sub.2 H.sub.5 CON(C.sub.2 H.sub.5).sub.2 CN 4-CN C.sub.6 H.sub.4p-OCH.sub.3 C.sub.6 H.sub.5 CH.sub.2 CH.sub.2 OOCCH.sub.3 CN H 4-CN C.sub.6 H.sub.4p-OCH.sub.3 C.sub.4 H.sub.9n C.sub.4 H.sub.9n CN SO.sub.2 CH.sub.3 4-CN C.sub.6 H.sub.4p-OCH.sub.3 C.sub.6 H.sub.11 H SO.sub.2 CH.sub.3 H 4-SO.sub.2 CH.sub.3 C.sub.6 H.sub.4p-OCH.sub.3 CH(CH.sub.3).sub.2 H SO.sub.2 N(CH.sub.3).sub.2 SO.sub.2 C.sub.6 H.sub.5 4-SO.sub.2 CH.sub.3 C.sub.6 H.sub.4p-OH C.sub.6 H.sub.5 C.sub.2 H.sub.5 SO.sub.2 C.sub.4 H.sub.9n H 4-SO.sub.2 C.sub.4 H.sub.9n C.sub.6 H.sub.4p-OH CH.sub.3 CH.sub.3 SC.sub.2 H.sub.4 OH H 4-SC.sub.2 H.sub.4 OH C.sub.6 H.sub.4p-OC.sub.2 H.sub.5 CH.sub.3 CH.sub.3 NO.sub.2 CO.sub.2 CH.sub.3 5-CO.sub.2 CH.sub.3 C.sub.6 H.sub.4p-OCH.sub.2 CH(CH.sub.3).sub.2 CH.sub.3 CH.sub.3 SCH.sub.3 CO.sub.2 C.sub.2 H.sub.5 5-CN C.sub.6 H.sub.4p-OC.sub.6 H.sub.11 CH.sub.3 CH.sub.3 CHO CO.sub.2 C.sub.2 H.sub.5 5-CN C.sub.6 H.sub.4p-CH.sub.2 C.sub.6 H.sub.11 CH.sub.3 CH.sub.3 COOCH.sub.3 H 4-OC.sub.2 H.sub.5 C.sub.6 H.sub.4p-CH.sub.3 C.sub.6 H.sub.5 H H CN 5-CN C.sub.6 H.sub.5 C.sub.6 H.sub.5o,p-di-CH.sub.3 H SO.sub.2 C.sub.6 H.sub.5 H 4-SO.sub.2 C.sub.6 H.sub.5 C.sub.6 H.sub.5 C.sub.6 H.sub.4o-Cl H SO.sub.2 C.sub.6 H.sub.5 H 4-CH.sub.3 C.sub.6 H.sub.5 C.sub.6 H.sub.3o,m-di-Cl H SO.sub.2 C.sub.6 H.sub.4p-Cl H 4-SO.sub.2 C.sub.6 H.sub.4p-Cl C.sub.6 H.sub.5 C.sub.6 H.sub.4p-Cl H SO.sub.2 C.sub.6 H.sub.4p-CH.sub.3 H 4-SO.sub.2 C.sub.6 H.sub.4p-CH.sub.3 C.sub.6 H.sub.5 C.sub.6 H.sub.4m-CH.sub.3 H SO.sub.2 C.sub.6 H.sub.4m-OCH.sub.3 SO.sub.2 C.sub.6 H.sub.11 4-SO.sub.2 C.sub.6 H.sub.4 p-OCH.sub.3 C.sub.6 H.sub.5 C.sub.6 H.sub.4o-OCH.sub.3 H SO.sub.2 CH.sub.2 CH.sub.2 CN H 4-SO.sub.2 CH.sub.2 CH.sub.2 CN C.sub.6 H.sub.4p-OCH.sub.3 C.sub.6 H.sub.4o-CH.sub.3 H SO.sub.2 CH.sub.2 C.sub.6 H.sub.5 H 4-SO.sub.2 CH.sub.2 C.sub.6 H.sub.5 C.sub.6 H.sub.4p-OCH.sub.3 C.sub.6 H.sub.4m-CH.sub.3 H ##STR74## s-pyridyl ##STR75## C.sub.6 H.sub.5 H CH.sub.2 CHCH.sub.2 SC.sub.6 H.sub.11 H 4-SC.sub.6 H.sub.11 C.sub.6 H.sub.4p-OCH.sub.3 C.sub.6 H.sub.5 C.sub.2 H.sub.5 ##STR76## NO.sub.2 H C.sub.6 H.sub.5 CH.sub.2 C.sub.6 H.sub.5 H ##STR77## s-pyrimidinyl H C.sub.6 H.sub.4p-OCH.sub. 3 C.sub.6 H.sub.5 C.sub.2 H.sub.5 ##STR78## CN H C.sub.6 H.sub.5 C.sub.6 H.sub.4p-CH.sub.3 CH.sub.3 ##STR79## CN ##STR80## C.sub.6 H.sub.5 CH.sub.2 CH.sub.2 C.sub.6 H.sub.5 H ##STR81## COOCH.sub.3 H C.sub.6 H.sub.5 CH.sub.3 H ##STR82## CN H C.sub.6 H.sub.5 C.sub.6 H.sub.4p-CH.sub.2 CH.sub.2 OH H ##STR83## CN H C.sub.6 H.sub.4p-NHCOCH.sub.3 C.sub.6 H.sub.5 C.sub.2 H.sub.5 NO.sub.2 H H C.sub.6 H.sub.5 C.sub.6 H.sub.4p-CH.sub.3 H CN H 4-CN C.sub.6 H.sub.5 C.sub.6 H.sub.4m-NHCOCH.sub.3 H SO.sub.2 CH.sub.2 CH.sub.3 H 4-SO.sub.2 CH.sub.2 CH.sub.3 C.sub.6 H.sub.5 C.sub.6 H.sub.4o-CH.sub.3 H SO.sub.2 NHCH.sub.3 H 4-SO.sub.2 CH.sub.3 C.sub.6 H.sub.5 C.sub.6 H.sub.4m-F H SO.sub.2 CH.sub.3 H 4-SO.sub.2 CH.sub.3 C.sub.6 H.sub.5 C.sub.6 H.sub.4m-CH.sub.3 C.sub.2 H.sub.5 SO.sub.2 C.sub.6 H.sub.5 H 4-SO.sub.2 C.sub.6 H.sub.5 C.sub.6 H.sub.5 C.sub.6 H.sub.4m-OCH.sub.3 H CN H 4-Cl C.sub.6 H.sub.5 CH.sub.2 C.sub.6 H.sub.5 C.sub.2 H.sub.5 SCN NO.sub.2 4-Cl C.sub.6 H.sub.5 CH.sub.3 CH.sub.3 CN H 4-Br C.sub.6 H.sub.4p-OCH.sub.3 CH.sub.3 CH.sub.3 s-pyridyl CHO 4-OCH.sub.3 C.sub.6 H.sub.5 C.sub.6 H.sub.5 C.sub.2 H.sub.5 CN H 4-CN C.sub.6 H.sub.5 C.sub.6 H.sub.5 CH.sub.3 s-pyrimidinyl H 4-CN C.sub.6 H.sub.4p-OCH.sub.3 C.sub.6 H.sub.5 CH.sub.3 CN CH.sub.3 4-CN C.sub.6 H.sub.5 C.sub.6 H.sub.5 H CN Cl 4-CN C.sub.6 H.sub.5 C.sub.6 H.sub.4p-OCH.sub.3 H CN H 4-CONH.sub.2 C.sub.6 H.sub.4p-OCH.sub.3 CH.sub.2 CH.sub.2 CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.3 CN H 4-CON(C.sub.2 H.sub.5).sub.2 C.sub.6 H.sub.5 CH(CH.sub.3)C.sub.2 H.sub.5 H CN H 4-SO.sub.2 N(C.sub.2 H.sub.5).sub.2 C.sub.6 H.sub.5 C.sub.6 H.sub.11 H CN H 4-SCN C.sub.6 H.sub.4p-CH.sub.3 C.sub.6 H.sub.11 C.sub.2 H.sub.5 CN H 4-SCH.sub.3 C.sub.6 H.sub.4p-Cl CH.sub.3 CH.sub.3 SC.sub.6 H.sub.5 H 4-CN C.sub.6 H.sub.4m-Cl C.sub.6 H.sub.4p-NHCOCH.sub.3 CH.sub.3 SC.sub.4 H.sub.9n H 4-CN C.sub.6 H.sub.4o-Cl C.sub.6 H.sub.4p-CH CH.sub.3 CN C.sub.6 H.sub.5 4-CN C.sub.6 H.sub.4p-Br C.sub.6 H.sub.4m-CH.sub.3 CH.sub.3 CN CN 4-CN C.sub.6 H.sub.4p-NO.sub.2 C.sub.6 H.sub.4m-CH.sub.3 CH.sub.3 NO.sub.2 H H C.sub.6 H.sub.11 CH.sub.3 CH.sub.3
TABLE 7__________________________________________________________________________ ##STR84##X Y Z R.sup.1 R.sup.2__________________________________________________________________________H H H CH.sub.3 HCH.sub.3 H H C.sub.4 H.sub.9n HCN H H C.sub.3 H.sub.7n CH.sub.3SCH.sub.3 Cl H C.sub.2 H.sub.5 C.sub.2 H.sub.5CN H H Ph C.sub.6 H.sub.11CN Br H OCH.sub.3 CH.sub.2 PhCl NO.sub.2 4-Br OC.sub.3 H.sub.7n CH.sub.2 CH.sub.2 OHBr CHO 4-Br H Php-ClSO.sub.2 CH.sub.3 CN 5-SO.sub.2 CH.sub.3 H Php-CH.sub.3SO.sub.2 CH.sub.3 H 4-SO.sub.2 CH.sub.3 CH.sub.3 Php-OCH.sub.3SO.sub.2 CH.sub.3 H 4-SO.sub.2 CH.sub.3 Ph Ph o,p-di-CH.sub.3SO.sub.2 C.sub.6 H.sub.5 H H CH.sub.3 HSC.sub.2 H.sub.4 OH I H C.sub.4 H.sub.9n HSC.sub.6 H.sub.5 H 4-Cl C.sub.3 H.sub.7n CH.sub.3SO.sub.2 C.sub.6 H.sub.5 H 4-SO.sub.2 C.sub.6 H.sub.5 C.sub.2 H.sub.5 C.sub.2 H.sub.5CN SCH.sub.3 4-CN Ph C.sub.6 H.sub.11CH.sub.3 NO.sub.2 H OCH.sub.3 CH.sub.2 PhCN H H OC.sub.3 H.sub.7n CH.sub.2 CH.sub.2 OHOCH.sub.3 SO.sub.2 CH.sub.3 H H Php-ClSC.sub.6 H.sub.4m-CH.sub.3 SC.sub.6 H.sub.5 H H Php-CH.sub.3CN H H CH.sub.3 Php-OCH.sub.3C.sub.6 H.sub.5 SC.sub.6 H.sub.11 H Ph Ph o,p-di-CH.sub.3CN H H CH.sub.3 HCN H 4-CN C.sub.4 H.sub.9n HCONH.sub.2 CN 4-CN C.sub.3 H.sub.7n CH.sub.3CONHC.sub.2 H.sub.5 CN 4-CN C.sub.2 H.sub.5 C.sub.2 H.sub.5CON(C.sub.2 H.sub.5).sub.2 CN 4-CN Ph C.sub.6 H.sub.11CN H 4-CN OCH.sub.3 CH.sub.2 PhCN SO.sub.2 CH.sub.3 4-CN OC.sub.3 H.sub.7n CH.sub.2 CH.sub.2 OHSO.sub.2 CH.sub.3 H 4-SO.sub.2 CH.sub.3 H Php-ClSO.sub.2 N(CH.sub.3).sub.2 SO.sub.2 C.sub.6 H.sub.5 4-SO.sub.2 CH.sub.3 H Php-CH.sub.3SO.sub.2 C.sub.4 H.sub.9n H 4-SO.sub.2 C.sub.4 H.sub.9n CH.sub.3 Php-OCH.sub.3SC.sub.2 H.sub.4 OH H 4-SC.sub.2 H.sub.4 OH Ph Pho,p-di-CH.sub. 3NO.sub.2 CO.sub.2 CH.sub.3 5-CO.sub.2 CH.sub.3 CH.sub.3 HSCH.sub.3 CO.sub.2 C.sub.2 H.sub.5 5-CN C.sub.4 H.sub.9n HCHO CO.sub.2 C.sub.2 H.sub.5 5-CN C.sub.3 H.sub.7n CH.sub.3COOCH.sub.3 H 4-OC.sub.2 H.sub.5 C.sub.2 H.sub.5 C.sub.2 H.sub.5H CN 5-CN Ph C.sub.6 H.sub.11SO.sub.2 C.sub.6 H.sub.5 H 4-SO.sub.2 C.sub.6 H.sub.5 OCH.sub.3 CH.sub.2 PhSO.sub.2 C.sub.6 H.sub.5 H 4-CH.sub.3 OC.sub.3 H.sub.7n CH.sub.2 CH.sub.2 OHSO.sub.2 C.sub.6 H.sub.4p-Cl H 4-SO.sub.2 C.sub.6 H.sub.4p-Cl H Php-ClSO.sub.2 C.sub.6 H.sub.4p-CH.sub.3 H 4-SO.sub.2 C.sub.6 H.sub.4p-CH.sub.3 H Php-CH.sub.3SO.sub.2 C.sub.6 H.sub.4m-OCH.sub.3 SO.sub.2 C.sub.6 H.sub.11 4-SO.sub.2 C.sub.6 H.sub.4m-OCH.sub.3 CH.sub.3 Php-OCH.sub.3SO.sub.2 CH.sub.2 CH.sub.2 CN H 4-SO.sub.2 CH.sub.2 CH.sub.2 CN Ph Pho,p-di-CH.sub. 3SO.sub.2 CH.sub.2 C.sub.6 H.sub.5 H 4-SO.sub.2 CH.sub.2 C.sub.6 H.sub.5 CH.sub.3 H ##STR85## s-pyridyl ##STR86## C.sub.4 H.sub.9n HSC.sub.6 H.sub.11 H 4-SC.sub.6 H.sub.11 C.sub.3 H.sub.7n CH.sub.3 ##STR87## NO.sub.2 H C.sub.2 H.sub.5 C.sub.2 H.sub.5 ##STR88## s-pyrimidinyl H Ph C.sub.6 H.sub.11 ##STR89## CN H OCH.sub.3 CH.sub.2 Ph ##STR90## CN ##STR91## OC.sub.3 H.sub.7n CH.sub.2 CH.sub.2 OH ##STR92## COOCH.sub.3 H H Php-Cl ##STR93## CN H H Php-CH.sub.3 ##STR94## CN H CH.sub.3 Php-OCH.sub.3NO.sub.2 H H Ph Pho,p-di-CH.sub. 3CN H 4-CN CH.sub.3 HSO.sub. 2 CH.sub.2 CH.sub.3 H 4-SO.sub.2 CH.sub.2 CH.sub.3 C.sub.4 H.sub.9n HSO.sub.2 NHCH.sub.3 H 4-SO.sub.2 CH.sub.3 C.sub.3 H.sub.7n CH.sub.3SO.sub.2 CH.sub.3 H 4-SO.sub.2 CH.sub.3 C.sub.2 H.sub.5 C.sub.2 H.sub.5SO.sub.2 C.sub.6 H.sub.5 H 4-SO.sub.2 C.sub.6 H.sub.5 Ph C.sub.6 H.sub.11CN H 4-Cl OCH.sub.3 CH.sub.2 PhSCN NO.sub.2 4-Cl OC.sub.3 H.sub.7n CH.sub.2 CH.sub.2 OHCN H 4-Br H Php-Cls-pyridyl CHO 4-OCH.sub.3 H Php-CH.sub.3CN H 4-CN CH.sub.3 Php-OCH.sub.3s-pyrimidinyl H 4-CN Ph Pho,p-di-CH.sub. 3CN CH.sub.3 4-CN CH.sub.3 HCN Cl 4-CN C.sub.4 H.sub.9n HCN H 4-CONH.sub.2 C.sub.3 H.sub.7n CH.sub.3CN H 4-CON(C.sub.2 H.sub.5).sub.2 C.sub.2 H.sub.5 C.sub.2 H.sub.5CN H 4-SO.sub.2 N(C.sub.2 H.sub.5).sub.2 Ph C.sub.6 H.sub.11CN H 4-SCN OCH.sub.3 CH.sub.2 PhCN H 4-SCH.sub.3 OC.sub.3 H.sub.7n CH.sub.2 CH.sub. 2 OHSC.sub.6 H.sub.5 H 4-CN H Php-ClSC.sub.4 H.sub.9n H 4-CN H Php-CH.sub.3CN C.sub.6 H.sub.5 4-CN CH.sub.3 Php-OCH.sub.3CN CN 4-CN Ph Pho,p-di-CH.sub. 3NO.sub.2 H H CH.sub.3 H__________________________________________________________________________
The invention has been described in detail with particular reference to preferred embodiments thereof, but it will be understood that variations and modifications will be effected within the spirit and scope of the invention.

Number	Name	Date
2294380	Braker	Sep 1942
2313738	Dickey et al.	Mar 1943
2857372	Straley et al.	Oct 1958
2864813	Bossard et al.	Dec 1958
3312681	Lewis	Apr 1967
3337290	Pons et al.	Aug 1967
4025301	Lang	May 1977
4301068	Giles et al.	Nov 1981
4302390	Giles et al.	Nov 1981
4358404	Chapman et al.	Nov 1982

Azo dyes from unsubstituted or substituted 3-amino-pyridine and aryl or heterocyclic couplers

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US Referenced Citations (10)

Non-Patent Literature Citations (2)

Entry
Ginsberg et al., Index Chemicus, vol. 23, 69675 (1966).
Guser et al., Index Chemicus, vol. 27, 86189 (1967).