Skip to main content
SpringerLink
Log in

Synthesis, Structure, and Keto-Enol Tautomerism of 3-R1-5,5-R2,R2-6-R3-2,3,5,6-Tetrahydropyran-2,4-diones

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

Abstract

Ethyl esters of 2,4-dibromo-2-R1-4-R2-3-oxopentanoic and -hexanoic acids react with zinc and aliphatic or aromatic aldehydes under the conditions of the Reformatskii reaction to give 3-R1-5,5-R2, R2-6-R3-2,3,5,6-tetrahydropyran-2,4-diones, which are obtained in three forms: keto, enol with enolization of the keto group, and enol with enolization of the ester group. The keto form is isolated by crystallization from a mixture of CCl4 and petroleum ether; the first enol form, from MeOH, EtOH, and polar aprotic solvents; and the second enol form, from CHCl3. The second enol form is oxidized in DMSO to form a keto compound containing a hydroxy group at the 3-position of the heteroring.

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. Hagiwara, H. and Uda, H., J. Chem. Soc., Perkin Trans. 1, 1985, no. 6, p. 1157.

  2. Kashihara, H., Shinoki, H., Suemune, H., and Sakai, K., Chem. Pharm. Bull., 1986, vol. 34, no.11, p. 4527.

    CAS  Google Scholar 

  3. Ayer, W.A., Villar, J.D.F., and Migaj, B.S., Can. J. Chem., 1988, vol. 66, no.3, p. 506.

    CAS  Google Scholar 

  4. Tanabe, Y., Miyakado, M., Ohno, N., and Yoshioka, H., Chem. Lett., 1982, no. 10, p. 1543.

  5. Bacardit, R. and Moreno-Manas, M., Tetrahedron Lett., 1980, vol. 21, no.6, p. 551.

    Article  CAS  Google Scholar 

  6. Angelo, J. and Gomez-Pardo, D., Tetrahedron Lett., 1991, vol. 32, no.26, p. 3063.

    Google Scholar 

  7. Sugita, Y., Sakaki, J., Sato, M., and Kaneko, C., J. Chem. Soc., Perkin Trans. 1, 1992, no. 21, p. 2855.

  8. Tait, B.D., Hagen, S., Domagala, J., Ellsworth, E.L., Gajda, C., Hamilton, H., Vara, P.J.V.N., Ferguson, D., Graham, N., Hupe, D., Nouhan, C., Tummino, P.J., Humblet, C., Lunney, E.A., Pavlovsky, A., Rubin, J., Grachek, S.J., Baldwin, E.T., Bhat, T.N., Erickson, J.W., Gulnik, S.V., and Liu, B., J. Med. Chem., 1997, vol. 40, no.23, p. 3781.

    Article  CAS  Google Scholar 

  9. Shchepin, V.V., Sazhneva, Yu.Kh., Russkikh, N.Yu., and Vakhrin, M.I., Zh. Org. Khim., 2001, vol. 37, no.10, p. 1580.

    Google Scholar 

  10. Shchepin, V.V., Russkikh, N.Yu., and Sazhneva, Yu.Kh., Khim. Geterotsikl. Soedin., 2003, no. 2, p. 300.

  11. Shchepin, V.V., Sazhneva, Yu.Kh., Russkikh, N.Yu., and Vakhrin, M.I., Zh. Obshch. Khim., 2003, vol. 73, no.5, p. 804.

    Google Scholar 

  12. Shchepin, V.V., Sazhneva, Yu.Kh., Bagara, M.V., and Russkikh, N.Yu., Zh. Obshch. Khim., 2003, vol. 73, no.8, p. 1336.

    Google Scholar 

  13. Shchepin, V.V., Sazhneva, Yu.Kh., Russkikh, N.Yu., and Litvinov, D.N., Zh. Org. Khim., 2000, vol. 36, no.6, p. 808.

    Google Scholar 

  14. Castellino, S. and Sims, J.J., Tetrahedron Lett., 1984, vol. 25, no.22, p. 2307.

    Article  CAS  Google Scholar 

  15. Willson, T.M., Kocienski, P., Jarowicki, K., Isaac, K., Hitchock, P.M., Faller, A., and Campbell, S.F., Tetrahedron, 1990, vol. 46, no.5, p. 1767.

    CAS  ISI  Google Scholar 

  16. Wulferding, A., Jankowski, J.H., and Hoffman, M.R., Chem. Ber., 1994, vol. 127, no.7, p. 1275.

    CAS  Google Scholar 

  17. Fieser, L.F. and Fieser, M., Reagents for Organic Synthesis, New York: Wiley, 1967. Translated under the title Reagenty dlya organicheskogo sinteza, Moscow: Mir, 1970, vol. 1, p. 327.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Perm State University, Perm, Russia

    V. V. Shchepin, Yu. Kh. Sazhneva & N. Yu. Russkikh

  2. Institute of Organic Synthesis, Ural Division, Russian Academy of Sciences, Yekaterinburg, Russia

    M. I. Kodess

Authors
  1. V. V. Shchepin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. I. Kodess
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yu. Kh. Sazhneva
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. N. Yu. Russkikh
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

__________

Translated from Zhurnal Obshchei Khimii, Vol. 75, No. 10, 2005, pp. 1699–1704.

Original Russian Text Copyright © 2005 by Shchepin, Kodess, Sazhneva, Russkikh.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Shchepin, V.V., Kodess, M.I., Sazhneva, Y.K. et al. Synthesis, Structure, and Keto-Enol Tautomerism of 3-R1-5,5-R2,R2-6-R3-2,3,5,6-Tetrahydropyran-2,4-diones. Russ J Gen Chem 75, 1622–1627 (2005). https://doi.org/10.1007/s11176-005-0477-6

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11176-005-0477-6

Keywords

Search

Navigation