Azolyl derivatives of nitrohalobutadienes: V. New route to functionally substituted benzazetines

Heating of 1-azolyl-1-(4-R-phenylamino)-2-nitro-3,4,4-trichloro-1,3-butadie nes and 1-azolyl-1-(4-R-phenylamino)-2-nitro-3,4-dichloro-4-bromo-1,3-butad ienes (R = BuO, EtO, MeO, Me; azolyl = 1-benzotriazolyl, 3,5-dimethyl-1-pyr azolyl, and 1,2,4-triazol-1-yl) in methanol or acetic acid gave the corresp onding 2-(1-nitrotrihalopropenylidene)-4-R-benzazetines. The latter reacted with amines, sodium alkoxides, and sodium thiolates, affording salts of th e aci-nitro form. The reactions with benzoyl chloride and chloroacetyl chlo ride in the presence of pyridine led to formation of mixed anhydrides.