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Communication | Regular issue | Vol 12, No. 4, 1979, pp.489-492
Published online, 1st January, 1970
DOI: 10.3987/R-1979-04-0489
A Facile Synthesis of 4-Phenylcarbostyrils and 4-Phenylisocarbostyril Involving Photocyclization of Benzo[b]thiophene-2-carboxanilidines and 2-Benzoylamino-3-chlorobenzo[b]thiophene

Shinzo Kano,* Toshihiko Ozaki, and Satoshi Hibino

*School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan

Abstract

Photocyclization of 3-chlorobenzo[b]thiophene-2-carboxanilide afforded 1-benzothiophene[2,3-c]quinolin-6-one, which upon desulfurization gave 4-phenylcarbostyril (3a). In this way, 4-phenyl-6-substituted-carbostyrils (3b), (3c), (3d) and (3f) and 8-substituted analogues (6a), (6b) and (6c) were also obtained. This approach to 4-phenylcarbostyrils was applied to a synthesis of 4-phenylisocarbostyril (12) through photocyclization of 2-benzoylamino-3-chlorobenzo[b]thiophene.