Skip to main content
Log in

Recent progress in the synthesis of nitroisoxazoles and their hydrogenated analogs via [3+2] cycloaddition reactions (microreview)

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

In this microreview, the application of [3+2] cycloaddition reactions for the selective preparation of nitroisoxazoles and their hydrogenated analogs was analyzed on the basis of recent publications. It was found that most discussed processes are realized at room temperature with high or full selectivity.

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

Access this article

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. Danyliuk, I. Yu.; Vovk, M. V. Chem. Heterocycl. Compd. 2022, 58, 567.

    Article  CAS  Google Scholar 

  2. Obernikhina, N. V.; Kachaeva, M. V.; Kachkovsky, O. D.; Brovarets, V. S. Chem. Heterocycl. Compd. 2022, 58, 412.

    Article  CAS  Google Scholar 

  3. Mitra, A. K. Chem. Heterocycl. Compd. 2022, 58, 178.

    Article  CAS  Google Scholar 

  4. Zawadzińska, K.; Gostyński, B. Sci. Radices 2023, 2, 25.

    Article  Google Scholar 

  5. Ono, N. The Nitro Group in Organic Synthesis; Wiley: New York, 2001.

    Book  Google Scholar 

  6. Siadati, S. A.; Rezazadeh, S. Sci. Radices 2022, 1, 46.

    Article  Google Scholar 

  7. Rios-Gutierrez, M.; Domingo, L. R. Eur. J. Org. Chem. 2019, 267.

  8. Pakravan, P.; Siadati, S. A. Progress React. Kinet. Mech. 2016, 41, 331.

    Article  Google Scholar 

  9. Vasilenko, D. A.; Sadovnikov, K. S.; Sedenkova, K. N.; Karlov, D. S.; Radchenko, E. V.; Grishin, Y. K.; Rybakov, V. B.; Kuznetsova, T. S.; Zamoyski, V. L.; Grigoriev, V. V.; Palyulin, V. A.; Averina, E. B. Molecules 2021, 26, 6411.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  10. Labriere, C.; Talapatra, S. K.; Thoret, S.; Bougeret, C.; Kozielski, F.; Guillou, C. Bioorg. Med. Chem. 2016, 24, 721.

    Article  CAS  PubMed  Google Scholar 

  11. Kras, J.; Sadowski, M.; Zawadzińska, K.; Nagatsky, R.; Wolinski, P.; Kula, K.; Łapczuk, A. Sci. Radices 2023, 2, 247.

    Article  Google Scholar 

  12. Dresler, E.; Alnajjar, R.; Jasiński, R. Sci. Radices 2023, 2, 69.

    Article  Google Scholar 

  13. Jasiński, R. Monatsh. Chem. 2015, 146, 591.

    Article  PubMed  PubMed Central  Google Scholar 

  14. Huang, H.; Pu, Y.; Zhu, D.; Zhang, C.; Yang, J.; Liu, C.; Zhang, X.; Tao, F.; Li, M.-M.; Lu, J. Tetrahedron 2023, 131, 133203.

    Article  CAS  Google Scholar 

  15. Zawadzińska, K.; Ríos-Gutiérrez, M.; Kula, K.; Woliński, P.; Mirosław, B.; Krawczyk, T.; Jasiński, R. Molecules 2021, 26, 6774.

    Article  PubMed  PubMed Central  Google Scholar 

  16. Kula, K.; Zawadzińska, K. Curr. Chem. Lett. 2021, 10, 9.

    Article  Google Scholar 

  17. Mirosław, B.; Babyuk, D.; Łapczuk-Krygier, A.; Kacka-Zych, A.; Demchuk, O. M.; Jasiński, R. Monatsh. Chem. 2018, 149, 1877.

    Google Scholar 

  18. Sedenkova, K. N.; Andriasov, K. S.; Eremenko, M. G.; Grishin, Y. K.; Alferova, V. A.; Baranova, A. A.; Zefirov, N. A.; Zefirova, O. N.; Zarubaev, V. V.; Gracheva, Y. A.; Milaeva, E. R.; Averina, E. B. Molecules 2022, 27, 3546.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  19. Jasiński, R. Coll. Czech. Chem. Commun. 2009, 74, 1341.

    Article  Google Scholar 

  20. Dresler, E.; Jasiński, R. Przem. Chem. 2015, 94 2244.

    CAS  Google Scholar 

  21. Jasiński, R. Tetrahedron Lett. 2015, 56, 532.

    Article  Google Scholar 

  22. Jasiński, R.; Ziółkowska, M.; Demchuk, O. M.; Maziarka, A. Cent. Eur. J. Chem. 2014, 12, 586.

    Google Scholar 

  23. Zawadzińska, K.; Gadocha, Z.; Pabian, K.; Wróblewska, A.; Wielgus, E.; Jasiński, R. Materials 2022, 15, 7584.

    Article  PubMed  PubMed Central  Google Scholar 

  24. Fryźlewicz, A.; Łapczuk-Krygier, A.; Kula, K.; Demchuk, O. M.; Dresler, E.; Jasiński, R. Chem. Heterocycl. Compd. 2020, 56, 120.

    Article  Google Scholar 

  25. Kras, J.; Woliński, R.; Naghatsky, R.; Demchuk, O. M.; Jasiński, R. Molecules 2023, 28, 3535.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  26. Iwai, K.; Wada, K.; Nishiwaki, N. Molecules 2022, 27, 4804.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  27. Jasiński, R.; Mróz, K.; Kącka, A. J. Heterocycl. Chem. 2016, 53, 1424.

    Article  Google Scholar 

  28. Jasiński, R.; Mróz, K. React. Kinet., Mech. Catal. 2015, 116, 35.

  29. Kula, K.; Sadowski, M. Chem. Heterocycl. Compd. 2023, 59, 138.

    Article  CAS  Google Scholar 

  30. Kras, J.; Wróblewska, A.; Kącka-Zych, A. Sci. Radices 2023, 2, 112.

    Article  Google Scholar 

  31. Woliński, P.; Kącka-Zych, A.; Dziuk, B.; Ejsmont, K.; Łapczuk-Krygier, A.; Dresler, E. T. J. Mol. Struct. 2019, 1192, 27.

    Article  Google Scholar 

  32. Domingo, L. R.; Aurell, M. J.; Pérez, P. Tetrahedron 2014, 20, 4519.

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Radomir Jasiński.

Additional information

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2023, 59(11/12), 730–732

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Jasiński, R. Recent progress in the synthesis of nitroisoxazoles and their hydrogenated analogs via [3+2] cycloaddition reactions (microreview). Chem Heterocycl Comp 59, 730–732 (2023). https://doi.org/10.1007/s10593-024-03262-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-024-03262-x

Navigation