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Oxidative Cyclization Protocol for the Preparation of Energetic 3-Amino-5- R-1,2,4-oxadiazoles.

An efficient method has been developed for the synthesis of energetic 3-amino-5- R-1,2,4-oxadiazoles via iodobenzene diacetate (IBD)-mediated oxidative cyclization in high yields at ambient temperature. Compound 1c has a graphite-like structure, which has seldom been reported in bicyclic compounds. The reaction of 3-amino-5- R-1,2,4-oxadiazole derivatives with hydrazine monohydrate in THF gives products that are a function of the substituent. Energetic performance calculations show detonation properties superior to TNT with concomitant lower impact and friction sensitivities.