Synthesis and Characterization of Azido-Functionalized 1,2,3-Triazole and Fused 1,2,3-Triazole
Yupeng Cao, Haifeng Huang, Limin Wang, Xiangyang Lin, Jun Yang
Abstract
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-2 H -1,2,3-triazole ( 5 ). Starting from 4-amino-1 H -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)-2 H -1,2,3-triazole ( 6 ) (IS = 1 J, v D = 8802 m s –1 ). Additionally, diammonium ( 8 ) and dihydrazinium ( 9 ) salts based on 4-azido-5-(dinitromethyl)-2 H -1,2,3-triazole were also successfully synthesized and characterized. A novel fused nitrogen-rich heterocycle, namely, 6 H -[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 ( T dec = 203 °C) and insensitivity to mechanical stimuli, while the detonation velocity ( v D ) and detonation pressure ( P ) reach 8421 m s –1 and 26.0 GPa, respectively.