Integration of 1,2,3-Triazine N-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 N-oxide and 2,4,6-trinitroaniline moieties. Starting from the known compound 4,6-diamino-2-chloropyrimidine-5-carbonitrile (1), the nucleophilic substitution followed by one-step nitration introduced three nitro groups onto the benzene ring and 1,2,3-triazine N-oxide moiety, simultaneously. The resulting compounds 4-7 exhibited a high decomposition temperature (Td > 250 °C) as well as relatively good detonation properties and low sensitivities.