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.