Skip to main content
SpringerLink
Log in

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

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

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).

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. O. T. O’Sullivan, M. J. Zdilla, Chem. Rev., 2020, 120, 5682.

    Article  Google Scholar 

  2. L. L. Fershtat, N. N. Makhova, Russ. Chem. Rev., 2016, 85, 1097.

    Article  CAS  Google Scholar 

  3. S. G. Zlotin, I. L. Dalinger, N. N. Makhova, V. A. Tartakovsky, Russ. Chem. Rev., 2020, 89, 1.

    Article  CAS  Google Scholar 

  4. H. Gao, Q. Zhang, J. M. Shreeve, J. Mater. Chem. A, 2020, 8, 4193.

    Article  CAS  Google Scholar 

  5. D. E. Chavez, Top. Heterocycl. Chem., 2017, 1.

  6. A. B. Sheremetev, V. O. Kulagina, N. S. Aleksandrova, D. E. Dmitriev, Y. A. Strelenko, V. P. Lebedev, Y. N. Matyushin, Propellants, Explos., Pyrotech., 1998, 23, 142.

    Article  CAS  Google Scholar 

  7. N. E. Leonov, M. S. Klenov, O. V. Anikin, A. M. Churakov, Y. A. Strelenko, A. A. Voronin, D. B. Lempert, N. V. Muravyev, I. V. Fedyanin, S. E. Semenov, V. A. Tartakovsky, ChemistrySelect, 2020, 5, 12243.

    Article  CAS  Google Scholar 

  8. O. V. Anikin, N. E. Leonov, M. S. Klenov, A. M. Churakov, A. A. Voronin, A. A. Guskov, N. V. Muravyev, Yu. A. Strelenko, I. V. Fedyanin, V. A. Tartakovsky, Eur. J. Org. Chem., 2019, 26, 4189.

    Article  Google Scholar 

  9. M. S. Klenov, N. E. Leonov, A. A. Guskov, A. M. Churakov, Yu. A. Strelenko, V. A. Tartakovsky, Russ. Chem. Bull., 2019, 68, 1798.

    Article  CAS  Google Scholar 

  10. O. A. Luk’yanov, G. V. Pokhvisneva, T. V. Ternikova, N. I. Shlykova, M. E. Shagaeva, Russ. Chem. Bull., 2011, 60, 1703.

    Article  Google Scholar 

  11. O. A. Luk’yanov, V. V. Parakhin, Russ. Chem. Bull., 2012, 61, 1582.

    Article  Google Scholar 

  12. G. A. Smirnov, O. A. Luk’yanov, Russ. Chem. Bull., 2020, 69, 295.

    Article  CAS  Google Scholar 

  13. V. P. Grachev, I. N. Zyuzin, S. V. Kurmaz, E. V. Vaganov, R. I. Komendant, D. B. Lempert, Russ. Chem. Bull., 2020, 69, 2312.

    Article  CAS  Google Scholar 

  14. M. S. Klenov, A. A. Guskov, O. V. Anikin, A. M. Churakov, Y. A. Strelenko, I. V. Fedyanin, K. A. Lyssenko, V. A. Tartakovsky, Angew. Chem., Int. Ed., 2016, 55, 11472.

    Article  CAS  Google Scholar 

  15. A. A. Konnov, M. S. Klenov, A. M. Churakov, Yu. A. Strelenko, A. O. Dmitrienko, L. N. Puntus, K. A. Lyssenko, V. A. Tartakovsky, Asian J. Org. Chem., 2018, 7, 2534.

    Article  CAS  Google Scholar 

  16. A. A. Guskov, M. S. Klenov, A. M. Churakov, V. A. Tartakovsky, Russ. Chem. Bull., 2016, 65, 2763.

    Article  CAS  Google Scholar 

  17. H. Wei, H. Gao, J. M. Shreeve, Chem. Eur. J., 2014, 20, 16943.

    Article  CAS  Google Scholar 

  18. D. E. Chavez, D. A. Parrish, L. Mitchell, G. H. Imler, Angew. Chem., Int. Ed., 2017, 56, 3575.

    Article  CAS  Google Scholar 

  19. A. Gunasekaran, M. L. Trudell, J. H. Boyer, Heteroat. Chem., 1994, 5, 441.

    Article  CAS  Google Scholar 

  20. N. Fischer, K. Hüll, T. M. Klapötke, J. Stierstorfer, G. Laus, M. Hummel, C. Froschauer, K. Wurstb, H. Schottenbergerb, Dalton Trans., 2012, 41, 11201.

    Article  CAS  Google Scholar 

  21. T. S. Novikova, T. M. Mel’nikova, O. V. Kharitonova, V. O. Kulagina, N. S. Aleksandrova, A. B. Sheremetev, T. S. Pivina, L. I. Khmel’nitskii, S. S. Novikov, Mendeleev Commun., 1994, 4, 138.

    Article  Google Scholar 

  22. R. M. Moriarty, T. E. Hopkins, I. Prakash, B. K. Vaid, R. K. Vaid, Synth. Commun., 1990, 20, 2353.

    Article  CAS  Google Scholar 

  23. S. E. Semenov, A. M. Churakov, L. F. Chertanova, Yu. A. Strelenko, S. L. Ioffe, V. A. Tartakovskii, Russ. Chem. Bull., 1992, 41, 277.

    Article  Google Scholar 

  24. D. A. Gulyaev, M. S. Klenov, A. M. Churakov, Y. A. Strelenko, I. V. Fedyanin, D. B. Lempert, E. K. Kosareva, T. S. Kon’kova, Y. N. Matyushin, V. A. Tartakovsky, RSC Adv., 2021, 11, 24013.

    Article  CAS  Google Scholar 

  25. L. V. Batog, V. Yu. Rozhkov, E. V. Shatunova, M. I. Struchkova, Russ. Chem. Bull., 2008, 57, 165.

    Article  CAS  Google Scholar 

  26. A. M. Churakov, S. E. Semenov, S. L. Ioffe, Y. A. Strelenko, V. A. Tartakovskii, Mendeleev Commun., 1995, 5, 102.

    Article  Google Scholar 

  27. P. Yin, J. M. Shreeve, Angew. Chem., Int. Ed., 2015, 54, 14513.

    Article  CAS  Google Scholar 

  28. D. E. Dmitriev, Yu. A. Strelenko, A. B. Sheremetev, Russ. Chem. Bull., 2013, 62, 504.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    D. A. Gulyaev, M. S. Klenov, A. M. Churakov, Yu. A. Strelenko & V. A. Tartakovsky

  2. N. N. Semenov Federal Research Center for Chemical Physics of the Russian Academy of Sciences, 4 ul. Kosygina, 119991, Moscow, Russian Federation

    A. N. Pivkina

Authors
  1. D. A. Gulyaev
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. S. Klenov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. M. Churakov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Yu. A. Strelenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. A. N. Pivkina
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. V. A. Tartakovsky
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to M. S. Klenov.

Additional information

The authors are grateful to I. V. Fedyanin and A. O. Dmitrienko (A. N. Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences) for performing the X-ray powder diffraction analysis.

This work was financially supported by the Russian Science Foundation (Project No. 19-13-00276).

This paper does not contain descriptions of studies on animals or humans.

The authors declare no competing interests.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1599–1604, August, 2021.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Gulyaev, D.A., Klenov, M.S., Churakov, A.M. et al. Synthesis of energetic compounds containing (3-nitro-1H-1,2,4-triazol-1-yl)-NNO-azoxy moiety. Russ Chem Bull 70, 1599–1604 (2021). https://doi.org/10.1007/s11172-021-3256-6

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-021-3256-6

Key words

Search

Navigation