Reactions of 1,4-dinitroimidazoles with hydrazines

Article abstract of DOI:10.1016/0040-4020(96)00903-9

Reaction of 2-methyl-1,4-dinitroimidazole with hydrazine results in expansion of the imidazole ring and formation of the 1.2.4-triazine derivative. Reaction of 1,4-dinitroimidazole with N-aminomorpholine yields 1-(N-morpholino)-4-nitroimidazole, by degenerative transformation of the imidazole ring. Treatment of 1,4-dinitroimidazoles with t-butoxycarbonylhydrazine results in the break down of the imidazole ring and formation of glyoxal dihydrazone derivatives. Structures of representative heterocyclic products were determined by X-ray analysis.