Diazotization of o -Aminoamidoximes for the Preparation of Energetic 6,5,6-Fused 1,2,3-Triazine-3-oxides.

Two 6,5,6-fused 1,2,3-triazine-3-oxides ( 4 and 6 ) were designed and synthesized via the reaction of o -aminoamidoximes with sodium nitrite. In addition, the ring-opening products ( 5 , 7 , and 8 ) derived from 1,2,3-triazine-3-oxides were isolated and characterized. A comprehensive exploration of the reaction mechanism governing the ring-opening process was performed through a combination of theoretical and experimental studies. Notably, compound 4 exhibited commendable detonation properties and low sensitivity, demonstrating its promising potential as an energetic material.