Claims
- 1. A process to produce a compound of the formula ##STR95## wherein A is ##STR96## R.sub.1 is selected from the group consisting of hydrogen, lower alkyl, phenyl, alkoxy lower alkyl, pyridyl, and tolyl; R.sub.2 is selected from the group consisting of hydrogen or lower alkyl; R.sub.3 is selected from the group consisting of hydrogen or lower alkyl; R.sub.4 is selected from the group consisting of hydrogen, halogen, trifluoromethyl, lower alkyl, mono- or di- C.sub.1 to C.sub.7 alkyl or phenyl, chlorophenyl or tolyl substituted amino, amino, hydroxy lower alkyl and lower alkanoyl; R.sub.6 is selected from the group consisting of phenyl, mono-halo substituted phenyl, di-halo substituted phenyl, pyridyl and mono-halo substituted pyridyl; and ##STR97## is selected from the group consisting of ##STR98## which comprises the following steps in combination (a) reacting a compound of the formula ##STR99## wherein A is selected from the group consisting of ##STR100## wherein R.sub.3, R.sub.4, R.sub.6 and ##STR101## are as above; with a compound selected from the group consisting of alkali metal nitrites, alkyl nitrites or a nitrosyl chloride gaseous solution;
- (b) condensing either the product from (a) or a compound of the formula ##STR102## wherein A, ##STR103## R.sub.4, R.sub.3, R.sub.6 are as above with a nitroalkane anion of the formula R.sub.2 --CH--NO.sub.2 wherein R.sub.2 is selected from the group consisting of hydrogen or lower alkyl;
- (c) catalytically hydrogenating the product from (b) with H.sub.2 /Raney nickel or lithium aluminum hydride with limitation that A is not N-oxide;
- (d) acylating the product from (c) with an acid halide or an acid anhydride of the formulas R.sub.1 COX or (R.sub.1 CO).sub.2) respectively wherein R.sub.1 is as above;
- (e) cyclizing the product from (d) with a dehydrating agent selected from phosphorus pentoxide, polyphosphoric acid or an organic or inorganic acid;
- (f) dehydrogenating with manganese dioxide, palladium on carbon or potassium permanganate the cyclized product of (e) to produce the final product.
- 2. A process for producing a compound of the formula ##STR104## wherein A is ##STR105## R.sub.1 is selected from the group consisting of hydrogen, lower alkyl, phenyl, alkoxy lower alkyl, mono- or di-C.sub.1 to C.sub.7 alkyl or phenyl, chlorophenyl or tolyl substituted amino lower alkyl, pyridyl, and tolyl; R.sub.2 and R.sub.3 are selected from the group consisting of hydrogen, lower alkyl; R.sub.4 is selected from the group consisting of hydrogen, halogen, trifluoromethyl, lower alkyl, mono- or di-C.sub.1 to C.sub.7 alkyl or phenyl, chlorophenyl or tolyl substituted amino, amino, hydroxy lower alkyl and lower alkanoyl; R.sub.6 is selected from the group consisting of phenyl, mono-halo substituted phenyl, di-halo substituted phenyl, pyridyl and mono-halo substituted pyridyl; and ##STR106## is selected from the group consisting of ##STR107## which comprises the following steps in combination (a) reacting a compound of the formula ##STR108## wherein ##STR109## R.sub.3, R.sub.4 and Rhd 6 are as above and A is ##STR110## with a compound selected from the group consisting of alkali metal nitrites, alkyl nitrites or a nitrosyl chloride gaseous solution;
- (b) condensing the product from (a) with a nitroalkane of the formula R.sub.2 --CH.sub.2 NO.sub.2 wherein R.sub.2 is selected from the group consisting of hydrogen and lower alkyl;
- (c) catalytically hydrogenating the product from (b) with H.sub.2 /Raney nickel or lithuim aluminum hydride with limitation that A is not N-oxide;
- (d) acylating and spontaneously cyclizing the product from (c) with an acylating agent selected from the group consisting of orthoesters, esters, amidines, nitriles, orthoamides, ester imidates or a compound of the formula ##STR111## (e) dehydrogenating with manganese dioxide, palladium on carbon or potassium permanganate the cyclized product of (d) to produce the final product.
Parent Case Info
This is a division of application Ser. No. 905,820 filed May 15, 1978, now U.S. Pat. No. 4,280,957 which is a continuation of Ser. No. 663,660, filed Mar. 4, 1978 (now abandoned) which is a CIP of Ser. No. 602,691, filed Aug. 7, 1975 (now abandoned) which is a CIP of Ser. No. 504,924, filed Sept. 11, 1974 (now abandoned).
US Referenced Citations (7)
Non-Patent Literature Citations (1)
Entry |
Fryer, et al., J. Heterocyclic Chemistry, vol. 15, pp. 619-624 (6/78). |
Divisions (1)
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Number |
Date |
Country |
Parent |
905820 |
May 1978 |
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Continuations (1)
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Number |
Date |
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Parent |
663660 |
Mar 1978 |
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Continuation in Parts (2)
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Number |
Date |
Country |
Parent |
602691 |
Aug 1975 |
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Parent |
504924 |
Sep 1974 |
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