5-Oxo-1H-4,5-dihydro-1,2,4-benzotriazepines. Chemical behavior towards alkylating,acidic and alkaline agents

The chemical behavior of 4-methyl and 4-phenyl-5-oxo-1H-4,5-dihydro-1,2,4-benzotriazepines towards methylating and acidic agents has been investigated. The 4-methyl derivative, when treated with methyl fluorosulfonate furnished, after crystallization from water, a quaternary salt (2,4-dimethyl-5-oxo-1H-4,5-dihydro-1,2,4-benzotriazepinium fluorosulfonate), whereas from the 4-phenyl derivative, a complex mixture was obtained, which, after boiling with water, afforded 2-methylindazolone, aniline fluorosulfonate and formic acid. In acidic medium the 4-methyl derivative underwent an isomerization reaction yielding 1-imino-3-methylquinazolin-4-one, but the 4-phenyl derivative exclusively yielded products resulting from ring opening. In alkaline medium, both compounds gave hydrolytic cleavage products.