Synthesis of energetic compounds containing (3-nitro-1H-1,2,4-triazol-1-yl)-NNO-azoxy moiety

• DOI: 10.1007/s11172-021-3256-6
• Publication Date: 2021-09-01T16:03:28Z
• Authors: D. A. Gulyaev; M. S. Klenov; A. M. Churakov; Yu. A. Strelenko; A. N. Pivkina; V. A. Tartakovsky
• Keywords: Azoxy; Moiety

The reaction of 3-amino-4-[(3-nitro-1H-1,2,4-triazol-1-yl)-NNO-azoxy]furazan (4a) with 2,2,2-trifluoro-N-(4-nitrosofurazan-3-yl)acetamide (6) in the presence of dibromoisocyanuric acid (DBI) followed by removal of the protective trifluoroacetyl group gives 3-amino-4-({4-[(3-nitro-1H-1,2,4-triazol-1-yl)-NNO-azoxy]furazan-3-yl}-NNO-azoxy)furazan (5a). This compound contains a new explosophore (3-nitro-1H-1,2,4-triazol-1-yl)-NNO-azoxy moiety. The oxidation of the amino group in aminofurazan 5a with an excess N2O5 of resulted in the corresponding nitro derivative 5b. Aminofurazan 5a reacted with DBI to give the corresponding azo compound 5c. Compounds 5a,c may be of interest as energetic substances due to the combination of good thermal stability and high calculated enthalpy of formation (827 and 953 kcal kg−1, respectively).