Energetic and Fluorescent Azole-Fused 4‑Amino-1,2,3-triazine-3-N-oxides

Nitrogen-rich heterocyclic fused molecules are of considerable significance in the fields of synthetic and materials chemistry. Here, an efficient strategy for the synthesis of azole fused 4-amino-1,2,3-triazine N-oxides (4-6) via the diazotization reactions of o-amino–aminohydroximoyl nitrogen-rich heterocyclic rings is reported. In addition, several energetic salts (7–12) based on these fused compounds were prepared. These compounds not only show promising properties as energetic materials but also exhibit green fluorescence due to the presence of the triazine N-oxide moiety. The mechanism of the ring-expansion reaction has been explored by the isolation and confirmation of compound 14. They have good detonation performance, especially the hydrazinium salt of 9 with a high density of 1.800 g cm–3, a detonation velocity of 9385 m s–1, as well as a detonation pressure of 33.6 GPa.