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Synthesis of energetic compounds bearing a (3,4-dinitro-1H-pyrazol-1-yl)-NNO-azoxy group

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Abstract

Energetic compounds containing a new explosophoric fragment, (3,4-dinitro-1H-pyrazol-1-yl)-NNO-azoxy group, and furazan rings linked by azo and azoxy bridges were synthesized. Furazans obtained combine a high calculated enthalpy of formation and acceptable thermal stability and are of interest as potential components of energy-rich materials.

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References

  1. O. T. O’Sullivan, M. J. Zdilla, Chem. Rev., 2020, 120, 5682; DOI: https://doi.org/10.1021/acs.chemrev.9b00804.

    Article  Google Scholar 

  2. D. M. Bystrov, L. L. Fershtat, N. N. Makhova, Chem. Heterocycl. Compd. (Engl. Transl.), 2019, 55, 1143; DOI: https://doi.org/10.1007/s10593-019-02593-4.

    Article  CAS  Google Scholar 

  3. S. G. Zlotin, I. L. Dalinger, N. N. Makhova, V. A. Tartakovsky, Russ. Chem. Rev., 2020, 89, 1; DOI: https://doi.org/10.1070/RCR4908.

    Article  CAS  Google Scholar 

  4. H. Gao, Q. Zhang, J. M. Shreeve, J. Mater. Chem. A, 2020, 8, 4193; DOI: https://doi.org/10.1039/C9TA12704F.

    Article  CAS  Google Scholar 

  5. D. E. Chavez, Top. Heterocycl. Chem., 2017, 1; DOI: https://doi.org/10.1007/7081_2017_5.

  6. N. S. Aleksandrova, K. A. Monogarov, A. B. Sheremetev, Chem. Heterocycl. Compd. (Engl. Transl.), 2020, 56, 619; DOI: https://doi.org/10.1007/s10593-020-02709-1.

    Article  CAS  Google Scholar 

  7. I. L. Dalinger, K. Y. Suponitsky, T. K. Shkineva, D. B. Lempert, A. B. Sheremetev, J. Mater. Chem. A, 2018, 6, 14780; DOI: https://doi.org/10.1039/C8TA05179H.

    Article  CAS  Google Scholar 

  8. 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; DOI: https://doi.org/10.1002/(SICI)1521-4087(199806)23:3<142::AID-PREP142>3.0.CO;2-X.

    Article  CAS  Google Scholar 

  9. 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; DOI: https://doi.org/10.1002/slct.202003182.

    Article  CAS  Google Scholar 

  10. A. Gunasekaran, M. L. Trudell, J. H. Boyer, Heteroat. Chem., 1994, 5, 441; DOI: https://doi.org/10.1002/hc.520050505.

    Article  CAS  Google Scholar 

  11. N. Fischer, K. Hüll, T. M. Klapötke, J. Stierstorfer, G. Laus, M. Hummel, C. Froschauer, K. Wurstb, H. Schottenbergerb, Dalton Trans., 2012, 41, 11201; DOI: https://doi.org/10.1039/C2DT30684K.

    Article  CAS  Google Scholar 

  12. 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; DOI: https://doi.org/10.1002/ange.201605611.

    Article  CAS  Google Scholar 

  13. 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; DOI: https://doi.org/10.1002/ajoc.201800545.

    Article  CAS  Google Scholar 

  14. A. A. Guskov, M. S. Klenov, A. M. Churakov, V. A. Tartakovsky, Russ. Chem. Bull., 2016, 65, 2763; DOI: https://doi.org/10.1007/s11172-016-1650-2.

    Article  CAS  Google Scholar 

  15. H. Wei, H. Gao, J. M. Shreeve, Chem. Eur. J., 2014, 20, 16943; DOI: https://doi.org/10.1002/chem.201405122.

    Article  CAS  Google Scholar 

  16. D. E. Chavez, D. A. Parrish, L. Mitchell, G. H. Imler, Angew. Chem. Int. Ed., 2017, 56, 3575; DOI: https://doi.org/10.1002/anie.201612496.

    Article  CAS  Google Scholar 

  17. 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; DOI: https://doi.org/10.1002/ejoc.201900314.

    Article  Google Scholar 

  18. M. S. Klenov, N. E. Leonov, A. A. Guskov, A. M. Churakov, Yu. A. Strelenko, V. A. Tartakovsky, Russ. Chem. Bull., 2019, 68, 1798; DOI: https://doi.org/10.1007/s11172-019-2628-7.

    Article  CAS  Google Scholar 

  19. O. A. Luk’yanov, G. V. Pokhvisneva, T. V. Ternikova, N. I. Shlykova, M. E. Shagaeva, Russ. Chem. Bull., 2011, 60, 1703; DOI: https://doi.org/10.1007/s11172-011-0254-0.

    Article  Google Scholar 

  20. O. A. Luk’yanov, V. V. Parakhin, Russ. Chem. Bull., 2012, 61, 1582; DOI: https://doi.org/10.1007/s11172-012-0210-7.

    Article  Google Scholar 

  21. G. A. Smirnov, O. A. Luk’yanov, Russ. Chem. Bull., 2020, 69, 295; DOI: https://doi.org/10.1007/s11172-020-2759-x.

    Article  CAS  Google Scholar 

  22. V. P. Grachev, I. N. Zyuzin, S. V. Kurmaz, E. V. Vaganov, R. I. Komendant, D. B. Lempert, Russ. Chem. Bull., 2020, 69, 2312; DOI: https://doi.org/10.1007/s11172-020-3037-7.

    Article  CAS  Google Scholar 

  23. D. A. Gulyaev, M. S. Klenov, A. M. Churakov, Y. A. Strelenko, I. V. Fedyanin, D. B. Lempert, N. V. Muravyev, T. S. Kon’kova, Y. N. Matyushin, V. A. Tartakovsky, RSC Advances, 2021, 11, 24013; DOI: https://doi.org/10.1039/D1RA03919A.

    Article  CAS  Google Scholar 

  24. D. A. Gulyaev, M. S. Klenov, A. M. Churakov, Yu. A. Strelenko, A. N. Pivkina, V. A. Tartakovsky, Russ. Chem. Bull., 2021, 70, 1599; DOI: https://doi.org/10.1007/S11172-021-3256-6.

    Article  CAS  Google Scholar 

  25. L. V. Batog, V. Yu. Rozhkov, E. V. Shatunova, M. I. Struchkova, Russ. Chem. Bull., 2008, 57, 165; DOI: https://doi.org/10.1007/s11172-008-0024-9.

    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; https://doi.org/10.1070/MC1995v005n03ABEH000477.

    Article  Google Scholar 

  27. 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; DOI: https://doi.org/10.1070/MC1994v004n04ABEH000386.

    Article  Google Scholar 

  28. P. Yin, J. Zhang, C. He, D. A. Parrish, J. M. Shreeve, J. Mater. Chem. A, 2014, 2, 3200; DOI: https://doi.org/10.1039/C3TA15057G.

    Article  CAS  Google Scholar 

  29. D. E. Dmitriev, Yu. A. Strelenko, A. B. Sheremetev, Russ. Chem. Bull., 2013, 62, 504; DOI: https://doi.org/10.1007/s11172-013-0070-9.

    Article  CAS  Google Scholar 

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Funding

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

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Correspondence to M. S. Klenov.

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Dedicated to Academician of the Russian Academy of Sciences O. M. Nefedov on the occasion of his 90th birthday.

A. A. Konnov, M. S. Klenov, A. M. Churakov, I. M. Dubrovin, I. L. Dalinger, Yu. A. Strelenko, I. V. Fedyanin, D. B. Lempert, E. K. Kosareva, T. S. Kon’kova, Y. N. Matyushin, V. A. Tartakovsky, Novel energetic compounds containing(3,4-dinitro-1H-pyrazol-1-yl)-NNO-azoxy and (3,5-dinitro-1H-pyrazol-1-yl)-NNO-azoxy moieties: synthesis and characterization, Asian J. Org. Chem., 2021, in press.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2189–2194, November, 2021.

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

The authors declare no competing interests.

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Konnov, A.A., Dubrovin, I.M., Klenov, M.S. et al. Synthesis of energetic compounds bearing a (3,4-dinitro-1H-pyrazol-1-yl)-NNO-azoxy group. Russ Chem Bull 70, 2189–2194 (2021). https://doi.org/10.1007/s11172-021-3331-z

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  • DOI: https://doi.org/10.1007/s11172-021-3331-z

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