Abstract
The reaction of 4-amino-1H-1, 5-benzodiazepine-3-carbonitrile hydrochloride (1) with hydroxylamine gave a ring-opened compound, 3-amino-3-(o-aminoanilino)-2-cyano-2-propenaloxime (5). Compound 5 was converted to 5-(o-aminoanilino)-4-cyanoisoxazole (6) on treatment with hydrochloric acid. Compound 1 was also reacted with methoxyamine to give 2-(1'-cyano-2'-methoxyaminovinyl) benzimidazole (8). On the other hand, hydrolysis of 1 at pH 1 gave 2-cyanomethylbenzimidazole hydrochloride (12).
