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

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

Journal

Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285

Output data

Year: 2021, Volume: 70, Number: 8, Pages: 1599-1604 Pages count : 6 DOI: 10.1007/s11172-021-3256-6

Authors

Gulyaev D.A. ¹ , Klenov M.S. ¹ , Churakov A.M. ¹ , Strelenko Yu.A. ¹ , Pivkina A.N. ² , Tartakovsky V.A. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation
2	N. N. Semenov Federal Research Center for Chemical Physics of the Russian Academy of Sciences, 4 ul. Kosygina, 119991, Moscow, Russian Federation

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).

Gulyaev D.A. , Klenov M.S. , Churakov A.M. , Strelenko Y.A. , Pivkina A.N. , Tartakovsky V.A.
Synthesis of energetic compounds containing (3-nitro-1H-1,2,4-triazol-1-yl)-NNO-azoxy moiety
Russian Chemical Bulletin. 2021. V.70. N8. P.1599-1604. DOI: 10.1007/s11172-021-3256-6 WOS OpenAlex

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