Skip to main content
Log in

Synthesis of 3- and 5-Alkyl-6-alkyl(aryl)tetrahydropyran-2,4-diones by the Condensation of β-Oxo Acid Esters with Aldehydes and Ketones

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

A method is proposed for obtaining 3- and 5-alkyl-6-alkyl(aryl)tetrahydropyran-2,4-diones based on the condensation of the dianion of alkyl(dialkyl)acetoacetic ester with aldehydes and ketones.

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. E. F. Steinmetz, Piper methysticum (Kava), Famous Drug Plant of the South Sea Islands, Elsevier, Amsterdam (1960).

    Google Scholar 

  2. W. B. Morc, M. T. Magalhaes, and O. R. Gottlieb in L. Zechmeister (editor), Progress in the Chemistry of Organic Natural Products, Vol. 20, Springer-Verlag, Berlin (1962).

    Google Scholar 

  3. B. Eistert and G. Heck, Justus Liebigs Ann. Chem., 681, 123 (1965).

    Google Scholar 

  4. R. M. Carlson, A. R. Oyler, and J. R. Peterson, J. Org. Chem., 40, 1610 (1975).

    Google Scholar 

  5. A. A. Akhrem, F. A. Lakhvich, L. G. Lis, V. A. Khripach, N. A. Fil'genkov, V. A. Kozinets, and F. S. Pashkovskii, Dokl. Akad. Nauk SSSR, 311, 1381 (1990).

    Google Scholar 

  6. J. M. McIntosh and P. M. Beaumier, Can. J. Chem., 51, 843 (1979).

    Google Scholar 

  7. H. Stetter and W. Dierichs, Chem. Ber., 85, 1061 (1952).

    Google Scholar 

  8. H. O. House, Modern Synthetic Reactions, Benjamin, New York (1972). p. 511.

    Google Scholar 

  9. D. N. Kursanov, Z. N. Parnes, M. I. Kalinkin, and N. M. Loim, Ionic Hydrogenation[in Russian], Khimiya, Moscow (1979), p. 192.

    Google Scholar 

  10. M. W. Rathke and J. Deitch, Tetrahedron Lett., 2953 (1971).

  11. I. Shahak and Y. Sasson, Tetrahedron Lett., 4207 (1973).

  12. R. M. Carlson and J. L. Isidor, Tetrahedron Lett., 4819 (1973).

  13. S. N. Huckin and L. Weiler, Tetrahedron Lett., 1082 (1974).

  14. M. Sato, J. Sakaki, K. Takayama, S. Kobayashi, M. Suzuki, and C. Kaneko, Chem. Pharm. Bull., 38, 94 (1990).

    Google Scholar 

  15. J. R. Petersen, T. J. Winter, and C. P. Miller, Synth. Commun., 18, 949 (1988).

    Google Scholar 

  16. I. Paterson, D. J. Wallace, and C. J. Cowden, Synthesis, 639 (1998).

  17. D. Seebach and K. Meyer, Angew. Chem., 86, 40 (1974).

    Google Scholar 

  18. T. Reffstrup and P. M. Boll, Acta Chem. Scand., B30, 613 (1976).

    Google Scholar 

  19. J. F. Wolfe, T. M. Harris, and C. R. Hauser, J. Org. Chem., 29, 3249 (1964).

    Google Scholar 

  20. Organicum[Russian translation], Vol. 2, Mir, Moscow (1979), p. 176.

  21. M. Sato, H. Ogasawara, K. Oi, and T. Kato, Chem. Pharm. Bull., 31, 1896 (1983).

    Google Scholar 

  22. C. Pouchert, Alrich Library of NMR SpectraEd. 2, Vol. 2, Aldrich Chem. Co. Inc. (1983), p. 53D; Aldrich Library of IR Spectra, Ed. 3, Aldrich Chem. Co. Inc. (1981), p. 852D.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Lokot', I.P., Pashkovskii, F.S. & Lakhvich, F.A. Synthesis of 3- and 5-Alkyl-6-alkyl(aryl)tetrahydropyran-2,4-diones by the Condensation of β-Oxo Acid Esters with Aldehydes and Ketones. Chemistry of Heterocyclic Compounds 37, 707–714 (2001). https://doi.org/10.1023/A:1011913328785

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1011913328785

Navigation