Promising Energetic Asymmetric Bistetrazoles Synthesized via Sequential Cycloaddition Reactions

Herein, we report the successful synthesis of a series of asymmetric bistetrazole-based energetic compounds (4, 8, 4a-c, and 5a-c) starting from 2-(5-amino-4-nitro-1H-pyrazol-3-yl)-2H-5-cyanotetrazol (3), which was obtained via the reaction of 3,5-diamino-4-nitropyrazole hydrochloride with diazoacetonitrile using a [3 + 2] cycloaddition strategy. All newly synthesized compounds displayed superior detonation performances, particularly 2'-(5-amino-4-nitro-1H-pyrazol-4-yl)-2H,2'H-5,5'-bistetrazole (4), which exhibited exceptional overall performances. These findings underscore the potential of asymmetric bistetrazole derivatives as promising candidates for the development of advanced energetic materials.