Skip to main content
SpringerLink
Log in

One-pot stereoselective tandem assembly of functionalized furan-3(2H)-one from γ-hydroxyalk-2-ynenitriles and 3-hydroxybenzoic acid

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

Abstract

γ-Hydroxyalk-2-ynenitriles react chemo-, regio-, and stereoselectively with 3-hydroxybenzoic acid under mild conditions (Et3N, MeCN, 20–25°C, 48–144 h) giving 4-oxo-2-{3-[(1Z)-(1-cyanoalk-1-en-2-yl)oxy]-phenyl}-4,5-dihydrofuran-3-carbonitriles in 60–75% yields. The reaction opens a simple path to a new group of furan-3(2H)-one derivatives with pharmacophore functions.

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

Similar content being viewed by others

References

  1. Crone, B. and Kirsch, S.F., J. Org. Chem., 2007, vol. 72, p. 5435.

    Article  CAS  Google Scholar 

  2. Li, Y. and Hale, K.J., Org. Lett., 2007, vol. 9, p. 1267.

    Article  CAS  Google Scholar 

  3. Ishikawa, M. and Ninomiya, T., J. Antibiot., 2008, vol. 61, p. 692.

    Article  CAS  Google Scholar 

  4. Haung, T.T. and Kirsch, S.F., Synthesis and Chemistry of 3(2H)-Furanones. In Targets in Heterocyclic Systems: Chemistry and Properties, Attanasi, O.A. and Spinelli, D., Eds., Rome: Societa Chimica Italiana, 2009, vol. 13.

    Google Scholar 

  5. Chimichi, S., Boccalini, M., Salvador, A., Dall’Acqua, F., Basso, G., and Viola, G., Chem. Med. Chem., 2009, vol. 4, p. 769.

    Article  CAS  Google Scholar 

  6. Ishikawa, M., Ninomiya, T., Akabane, H., Kushida, N., Tsujiuchi, G., Ohyama, M., Gomi, S., Shito, K., and Murata, T., Bioorg. Med. Chem. Lett., 2009, vol. 19, p. 1457.

    Article  CAS  Google Scholar 

  7. Egi, M., Azechi, K., Saneto, M., Shimizu, K., and Akai, S., J. Org. Chem., 2010, vol. 75, p. 2123.

    Article  CAS  Google Scholar 

  8. Poonoth, M. and Krause, N., J. Org. Chem., 2011, vol. 76, p. 1934.

    Article  CAS  Google Scholar 

  9. Pertino, M., Schmeda-Hirschmann, G., Santos, L.S., Rodríguez, J.A., and Theoduloz, C., Z. Naturforsch., 2007, vol. 62b, p. 275.

    Google Scholar 

  10. Felman, S.W., Jirkovsky, I., Memoli, K.A., Borella, L., Wells, C., Russell, J., and Ward, J., J. Med. Chem., 1992, vol. 35, p. 1183.

    Article  CAS  Google Scholar 

  11. Silverstein, F.E., Faich, G., Goldstein, J.L., Simon, L.S., Pincus, T., Whelton, A., Makuch, R., Eisen, G., Agrawal, N.M., Stenson, W.F., Burr, A.M., Zhao, W.W., Kent, J.D., Lefkowith, J.B., Verburg, K.M., and Geis, G.S., J. Am. Med. Assoc., 2000, vol. 284, p. 1247.

    Article  CAS  Google Scholar 

  12. Shin, S.S., Byun, Y., Lim, K.M., Choi, J.K., Lee, K.-W., Moh, J.H., Kim, J.K., Jeong, Y.S., Kim, J.Y., Choi, Y.H., Koh, H.-J., Park, Y.-H., Oh, Y.I., Noh, M.-S., and Chung, S., J. Med. Chem., 2004, vol. 47, p. 792.

    Article  CAS  Google Scholar 

  13. Sasaki, T., Yamakoshi, J., Saito, M., Kasai, K., Matsudo, T., Koga, T., and Mori, K., Biosci. Biotechnol. Biochem., 1998, vol. 62, p. 1865.

    Article  CAS  Google Scholar 

  14. Sasaki, T., Yamakoshi, J., Saito, M., Kasai, K., Matsudo, T., Kikuchi, M., Koga, T., and Mori, K., Biosci. Biotechnol. Biochem., 1998, vol. 62, p. 2145.

    Article  CAS  Google Scholar 

  15. Jung, J.-K., Semple, G., and Johnson, B.R., US Patent no. 7803837 B2, 2010.

  16. Qi, C., Jiang, H., Huang, L., Yuan, G., and Ren, Y., Org. Lett., 2011, vol. 13, p. 5520.

    Article  CAS  Google Scholar 

  17. Amslinger, S. and Linder, S.K., Synthesis, 2011, vol. 16, p. 2671.

    Article  Google Scholar 

  18. Trofimov, B.A., Shemyakina, O.A., Mal’kina, A.G., Ushakov, I.A., Kazheva, O.N., Alexandrov, G.G., and Dyachenko, O.A., Org. Lett., 2010, vol. 12, p. 3200.

    Article  CAS  Google Scholar 

  19. Shemyakina, O.A., Mal’kina, A.G., Nosyreva, V.V., Ushakov, I.A., and Trofimov, B.A., Arkivoc, 2012, vol. viii, p. 319.

    Article  Google Scholar 

  20. Mal’kina, A.G., Volostnykh, O.G., Petrushenko, K.B., Shemyakina, O.A., Nosyreva, V.V., Ushakov, I.A., and Trofimov, B.A., Tetrahedron, 2013, vol. 69, p. 3714.

    Article  Google Scholar 

  21. Mal’kina, A.G., Volostnykh, O.G., Stepanov, A.V., Ushakov, I.A., Petrushenko, K.B., and Trofimov, B.A., Synthesis, 2013, vol. 45, p. 3435.

    Article  Google Scholar 

  22. Landor, S.R., Demetriou, B., Grzeskowiak, R., and Pavey, D., J. Organometal. Chem., 1975, vol. 93, p. 129.

    Article  CAS  Google Scholar 

  23. Trofimov, B.A., Andriyankova, L.V., Shaikhudinova, S.I., Kazantseva, T.I., Mal’kina, A.G., and Afonin, A.V., Synthesis, 2002, vol. 7, p. 853.

    Article  Google Scholar 

  24. Miller, S.I. and Tanaka, R., Selective Organic Transformation, Thyagarajab, B.S., Ed., New York: Wiley-Interscience, 1978, vol. 1.

  25. Dickstein, J.I. and Miller, S.I., The Chemistry of the Carbon-Carbon Triple Bond, Patai, S., Ed., New York: Wiley, 1978, vol. 2, p. 814.

Download references

Author information

Authors and Affiliations

  1. Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, Irkutsk, 664033, Russia

    O. A. Shemyakina, A. V. Stepanov, O. G. Volostnykh, A. G. Mal’kina, I. A. Ushakov & B. A. Trofimov

Authors
  1. O. A. Shemyakina
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. V. Stepanov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. O. G. Volostnykh
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. G. Mal’kina
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. I. A. Ushakov
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. B. A. Trofimov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to B. A. Trofimov.

Additional information

Original Russian Text © O.A. Shemyakina, A.V. Stepanov, O.G. Volostnykh, A.G. Mal’kina, I.A. Ushakov, B.A. Trofimov, 2014, published in Zhurnal Organicheskoi Khimii, 2014, Vol. 50, No. 11, pp. 1631–1634.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Shemyakina, O.A., Stepanov, A.V., Volostnykh, O.G. et al. One-pot stereoselective tandem assembly of functionalized furan-3(2H)-one from γ-hydroxyalk-2-ynenitriles and 3-hydroxybenzoic acid. Russ J Org Chem 50, 1617–1620 (2014). https://doi.org/10.1134/S107042801411013X

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S107042801411013X

Keywords

Search

Navigation