Integration of 1,2,3-Triazine <i>N</i>-Oxide and 2,4,6-Trinitroaniline Moieties for the Design of Heat-Resistant Energetic Compounds

Heat-resistant energetic compounds are of great importance in the field of energetic material chemistry. Here, we report a practical synthesis of a series of fused-ring energetic compounds via the combination of 1,2,3-triazine <i>N</i>-oxide and 2,4,6-trinitroaniline moieties. Starting from the known compound 4,6-diamino-2-chloropyrimidine-5-carbonitrile (<b>1</b>), the nucleophilic substitution followed by one-step nitration introduced three nitro groups onto the benzene ring and 1,2,3-triazine <i>N</i>-oxide moiety, simultaneously. The resulting compounds <b>4</b>-<b>7</b> exhibited a high decomposition temperature (<i>T</i>_d > 250 °C) as well as relatively good detonation properties and low sensitivities.