Skip to main content
SpringerLink
Log in

Synthesis and properties of 1-substituted derivatives of diethyl 4-aryl-1,4-dihydrcpyridine-3,5-dicarboxylic acid esters

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

1-Unsubstituted 4-aryl-3,5-diethoxycarbonyl-1,4-dihydropyridines in the presence of NaH form anions that react with alkyl halides, acid chlorides, and halo acid esters to form the corresponding 1-substituted derivatives of 1,4-dihydropyridine Hydrolysis of one or both ethoxycarbonyl groups in the 3 and 5 positions, as well as hydrolysis of ethyl 4-phenyl-3,5-diethoxycarbonyl-1,4-dihydropyridinyl-1-acetate, occur upon reaction with alkali, but 1,3,5-triethoxycarbonyl-4-phenyl-l,4-dihydropyridine gives the corresponding unsubstituted 1,4-dihydropyridine.

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

Literature cited

  1. F. Michell and H. Dralle, Lieb. Ann., 670, 57 (1963).

    Google Scholar 

  2. R. E. Lyle and D. A. Nelson, J. Org. Chem., 28, 169 (1963).

    Google Scholar 

  3. R. A. Dommisse and F. C. Alderweireldt, Bull. Soc. Chim. Belg., 82, 441 (1973).

    Google Scholar 

  4. A. É. Sausin', V. K. Lusis, G. Ya. Bubur, and Yu. I. Beilis, Khim. Geterotsikl. Soedin., No. 11, 1508 (1978).

    Google Scholar 

  5. J. Kuthan and J. Palaćek, Collect. Czech. Chem. Commun., 39, 3711 (1974).

    Google Scholar 

  6. A. M. Kats, V. V. Solov'eva, G. Ya. Dubur, and I. B. Mazheika, Izv. Akad. Nauk Latv. SSR, Ser. Khim., No. 6, 715 (1976).

    Google Scholar 

  7. T. Chennat and U. Eisner, J. Chem. Soc., Perkin Trans. I, No. 110, 926.

  8. M. Iwamami, T. Shibannuma, M. Fujimoto, R. Kawai, K. Tamizava, T. Takenaka, K. Takahasi, and M. Murakami, Chem. Pharm. Bull. Jpn., 27, 1426 (1979).

    Google Scholar 

  9. A. É. Sausin', V. K. Lusis, B. S. Chekavichus, and G. Ya. Dubur, Khim. Geterotsikl. Soedin., No. 2, 272 (1978).

    Google Scholar 

  10. K. N. Kilminster and M. Sainsburg, J. Chem. Soc., Perkin Trans. I, No. 18, 2269 (1972).

    Google Scholar 

  11. W. Steglich and G. Hoefle, Chem. Ber., 102, 1129 (1969).

    Google Scholar 

  12. P. I. Brignell, U. Eisner, and P. G. Farrell, J. Chem. Soc., B, No. 11, 1083 (1966).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Organic Synthesis, Academy of Sciences of the Latvian SSR, 226006, Riga

    V. K. Lusis & G. Ya. Dubur

Authors
  1. V. K. Lusis
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. G. Ya. Dubur
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1067–1071, August, 1982.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Lusis, V.K., Dubur, G.Y. Synthesis and properties of 1-substituted derivatives of diethyl 4-aryl-1,4-dihydrcpyridine-3,5-dicarboxylic acid esters. Chem Heterocycl Compd 18, 813–818 (1982). https://doi.org/10.1007/BF00506585

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00506585

Keywords

Search

Navigation