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

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 7, 2025

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

Language: Английский

Design and Synthesis of Bistetrazole-Based Energetic Salts Bearing the Nitrogen-Rich Fused Ring

Organic Letters, Journal Year: 2023, Volume and Issue: 25(30), P. 5661 - 5665

Published: July 20, 2023

A series of bistetrazole-based energetic salts bearing a nitrogen-rich fused ring were designed and synthesized. Among them, compounds 4-10 showed good detonation properties excellent thermostability. By treating 3 with concentrated hydrochloric acid, new type Dimroth rearrangement was observed that afforded compound 12 efficiently. This transformation herein constitutes valuable addition to the rearrangement.

Language: Английский

Assembling tetrazole-rings on a fused ring framework: toward energetic materials with enhanced performance

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(15), P. 3799 - 3804

Published: Jan. 1, 2023

A series of nitrogen-rich fused ring energetic compounds assembled with different numbers tetrazole rings were achieved by the classic Dimroth rearrangement (DR) reaction.

Language: Английский