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Synthesis of 3-dinitromethyl-1,2,4-oxadiazoles from dinitroacetamidoximes

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Abstract

It was demonstrated that the amidoxime moiety of potassium salt of dinitroacetamidoxime is capable of cyclocondensation to form the 1,2,4-oxadiazole ring.

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References

  1. T. D. Ladyzhnikova, K. V. Altukhov, N. A. Solov’ev, Zh. Organicheskoi Khimii [J. Org. Chem. USSR], 1986, 22, 2618 (in Russian).

    CAS  Google Scholar 

  2. A. G. Tyrkov, Russ. J. Org. Chem., 2002, 38, 1218; DOI: https://doi.org/10.1023/A:1020934400960.

    Article  CAS  Google Scholar 

  3. A. G. Tyrkov, V. V. Resnyanskii, Izyestiya vysshikh uchebnykh zavedenii, Seriya khimiya i khimicheskaya tekhnologiya [Bulletin of Universities, Series of Chemistry and Chemical Technology], 1994, 37, Nos 10–12, 131 (in Russian).

    CAS  Google Scholar 

  4. A. G. Tyrkov, B. G. Suikhanova, Russ. J. Org. Chem., 1999, 35, 1299.

    CAS  Google Scholar 

  5. I. A. Shevtsova, A. G. Tyrkov, Russ. J. Org. Chem., 2007, 43, 1742; DOI: https://doi.org/10.1134/S1070428007110309.

    Article  CAS  Google Scholar 

  6. M. A. Abdelrakhim, A. G. Tyrkov, E. A. Yurtaeva, Russ. J. Org. Chem., 2014, 50, 280; DOI: https://doi.org/10.1134/S1070428014020237.

    Article  CAS  Google Scholar 

  7. A. G. Tyrkov, K. P. Paschenkko, T. D. Ladyzhnikova, K. V. Altukhov, Izvestiya vysshikh uchebnykh zavedenii, Seriya khimiya i khimicheskaya tekhnologiya [Bulletin of Universities, Series of Chemistry and Chemical Technology], 2004, 47, No. 7, 148 (in Russian).

    CAS  Google Scholar 

  8. C. Yan, K. Wang, T. Liu, H. Yang, G. Cheng, Q. Zhang, Dalton Trans., 2017, 46, 14210; DOI: https://doi.org/10.1039/C7DT03320F.

    Article  CAS  Google Scholar 

  9. T. S. Hermann, T. M. Klapotke, B. Krumm, J. Stierstorfer, Asian J. Org. Chem., 2018, 7, 739; DOI: https://doi.org/10.1002/ajoc.201700698.

    Article  CAS  Google Scholar 

  10. C. He, G. H. Imler, D. A. Parrish, J. M. Shreeve, J. Mater. Chem. A, 2018, 6, 16833; DOI: https://doi.org/10.1039/C8TA06199H.

    Article  CAS  Google Scholar 

  11. T. Lu, C. Wang, G. Wang, S. Wang, J. Song, H. Yin, G. Fan, F.-X. Chen, New J. Chem., 2019, 43, 13330; DOI: https://doi.org/10.1039/C9NJ01452G.

    Article  CAS  Google Scholar 

  12. T. Lu, Y. He, J. Song, Z. Hou, H. Yin, G. Fan, F.-X. Chen, New J. Chem., 2021, 45, 526; DOI: https://doi.org/10.1039/D0NJ05530A.

    Article  CAS  Google Scholar 

  13. J. Zhou, J. Zhang, B. Wang, L. Qiu, A. B. Sheremetev, FirePhysChem, 2022, 2, 83; DOI: https://doi.org/10.1016/j.fpc.2021.09.005.

    Article  Google Scholar 

  14. W.-L. Cao, Q. N. Tariq, Z.-M. Li, J.-Q. Yang, J.-G. Zhang, Defence Technology, 2022, 18, 344; DOI: https://doi.org/10.1016/j.dt.2021.12.002.

    Article  Google Scholar 

  15. L. A. Kayukova, Pharm. Chem. J., 2005, 39, 539; DOI: https://doi.org/10.1007/s11094-006-0017-7.

    Article  CAS  Google Scholar 

  16. A. G. Tyrkov, 1,2,4-Oksadiazoly: Sintez, stroyenie, svoystva i primenenie [1,2,4-Oxadiazoles: Synthesis, Structure, Properties, and Applications], Publishing house of the Astrakhan State University, 2003 (in Russian).

  17. A. Pace, P. Pierro, Org. Biomol. Chem., 2009, 7, 4337; DOI: https://doi.org/10.1039/B908937C.

    Article  CAS  Google Scholar 

  18. A. Pace, S. Buscemi, A. P. Piccionello, I. Pibiri, Adv. Heterocycl. Chem., 2015, 116, 85; DOI: https://doi.org/10.1016/bs.ai-hch.2015.05.001.

    Article  CAS  Google Scholar 

  19. T. E. Khoranyan, T. K. Shkineva, I. A. Vatsadze, A. Kh. Shakhnes, N. V. Muravyev, A. B. Sheremetev, I. L. Dalinger, Chem. Heterocycl. Compd., 2022, 58, 37; DOI: https://doi.org/10.1007/s10593-022-03054-1.

    Article  CAS  Google Scholar 

  20. T. E. Khoranyan, O. V. Serushkina, I. A. Vatsadze, K. Yu. Suponitskiy, K. A. Monogarov, T. K. Shkineva, I. L. Dalinger, Russ. Chem. Bull., 2022, 71, 1750.

    Article  CAS  Google Scholar 

  21. A. E. Frumkin, N. V. Yudin, K. Yu. Suponitsky, A. B. Sheremetev, Mendeleev Commun., 2018, 28, 135; DOI: https://doi.org/10.1016/j.mencom.2018.03.007.

    Article  CAS  Google Scholar 

  22. A. E. Frumkin, A. A. Anisimov, A. B. Sheremetev, Russ. Chem. Bull., 2018, 67, 2058; DOI: https://doi.org/10.1007/s11172-018-2329-7.

    Article  CAS  Google Scholar 

  23. APEX2 and SAINT, Bruker AXS Inc., Madison, Wisconsin, USA, 2014.

  24. G. M. Sheldrick, Acta Crystallogr. Sect. C Structural Chemistry, 2015, 71, 3; DOI: https://doi.org/10.1107/S2053229614024218.

    Article  Google Scholar 

  25. M. J. Kamlet, R. E. Oesterling, H. G. Adolph, J. Chem. Soc., 1965, 5838; DOI: https://doi.org/10.1039/JR9650005838.

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Authors and Affiliations

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

    A. E. Frumkin, K. Yu. Suponitsky & A. B. Sheremetev

Authors
  1. A. E. Frumkin
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  2. K. Yu. Suponitsky
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  3. A. B. Sheremetev
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Corresponding author

Correspondence to A. B. Sheremetev.

Additional information

Dedicated to Academician of the Russian Academy of Sciences V. A. Tartakovskiy on the occasion of his 90th birthday.

No human or animal subjects were used in this research.

The authors declare no competing interests.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 2012–2015, September, 2022.

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Frumkin, A.E., Suponitsky, K.Y. & Sheremetev, A.B. Synthesis of 3-dinitromethyl-1,2,4-oxadiazoles from dinitroacetamidoximes. Russ Chem Bull 71, 2012–2015 (2022). https://doi.org/10.1007/s11172-022-3622-z

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  • DOI: https://doi.org/10.1007/s11172-022-3622-z

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