Skip to main content
SpringerLink
Log in

Indole derivatives

XCIX. Reaction of indoles with chloroacetic acids

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Indole and 2- and 5-substituted indoles react with both chloroacetic and dichlorolacetic acids to give 3-indolylacetic acids. Substitution of the pyrrole ring in the 1 and 3 positions hinders the reaction. The pathways of formation of heteroauxin from indole and chloroacetic acid are 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.

Similar content being viewed by others

Literature cited

  1. N. N. Suvorov, E. N. Sidorenko, L. Kh. Vinograd, N. M. Przhiyalgovskaya, T. N. Zykova, T. A. Guskova, T. N. Pershin, and M. V. Vasin, Khim. Geterotsikl. Soedin., Geterotsikl. Soedin., 1371 (1974).

  2. V. G. Avramenko, G. N. Pershin, P. I. Mushulov, O. O. Makeeva, V. Ya. Eryshev, L. B. Shagalov, and N. N. Suvorov, Khim-Farmats. Zh., No. 3, 15 (1970).

    Google Scholar 

  3. E. Johnson and D. G. Crosby, J. Org. Chem., 28, 1246 (1963).

    Google Scholar 

  4. H. Machemer, Angew. Chem., 64, 213 (1952).

    Google Scholar 

  5. E. F. Pratt and L. W. Botimer, J. Amer. Chem. Soc., 79, 5248 (1957).

    Google Scholar 

  6. H. E. Fritz, J. Org. Chem., 28, 1384 (1963).

    Google Scholar 

  7. W. von E. Döering, T. I. Taylor, and E. F. Schoenwaldt, J. Amer. Chem. Soc., 70, 455 (1948).

    Google Scholar 

  8. W. von E. Döering and T. C. Aschner, J. Amer. Chem. Soc., 75, 393 (1953).

    Google Scholar 

  9. C. Bottiger, Ber., 13, 1932 (1880).

    Google Scholar 

  10. S. W. Fox and M. Bullock, US Patent No. 2701250 (1955); Chem. Abstr., 50, P1922 (1956).

    Google Scholar 

  11. W. Salzer and H. Andersag, West German Patent No. 722809 (1939); Chem. Zentrallblat, 1, 567 (1943).

    Google Scholar 

  12. E. J. Stevens and S. W. Fox, J. Amer. Chem. Soc., 70, 2263 (1948).

    Google Scholar 

  13. M. Leekuing, Rec. Farm. Bioquim., 2, 45 (1964).

    Google Scholar 

  14. M. Clerk-Bory, Bull. Soc. Chim. France, 337 (1954).

  15. A. Jönsson, Acta Chem. Scand., 8, 119 (1954).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. D. I. Mendeleev Moscow Chemical-Engineering Institute, USSR

    V. G. Avramenko, V. D. Nazina, N. N. Levinova, D. N. Plutitskii & N. N. Suvorov

Authors
  1. V. G. Avramenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. D. Nazina
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. N. N. Levinova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. D. N. Plutitskii
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. N. N. Suvorov
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

See [1] for communication XCVIII.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1375–1378, October, 1974.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Avramenko, V.G., Nazina, V.D., Levinova, N.N. et al. Indole derivatives. Chem Heterocycl Compd 10, 1203–1206 (1974). https://doi.org/10.1007/BF00470163

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00470163

Keywords

Search

Navigation