Reactions of 4-chloro-1-nitrobenzene with (3-chloro-4-methoxyphenyl)acetonitrile and (3,4-dimethoxyphenyl)acetonitrile; Synthesis of 8-chloro-1-methyl (and methylthiomethyl-6-(3,4-disubstituted phenyl)-4H-s-triazolo[4,3-a]-1,4-benzodiazepines

Abstract

Reactions of 4-chloro-1-nitrobenzene with (3-chloro-4-methoxyphenyl)acetonitrile and (3,4-dimethoxyphenyl)acetonitrile in methanolic potassium hydroxide gave the corresponding 3-aryl-5-chloro-2,1-benzisoxazoles Ia and Ib in good yields; compounds Va, Vb, VI-VIII and X were isolated as by-products and identified by means of spectra. Compounds Ia and Ib were transformed in five steps to the title compounds XVab and XVIab which were found inactive in tests for central depressant and anticonvulsant activity.