Synthesis and Characterization of Azido-Functionalized 1,2,3-Triazole and Fused 1,2,3-Triazole

Here, we report the nitration of NH on the 1,2,3-triazole ring and the synthesis of several nitrogen-rich energetic compounds based on key intermediate 4-azido-5-(chlorodinitromethyl)-2-nitro-2H-1,2,3-triazole (5). Starting from 4-amino-1H-1,2,3-triazole-5-carbonitrile (1), we successfully constructed compound 5 through four steps. Subsequently, the dechlorination of compound 5 gave potassium 4-azido-5-(dinitromethyl)-2H-1,2,3-triazole (6) (IS = 1 J, vD = 8802 m s-1). Additionally, diammonium (8) and dihydrazinium (9) salts based on 4-azido-5-(dinitromethyl)-2H-1,2,3-triazole were also successfully synthesized and characterized. A novel fused nitrogen-rich heterocycle, namely, 6H-[1,2,3]triazolo[4,5-d][1,2,3] triazine-6,7-diamine (10), was surprisingly obtained, which has a high nitrogen content of 73.66% and shows good thermal stability (Tdec = 203 degrees C) and insensitivity to mechanical stimuli, while the detonation velocity (vD) and detonation pressure (P) reach 8421 m s-1 and 26.0 GPa, respectively.

Automated summary

In this study, the nitration of NH on the 1,2,3-triazole ring was reported, and several nitrogen-rich energetic compounds were synthesized based on the key intermediate 4-azido-5-(chlorodinitromethyl)-2-nitro-2H-1,2,3-triazole (5). Compound 5 was successfully constructed from 4-amino-1H-1,2,3-triazole-5-carbonitrile (1) through four steps. Furthermore, potassium 4-azido-5-(dinitromethyl)-2H-1,2,3-triazole (6), diammonium (8), and dihydrazinium (9) salts were synthesized and characterized. A novel fused nitrogen-rich heterocycle, 6H-[1,2,3]triazolo[4,5-d][1,2,3] triazine-6,7-diamine (10), with high nitrogen content and good thermal stability, as well as insensitivity to mechanical stimuli, was obtained.