Promising Energetic Asymmetric Bistetrazoles Synthesized via Sequential Cycloaddition Reactions

作者：Jing Liu, Yaqun Dong, Miao Li, Yuji Liu, Wei Huang, Chuan Xiao, Guangbin Cheng, Yongxing Tang · 发表于：The Journal of Organic Chemistry · 年份：2025 · DOI：10.1021/acs.joc.5c00048 · 被引用次数：11 · 研究领域：Energetic Materials and Combustion、Synthesis of Tetrazole Derivatives、Chemical Reaction Mechanisms

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-1 H -pyrazol-3-yl)-2 H -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-1 H -pyrazol-4-yl)-2 H,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.