Achieving heat-resistant energetic compounds silver-catalyzed one-pot cycloaddition of ethyl 2-isocyanoacetate and nitrogen-rich diazonium

1,2,4-Triazoles are privileged structural motifs found in many fields, including pharmaceuticals and natural products as well as energetic materials. However, the limited synthetic strategies toward 1,2,4-triazoles have hindered the development of new scaffolds. Herein, we first developed an efficient strategy to construct carboxylate triazoles via a silver oxide catalyzed [3 + 2] cycloaddition reaction of heterocyclic diazonium ( 2 , 3 , 4 or 5 ) with ethyl 2-isocyanoacetate. Compounds 2a-5a were fully characterized and were used to prepare four nitrogen-rich heat-resistant explosives TTTN ( 2c ), BTTN ( 3c ), DTTN ( 4c ) and ATTN ( 5c ). All of the compounds ( 2c-5c ) have high nitrogen contents of >50%. In addition, compound ATTN ( 5c ) shows good performances ( D = 8473 m s −1 , P = 25.0 GPa, IS > 40 J, and FS > 360 N) and high thermal stability ( T d = 318 °C), which suggests its potential as a heat-resistant explosive. An efficient strategy of constructing nitrogen-rich 1,2,4-triazole bridged compounds via silver-catalyzed one-pot cycloaddition has been developed, which resulted in the formation of promising heat-resistant materials.