The interaction of fluorinated 2-arylhydrazono-1,3-dicarbonyl compounds with o-phenylenediamine

2-Arylhydrazono-3-fluoroaklyl-3-oxo esters react with o-phenylenediamine under neutral conditions to form mainly o-aminoanilides, from which can be obtained 1,5-benzodiazepin-2-ones. Ethyl-2-(benzimidazol-2-yl)-2-(4-methylphenyl)hydrazonoethanoate was isolated also from the reaction of di(tri)fluoromethyl-containing 2-arylhydrazono-3-oxo esters. The reactions of o-phenylenediamine with 1,2,3-triketone 2-arylhydrazones containing alkyl substituents result in the formation of 1-(benzimidazol-2-yl)-1,2-dioxoalkane arylhydrazones, whereas phenylsubstituted analogues afford 2-phenylbenzimidazole. Nickel(II) chelates of N,N′-phenylene-bis(2-arylazo-1,3-aminovinylketones) were obtained from 1,2,3-triketone 2-arylhydrazones and o-phenylenediamine using a template method.