Synthetic Routes to a Triazole and Tetrazole with Trinitroalkyl Substitution at Nitrogen

Two N-substituted trinitroalkyl azoles, one triazole, and one tetrazole were synthesized and isolated via efficient cyclization reactions. Both materials were thoroughly characterized, and their structures were confirmed by X-ray diffraction. The formation of the N-trinitroethyl substituted triazole proceeds unexpectedly via nitrosation of an N-substituted diaminomaleonitrile initially with HNO3 and subsequently confirmed with HNO2. The N-trinitropropyl substituted tetrazole was prepared via a standard cyclization route from trinitropropylammonium chloride with orthoformate and azide.