Skip to main content
Log in

Synthesis of 3,5-difuroxanyl-1,6-dihydro-1,2,4-triazines

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

Abstract

An approach for the synthesis of the first representatives of 3,5-difuroxanyl-1,6-di-hydro-1,2,4-triazines based on the reaction of (furoxanyl)amidrazones with 4-amino-3-bromoacetylfuroxan under mild conditions was proposed. It was shown that the reaction proceeds via initial alkylation of the starting amidrazones with bromoacetylfuroxan followed by the intramolecular condensation with the formation of dihydro-1,2,4-triazine ring. Attempts to oxidize synthesized heterocyclic systems to fully aromatic derivatives under various conditions were performed.

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

Access this article

Subscribe and save

Springer+ Basic
$34.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or eBook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. P. Das, M. D. Delost, M. H. Qureshi, D. T. Smith, J. T. Njardarson, J. Med. Chem., 2019, 62, 4265.

    Article  CAS  Google Scholar 

  2. S. W. Krska, D. A. DiRocco, S. D. Dreher, M. Shevlin, Acc. Chem. Res., 2017, 50, 2976.

    Article  CAS  Google Scholar 

  3. M. C. Hilton, X. Zhang, B. T. Boyle, J. V. Alegre-Requena, R. S. Paton, A. McNally, Science, 2018, 362, 799.

    Article  CAS  Google Scholar 

  4. L. I. Belen’kii, G. A. Gazieva, Yu. B. Evdokimenkova, N. O. Soboleva, Adv. Heterocycl. Chem., 2020, 132, 385.

    Article  Google Scholar 

  5. N. N. Makhova, L. I. Belen’kii, G. A. Gazieva, I. L. Dalinger, L. S. Konstantinova, V. V. Kuznetsov, A. N. Kravchenko, M. M. Krayushkin, O. A. Rakitin, A. M. Starosotnikov, L. L. Fershtat, S. A. Shevelev, V. Z. Shirinian, V. N. Yarovenko, Russ. Chem. Rev., 2020, 89, 55.

    Article  CAS  Google Scholar 

  6. L. L. Fershtat, E. S. Zhilin, Molecules, 2021, 26, 5705.

    Article  CAS  Google Scholar 

  7. L. L. Fershtat, N. N. Makhova, ChemMedChem, 2017, 12, 622.

    Article  CAS  Google Scholar 

  8. N. N. Makhova, O. A. Rakitin, Chem. Heterocycl. Compd., 2017, 53, 849.

    Article  CAS  Google Scholar 

  9. R. A. M. Serafim, F. G. Pernichelle, E. I. Ferreira, Expert Opin. Drug. Discov., 2017, 12, 941.

    Article  CAS  Google Scholar 

  10. V. G. Granik, N. B. Grigoriev, Russ. Chem. Rev., 2011, 80, 171.

    Article  CAS  Google Scholar 

  11. A. M. Starosotnikov, M. A. Bastrakov, V. A. Kokorekin, Russ. Chem. Bull., 2022, 71, 474.

    Article  CAS  Google Scholar 

  12. L. L. Fershtat, N. N. Makhova, ChemPlusChem, 2020, 85, 13.

    Article  CAS  Google Scholar 

  13. S. G. Zlotin, A. M. Churakov, M. P. Egorov, L. L. Fershtat, M. S. Klenov, I. V. Kuchurov, N. N. Makhova, G. A. Smirnov, Yu. V. Tomilov, V. A. Tartakovsky, Mendeleev Commun., 2021, 31, 731.

    Article  CAS  Google Scholar 

  14. A. A. Larin, A. V. Shaferov, K. A. Monogarov, D. B. Meerov, A. N. Pivkina, L. L. Fershtat, Mendeleev Commun., 2022, 32, 111.

    Article  CAS  Google Scholar 

  15. A. A. Larin, A. V. Shaferov, A. S. Kulikov, A. N. Pivkina, K. A. Monogarov, A. O. Dmitrienko, I. V. Ananyev, D. V. Khakimov, L. L. Fershtat, N. N. Makhova, Chem. Eur. J., 2021, 27, 14628.

    Article  CAS  Google Scholar 

  16. A. A. Larin, D. M. Bystrov, L. L. Fershtat, A. A. Konnov, N. N. Makhova, K. A. Monogarov, D. B. Meerov, I. N. Melnikov, A. N. Pivkina, V. G. Kiselev, N. V. Muravyev, Molecules, 2020, 25, 5836.

    Article  CAS  Google Scholar 

  17. A. A. Larin, A. V. Shaferov, M. A. Epishina, I. N. Melnikov, N. V. Muravyev, I. V. Ananyev, L. L. Fershtat, N. N. Makhova, ACS Appl. Energy Mater., 2020, 3, 7764.

    Article  CAS  Google Scholar 

  18. A. A. Larin, N. V. Muravyev, A. N. Pivkina, K. Yu. Suponitsky, I. V. Ananyev, D. V. Khakimov, L. L. Fershtat, N. N. Makhova, Chem. Eur. J., 2019, 25, 4225.

    Article  CAS  Google Scholar 

  19. O. V. Shabunina, Ya. K. Shtaitz, D. S. Kopchuk, A. P. Krinochkin, S. Santra, G. V. Zyryanov, Z. Wang, V. L. Rusinov, O. N. Chupakhin, Chem. Heterocycl. Compd., 2021, 57, 462.

    Article  CAS  Google Scholar 

  20. V. A. Ivolgina, L. D. Popov, G. A. Gazieva, A. N. Kravchenko, Russ. Chem. Bull., 2020, 69, 2215.

    Article  CAS  Google Scholar 

  21. S. E. Creegan, M. Zeller, E. F. C. Byrd, D. G. Piercey, Cryst. Growth Des., 2021, 21, 3922.

    Article  CAS  Google Scholar 

  22. L. L. Fershtat, A. A. Larin, M. A. Epishina, I. V. Ovchinnikov, A. S. Kulikov, I. V. Ananyev, N. N. Makhova, RSC Adv., 2016, 6, 31526.

    Article  CAS  Google Scholar 

  23. Z. Chen, N. Ren, X. Ma, J. Nie, F.-G. Zhang, J.-A. Ma, ACS Catal., 2019, 9, 4600.

    Article  CAS  Google Scholar 

  24. M. V. Berezin, G. L. Rusinov, V. N. Charushin, Russ. Chem. Bull., 2014, 63, 1359.

    Article  CAS  Google Scholar 

  25. L. L. Fershtat, M. A. Epishina, I. V. Ovchinnikov, V. V. Kachala, N. N. Makhova, Chem. Heterocycl. Compd., 2015, 51, 754.

    Article  CAS  Google Scholar 

  26. A. S. Kulikov, N. N. Makhova, Russ. Chem. Bull., 1998, 47, 139.

    Article  CAS  Google Scholar 

Download references

Funding

This work was financially supported by the Russian Science Foundation (Project No. 21-73-10109).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to L. L. Fershtat.

Additional information

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. 6, pp. 1257–1261, June, 2022.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Degtyarev, D.D., Polkovnichenko, M.S., Larin, A.A. et al. Synthesis of 3,5-difuroxanyl-1,6-dihydro-1,2,4-triazines. Russ Chem Bull 71, 1257–1261 (2022). https://doi.org/10.1007/s11172-022-3527-x

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-022-3527-x

Key words

Navigation