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.