Skip to main content
SpringerLink
Log in

Investigation on pyran and related compounds

XLII The synthesis of 4-aminocoumarins and the mechanism of the replacement of the halogen in 4-chlorocoumarin

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

A convenient method for obtaining 4-aminocoumarins by the reaction of 4-chlorocoumarin with amines in dimethyl sulfoxide is proposed. The reactions of 4-chlorocoumarin with CD3ONa in CD3OD and with [N-D1]piperidine, of [3-D1]-4-chlorocoumarin with CH3ONa in CH3OH and with aniline and n-butylamine and of 4-methoxycoumarin with CD3ONa in CD3OD have been studied and the mechanism of nucleophilic and substitution in position 4 of the coumarin system is discussed.

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. V. A. Zagorevskii, V. L. Savel'ev, and N. V. Dudykina, ZhOrKh, 4, 2041 (1968).

    Google Scholar 

  2. V. A. Zagorevskii, V. L. Savel'ev,and N. V. Dudykina, KhGS [Chemistry of Heterocyclic Compounds], Collection 2, p. 155 (1970).

    Google Scholar 

  3. R. Anschütz, Ann., 367, 169 (1909).

    Google Scholar 

  4. J. F. Bunnet, Theoretical Organic Chemistry [Russian Translation], IL, Moscow, p. 190 (1963).

    Google Scholar 

  5. M. I. Rybinskaya, ZhVKhO, 12, 11 (1967).

    Google Scholar 

  6. D. P. Spalding, H. S. Mosher, and F. C. Whitmore, J. Am. Chem. Soc., 72, 5338 (1950).

    Google Scholar 

  7. A. R. Knight and J. S. McIntyre, Canad. J. Chem., 46, 1949 (1968).

    Google Scholar 

  8. V. A. Zagorevskii, V. L. Savel'ev, N. V. Dudykina, and S. L. Portnova, ZhOrKh 3, 568 (1967).

    Google Scholar 

  9. V. A. Zagorevskii, V. L. Savel'ev, L. M. Meshcheryakova, and V. G. Vinokurov, KhGS [Chemistry of Heterocyclic Compounds], Collection 2, p. 166 (1970).

    Google Scholar 

  10. V. A. Zagorevskii and V. L. Savel'ev, ZhOKh, 34, 2290 (1964).

    Google Scholar 

  11. V. A. Zagorevskii, Sh. M. Glozman, and L. A. Zhmurenko, KhGS [Chemistry of Heterocyclic Compounds], 6, 1015 (1970).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Pharmacology, Academy of Medical Sciences of the USSR, Moscow

    V. A. Zagorevskii, V. L. Savel'ev & L. M. Meshcheryakova

Authors
  1. V. A. Zagorevskii
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. L. Savel'ev
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. L. M. Meshcheryakova
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

For Communication XLI, see [11].

Translated from Khimiya Geterotsiklicheskikh Soedinenii, Vol. 6, No. 8, pp. 1019–1023, August, 1970.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Zagorevskii, V.A., Savel'ev, V.L. & Meshcheryakova, L.M. Investigation on pyran and related compounds. Chem Heterocycl Compd 6, 947–951 (1970). https://doi.org/10.1007/BF00480619

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00480619

Keywords

Search

Navigation