Skip to main content

Advertisement

SpringerLink
Log in

Synthesis of 5-ethynylisoxazoles based on 1,3-dipolar cycloaddition reactions of nitrile oxides with conjugated diynes

  • Brief Communications
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

New 5-ethynylisoxazoles were obtained via 1,3-dipolar cycloaddition reactions of nitrile oxides with buta-1,3-diynes. The cycloaddition proceeds regioselectively by the terminal triple bond.

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

References

  1. J. Zhu, J. Mo, H. Lin, Y. Chen, H. Sun, Bioorg. Med. Chem., 2018, 26, 3065; DOI: https://doi.org/10.1016/j.bmc.2018.05.013.

    Article  CAS  PubMed  Google Scholar 

  2. A. Thakur, M. Verma, R. Bharti, R. Sharma, Tetrahedron, 2022, 119, 132813; DOI: https://doi.org/10.1016/j.tet.2022.132813.

    Article  CAS  Google Scholar 

  3. D. X. Duc, V. C. Dung, Curr. Org. Chem., 2021, 25, 2938; DOI: https://doi.org/10.2174/1385272825666211118104213.

    Article  CAS  Google Scholar 

  4. J. Zhu, J. Mo, H. Lin, Y. Chen, H. Sun, Bioorg. Med. Chem., 2018, 26, 3065; DOI: https://doi.org/10.1016/j.bmc.2018.05.013.

    Article  CAS  PubMed  Google Scholar 

  5. J. Sun, C. Lin, X. Qin, X. Dong, Z. Tu, F. Tang, C. Chen, J. Zhang, Bioorg. Med. Chem. Lett., 2015, 25, 3129; DOI: https://doi.org/10.1016/j.bmcl.2015.06.009.

    Article  CAS  PubMed  Google Scholar 

  6. H. Ananda, K. S. Sharath Kumar, M. Hegde, K. S. Rangappa, Mol. Cell. Biochem., 2016, 420, 141; DOI: https://doi.org/10.1007/s11010-016-2777-z.

    Article  CAS  PubMed  Google Scholar 

  7. S. Y. Sharp, C. Prodromou, P. Workman, K. Boxall, M. V. Powers, J. L. Holmes, G. Box, T. P. Matthews, K.-M. J. Cheung, A. Kalusa, K. James, A. Hayes, A. Hardcastle, B. Dymock, P. A. Brough, X. Barril, J. E. Cansfield, L. Wright, A. Surgenor, N. Foloppe, R. E. Hubbard, W. Aherne, L. Pearl; K. Jones, E. McDonald, F. Raynaud, S. Eccles, M. Drysdale, P. Workman, Mol. Cancer. Ther., 2007, 6, 1198; DOI: https://doi.org/10.1158/1535-7163.MCT-07-0149.

    Article  CAS  PubMed  Google Scholar 

  8. Y. Ono, T. Hirao, T. Ikeda, T. Haino, J. Org. Chem., 2021, 86, 5499; DOI: https://doi.org/10.1021/acs.joc.0c03005.

    Article  CAS  PubMed  Google Scholar 

  9. S. Sahoo, S. Pal, J. Org. Chem., 2021, 86, 4081; DOI: https://doi.org/10.1021/acs.joc.0c02926.

    Article  CAS  PubMed  Google Scholar 

  10. Y. Tian, X. Li, D. Yin, Chem. Commun., 2019, 55, 12865; DOI: https://doi.org/10.1039/C9CC06769H.

    Article  CAS  Google Scholar 

  11. Y. Yamada, H. Takashima, D. L. Walmsley, F. Ushiyama, Y. Matsuda, H. Kanazawa, T. Yamaguchi-Sasaki, N. Tanaka-Yamamoto, J. Yamagishi, R. Kurimoto-Tsuruta, Y. Ogata, N. Ohtake, H. Angove, L. Baker, R. Harris, A. Macias, A. Robertson, A. Surgenor, H. Watanabe, K. Nakano, M. Mima, K. Iwamoto, A. Okada, I. Takata, K. Hitaka, A. Tanaka, K. Fujita, H. Sugiyama, R. E. Hubbard, J. Med. Chem., 2020, 63, 14805; DOI: https://doi.org/10.1021/acs.jmedchem.0c01215.

    Article  CAS  PubMed  Google Scholar 

  12. F. Ushiyama, H. Takashima, H. Sugiyama, Bioorg. Med. Chem., 2021, 30, 115964; DOI: https://doi.org/10.1016/j.bmc.2020.115964.

    Article  CAS  PubMed  Google Scholar 

  13. A. A. G. Fernandes, A. F. da Silva, C. Y. Okada Jr., V. Suzukawa, R. A. Cormanich, I. D. Jurberg, Eur. J. Org. Chem., 2019, 3022; DOI: https://doi.org/10.1002/ejoc.201900187.

  14. L. B. Sokolov, L. K. Vagina, V. N. Chistokletov, A. A. Petrov, Zhurn. Org. Khimii, 1966, 2, 615 (in Russian).

    CAS  Google Scholar 

  15. G. Himbert, D. Faul, M. Barz, Z. Naturforsch., B, 1991, 46, 955; DOI: https://doi.org/10.1515/znb-1991-0715.

    Article  CAS  Google Scholar 

  16. Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis. Novel Strategies in Synthesis, Ed. H. Feier, Wiley, New York, 2008, 1–127.

    Google Scholar 

  17. Synthetic Application of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products, Eds A. Padwa, W. H. Pearson, Wiley, New York, 2002, 361–472.

    Google Scholar 

  18. A. P. Molchanov, M. M. Efremova, M. A. Kuznetsov, Russ. Chem. Bull., 2022, 71, 620; DOI: https://doi.org/10.1007/s11172-022-3460-z.

    Article  CAS  Google Scholar 

  19. X. Duan, N. Zheng, M. Li, X. Sun, Z. Lin, P. Qiu, W. Song, Chin. Chem. Lett., 2021, 32, 4019; DOI: https://doi.org/10.1016/j.cclet.2021.05.037.

    Article  CAS  Google Scholar 

  20. V. Fiandanese, S. Maurantonio, A. Punzi, G. G. Rafaschieri, Org. Biomol. Chem., 2012, 10, 1186; DOI: https://doi.org/10.1039/c1ob06701j.

    Article  CAS  PubMed  Google Scholar 

  21. A. I. Govdi, N. A. Danilkina, A. V. Ponomarev, I. A. Balova, J. Org. Chem., 2019, 84, 1925; DOI: https://doi.org/10.1021/acs.joc.8b02916.

    Article  CAS  PubMed  Google Scholar 

  22. M. M. Efremova, A. I. Govdi, V. V. Frolova, A. M. Rumyantsev, I. A. Balova, Molecules, 2021, 26, 2801; DOI: https://doi.org/10.3390/molecules26092801.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  23. M. A. Topchiy, G. K. Sterligov, A. A. Ageshina, S. A. Rzhevskiy, L. I. Minaeva, M. S. Nechaev, A. F. Asachenko, Russ. Chem. Bull., 2022, 71, 484; DOI: https://doi.org/10.1007/s11172-022-3437-y.

    Article  CAS  Google Scholar 

  24. I. A. Volynkina, Y. V. Zakalyukina, V. A. Alferova, A. R. Belik, D. K. Yagoda, A. A. Nikandrova, Y. A. Buyuklyan, A. V. Udalov, E. V. Golovin, M. A. Kryakvin, D. A. Lukianov, M. V. Biryukov, P. V. Sergiev, O. A. DontsovaIlya, A. Osterman, Antibiotics (Basel), 2022, 11, 1198. DOI: https://doi.org/10.3390/antibiotics11091198.

    Article  CAS  PubMed  Google Scholar 

  25. T. Slagbrand, G. Kervefors, F. Tinnis, H. Adolfsson, Adv. Synth. Catal., 2017, 359, 1990; DOI: https://doi.org/10.1002/adsc.201700154.

    Article  CAS  Google Scholar 

  26. A. P. Kozikowski, M. Adamczyk, J. Org. Chem., 1983, 48, 366; DOI: https://doi.org/10.1021/jo00151a017.

    Article  CAS  Google Scholar 

  27. M. Vadivelu, S. Sampath, K. Muthu, K. Karthikeyan, C. Praveen, J. Org. Chem., 2019, 84, 13636; DOI: https://doi.org/10.1021/acs.joc.9b01896.

    Article  CAS  PubMed  Google Scholar 

  28. T. Baba, T. Ara, M. Hasegawa, Y. Takai, Y. Okumura, M. Baba, K. A. Datsenko, M. Tomita, B. L. Wanner, H. Mori, Mol. Syst. Biol., 2006, 2, 2006.0008; DOI: https://doi.org/10.1038/msb4100050.

    Article  PubMed Central  Google Scholar 

  29. N. S. Sánchez, M. Königsberg, Biochem. Mol. Biol. Educ., 2006, 34, 209; DOI: https://doi.org/10.1002/bmb.2006.49403403209.

    Article  PubMed  Google Scholar 

  30. J. van Meerloo, G. J. Kaspers, J. Cloos, Methods Mol. Biol., 2011, 731, 237; DOI: https://doi.org/10.1007/978-1-61779-080-5_20.

    Article  CAS  PubMed  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. St. Petersburg State University, 7/9 Universitetskaya nab., 199034, St. Petersburg, Russian Federation

    M. M. Efremova, A. M. Rumyantsev, E. S. Babitova, T. M. Ianshina & A. I. Govdi

Authors
  1. M. M. Efremova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. M. Rumyantsev
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. E. S. Babitova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. T. M. Ianshina
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. A. I. Govdi
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. I. Govdi.

Additional information

Dedicated to the 300th anniversary of the St. Petersburg State University.

The studies were carried out using the equipment of the resource centers of St. Petersburg State University “Magnetic Resonance Research Center”, “Chemical Analysis and Materials Research Center”.

The study was financially supported by the Russian Science Foundation (Project No. 19-73-10077-Π).

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, Vol. 72, No. 7, pp. 1717–1721, July, 2023.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Efremova, M.M., Rumyantsev, A.M., Babitova, E.S. et al. Synthesis of 5-ethynylisoxazoles based on 1,3-dipolar cycloaddition reactions of nitrile oxides with conjugated diynes. Russ Chem Bull 72, 1717–1721 (2023). https://doi.org/10.1007/s11172-023-3952-5

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-023-3952-5

Key words

Search

Navigation