Reactivity of 3,5-bis-(4-amino-1,2,5-oxadiazol-3-yl)-1,2,4-triazole

Abstract

Alkylation of 3,5-bis(4-amino-1,2,5-oxadiazol-3-yl)-1,2,4-triazole with haloalkanes afforded N-CH 2 R derivatives, and nitration furnished the corresponding bis-N-nitramine isolated as a trisodium salt. Treatment of the latter with CH 3 I resulted in denitration. Diazotization and oxidation of 3,5-bis(4-amino-1,2,5-oxadiazol-3-yl)-1,2,4-triazole, its N-methyl and N-carboxy derivatives gave rise to the corresponding azido and nitro derivatives. Salts of 3,5-bis(4-amino-1,2,5-oxadiazol-3-yl)-1,2,4-triazol-5-acetic acid with nitrogen-containing bases were synthesized. It was established that the character of reaction products of 3,5-bis(4-amino-1,2,5-oxadiazol-3-yl)-1,2,4-triazole with formaldehyde depended on the acid-base properties of the medium.

Combination of 1,2,4‐Oxadiazole and 1,2,5‐Oxadiazole Moieties for the Generation of High‐Performance Energetic Materials

“…[4] 1,2,5-Oxadiazole (furazan) is highly energetic and has potential use in both propellant and explosive formulations. [3a-e] A large number of nitro-, amino-, and nitramine-functionalized monofurazan compounds, [5] macrocyclic furazans, [6] linked furazans, [7] and ring-fused furazans bridged by azo,o xy,a nd azoxy groups have been reported. [8] However,1 ,2,4-oxadia-zoles [3f-l] and 1,3,4-oxadiazoles [3n-q] have been studied only rarely as energetic materials.…”

Reactions of 3-amino-4-methylfurazan with nitrating agents

“…10), HNO 3 /H 2 SO 4 (see Refs 5,13), and HNO 3 /AcOH (see Ref. 16) mixtures. Treatment of aminofurazans with excess N 2 O 5 (see Refs 12,17) or NO 2 BF 4 (see Refs 17,18) affords nitro derivatives of furazan; however, this process also goes through nitramine formation.…”

Small Cation‐Based High‐Performance Energetic Nitraminofurazanates

“…3,5‐Bis(4‐amino‐1,2,5‐oxadiazol‐3‐yl)‐1,2,4‐triazole (1.00 g, 4.25 mmol) was added in portions to 100 % HNO 3 (3 mL) at 0 °C. After stirring for additional 1 h, the reaction mixture was poured into ice water (50 mL), and extracted with diethyl ether (20 mL×3).…”