Skip to main content
SpringerLink
Log in

Reaction of 2- and 4-vinylpyridines with phenacylpyridinium ylids

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The reaction of 2- and 4-vinylpyridines with 3-substituted phenacylpyridinium ylids takes place regioselectively with the formation of only 6-substituted 1-pyridyl-3-aroylindolizines. The reaction of the same ylids with dimethyl acetylenedicarboxylate gives a mixture of isomeric 6- and 8-substituted 1,2-dicarbomethoxy-3-aroylindolizines. In the analogous reaction of 2-bromo-1-phenacyl-pyridinium ylid, in addition to the corresponding 5-bromoindolizine, the product of its spontaneous cyclization, viz., 4,5-dicarbomethoxy-6-oxo-(6H)-10c-azaacephenanthrylene, was isolated.

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. P. B. Terent'ev, S. M. Vinogradova, A. N. Kost, and A. G. Strukovskii, Khim. Geterotsikl. Soedin., No. 1, 64 (1973).

    Google Scholar 

  2. F. Fröhlich and F. Kröhnke, Ber.,104, 1621 (1971).

    Google Scholar 

  3. A. D. Harsch, S. Johnson, and D. W. Boykin, Chem. Commun., No. 4, 119 (1977).

    Google Scholar 

  4. M. H. Palmer, The Structure and Reactions of Heterocyclic Compounds, Arnold, London (1967), p. 305.

    Google Scholar 

  5. C. A. Henrick, E. Ritchie, and W. C. Taylor, Austral. J. Chem.,20, 2455 (1967).

    Google Scholar 

  6. L. A. Aslanov, V. M. Ionov, V. A. Tafeenko, S. Akhmed Farang, A. N. Kost, P. B. Terent'ev, and S. M. Vinogradova, Zh. Struk. Khim.,17, 746 (1976).

    Google Scholar 

  7. L. Fieser and M. Fieser, Current Topics in Organic Chemistry, Vol. 1, Van Nostrand Reinhold (1964).

  8. I. Tamura, I. Sumida, I. Miku, and M. Ikeda, J. Chem. Soc., Perkin Trans. I, No. 5, 406 (1975).

    Google Scholar 

  9. L. Bellamy, The Infrared Spectra of Complex Molecules, Halsted Press (1975).

  10. P. B. Terent'ev, S. M. Vinogradova, and A. N. Kost, Khim. Geterotsikl. Soedin., No. 4, 509 (1975).

    Google Scholar 

  11. F. Kröhnke, Ber.,68, 1177 (1935).

    Google Scholar 

  12. W. G. Phillips and K. W. Ratts, J. Org. Chem.,35, 3144 (1970).

    Google Scholar 

  13. F. Kröhnke and W. Hiffe, Ber.,70, 864 (1937).

    Google Scholar 

  14. C. A. Henrick, E. Ritchie, and W. C. Taylor, Austral. J. Chem.,20, 2467 (1967).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. M. V. Lomonosov Moscow State University, 117234, Moscow

    P. B. Terent'ev, S. M. Vinogradova & A. N. Kost

Authors
  1. P. B. Terent'ev
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. M. Vinogradova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. N. Kost
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Deceased.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 651–656, May, 1980.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Terent'ev, P.B., Vinogradova, S.M. & Kost, A.N. Reaction of 2- and 4-vinylpyridines with phenacylpyridinium ylids. Chem Heterocycl Compd 16, 506–511 (1980). https://doi.org/10.1007/BF00561349

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00561349

Keywords

Search

Navigation