Skip to main content
SpringerLink
Log in

Acetyldihydropyran Semicarbazones: Two-Step Diastereoselective Synthesis from Acetylene

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

2-Acetyl-3,4-dihydropyrans were synthesized in one step by diastereoselective reaction of acetylene with aromatic ketones, and their condensation with semicarbazide hydrochloride afforded the corresponding (E)-semicarbazones with high stereoselectivity in up to 86% yield.

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

Scheme
Scheme
Scheme
Scheme
Scheme

REFERENCES

  1. Rodygin, K.S., Werner, G., Kucherov, F.A., and Anani­kov, V.P., Chem. Asian J., 2016, vol. 11, p. 965. https://doi.org/10.1002/asia.201501323

    Article  CAS  PubMed  Google Scholar 

  2. Voronin, V.V., Ledovskaya, M.S., Bogachenkov, A.S., Rodygin, K.S., and Ananikov, V.P., Molecules, 2018, vol. 23, article no. 2442. https://doi.org/10.3390/molecules23102442

  3. Trofimov, B.A. and Schmidt, E.Yu., Acc. Chem. Res., 2018, vol. 51, p. 1117. https://doi.org/10.1021/acs.accounts.7b00618

    Article  CAS  PubMed  Google Scholar 

  4. Shmidt, E.Yu. and Trofimov, B.A., Dokl. Chem., 2022, vol. 505, p. 127. https://doi.org/10.1134/S0012500822700069

    Article  Google Scholar 

  5. Schmidt, E.Yu., Trofimov, B.A., Zorina, N.V., Mikha­le­va, A.I., Ushakov, I.A., Skital’tseva, E.V., Kazhe­va, O.N., Alexandrov, G.G., and Dyachenko, O.A., Eur. J. Org. Chem., 2010, vol. 2010, p. 6727. https://doi.org/10.1002/ejoc.201001229

    Article  CAS  Google Scholar 

  6. Afonin, A.V., Ushakov, I.A., Tarasova, O.A., Shmidt, E.Yu., Mikhaleva, A.I., and Voronov, V.K., Russ. J. Org. Chem., 2000, vol. 36, p. 1777.

    CAS  Google Scholar 

  7. Venkatachalam, T.K., Bernhardt, P.V., Noble, Ch.J., Fletcher, N., Pierens, G.K., Thurecht, K.J., and Reutens, D.C., J. Inorg. Biochem., 2016, vol. 162, p. 295. https://doi.org/10.1016/j.jinorgbio.2016.04.006

    Article  CAS  PubMed  Google Scholar 

  8. Jaiswal, Sh., Akhilesh, Uniyal, A., Tiwari, V., and Ayyannan, S.R., Bioorg. Med. Chem., 2022, vol. 60, article ID 116698. https://doi.org/10.1016/j.bmc.2022.116698

  9. Rajmohan, G., Shanmugam, R., Elangovan, A., Ravindran, G., Sangeetha, T., and Arivazhagan, G., Mater. Today Proc., 2022, vol. 60, p. 1310. https://doi.org/10.1016/j.matpr.2021.09.305

    Article  CAS  Google Scholar 

  10. Cocco, M.T., Cogiv, C., Onnis, V., Pellerano, M.L., and de Logu, A., Bioorg. Med. Chem., 2002, vol. 10, p. 501. https://doi.org/10.1016/S0968-0896(01)00310-8

    Article  CAS  PubMed  Google Scholar 

  11. Jia, X., Liu, Q., Wang, Sh., Zeng, B., Du, G., Zhang, Ch., and Li, Y., Bioorg. Med. Chem., 2020, vol. 28, article ID 115557. https://doi.org/10.1016/j.bmc.2020.115557

  12. Pósa, V., Hajdu, B., Tóth, G., Dömötör, O., Kowol, Ch.R., Keppler, B.K., Spengler, G., Gyurcsik, B., and Enyedy, É.A., J. Inorg. Biochem., 2022, vol. 231, article ID 111786. https://doi.org/10.1016/j.jinorgbio.2022.111786

  13. Kumar, S., Malachowski, W.P., DuHadaway, J.B., LaLonde, J.M., Carroll, P.J., Jaller, D., Metz, R., Prendergast, G.C., and Muller, A.J., J. Med. Chem., 2008, vol. 51, p. 1706. https://doi.org/10.1021/jm7014155

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  14. Yoo, N.H., Jang, D.S., Yoo, J.L., Lee, Y.M., Kim, Y.S., Cho, J.-H., and Kim, J.S., J. Nat. Prod., 2008, vol. 71, p. 713. https://doi.org/10.1021/np070489a

    Article  CAS  PubMed  Google Scholar 

  15. Cao, J., Yu, H., Wu, Y., and Wang, X., Mini–Rev. Med. Chem., 2019, vol. 19, p. 292. https://doi.org/10.2174/1389557518666181026091449

    Article  CAS  PubMed  Google Scholar 

  16. Desimoni, G., Faita, G., and Quadrelli, P., Chem. Rev., 2018, vol. 118, p. 2080. https://doi.org/10.1021/acs.chemrev.7b00322

    Article  CAS  PubMed  Google Scholar 

Download references

ACKNOWLEDGMENTS

This study was performed using the facilities of the Baikal joint analytical center, Siberian Branch, Russian Academy of Sciences.

Funding

This study was financially supported in the framework of state assignment no. 121021000199-6.

Author information

Authors and Affiliations

  1. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 664033, Irkutsk, Russia

    I. V. Tatarinova, N. A. Lobanova, I. A. Ushakov, E. Yu. Schmidt & B. A. Trofimov

  2. Angarsk State Technical University, 665835, Angarsk, Russia

    E. Yu. Schmidt

Authors
  1. I. V. Tatarinova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. N. A. Lobanova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. I. A. Ushakov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. E. Yu. Schmidt
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. B. A. Trofimov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to B. A. Trofimov.

Ethics declarations

The authors declare the absence of conflict of interest.

Additional information

Translated from Zhurnal Organicheskoi Khimii, 2023, Vol. 59, No. 3, pp. 405–410 https://doi.org/10.31857/S0514749223030126.

Dedicated to Full Member of the Russian Academy of Sciences I.P. Beletskaya on her jubilee.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Tatarinova, I.V., Lobanova, N.A., Ushakov, I.A. et al. Acetyldihydropyran Semicarbazones: Two-Step Diastereoselective Synthesis from Acetylene. Russ J Org Chem 59, 540–544 (2023). https://doi.org/10.1134/S1070428023030235

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428023030235

Keywords:

Search

Navigation