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

ABSTRACT

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.