Skip to main content
SpringerLink
Log in

Indole derivatives. 135. 5-[2-(4-Methoxyphenyl)ethenyl]indolines and indoles

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

5-[2-(4-Methoxyphenyl)ethenyl]indolines were obtained from 5-formyl-1-methyl- or 5-forrayl-1-benzylindolines by the Witting reaction with 4-methoxybenzylidenetriphenylphosphorane. Their dehydrogenation led to the formation of the corresponding compounds of the indole series. The corresponding hydroxy compounds were obtained by demethylation of the methoxyindole with boron tribromide and were converted into the acetoxy derivatives of indoline and indole.

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. R. N. Akhvlediani, M. M. Khachidze, V. N. Eraksina, and N. N. Suvorov, Khim. Geterotsikl., No. 11, 1476 (1988).

    Google Scholar 

  2. L. N. Chupina, V. F. Shner, G. I. Gritsina, A. I. Terekhina, and N. N. Suvorov, Khim. Geterotsikl. Soedin., No. 4, 466 (1984).

    Google Scholar 

  3. W. Chaikin and W. V. Brown, J. Am. Chem. Soc., 71, 122 (1949).

    Google Scholar 

  4. J. Lee, A. Leiring, L. Berger, and S. D. Heinman, Jubilee Vol. Emil. Barrell, (1946) p. 264.

  5. J. F. Eastman and D. I. Cannon, J. Org. Chem., 25, 1504 (1960).

    Google Scholar 

  6. A. W. Jonson and V. L. Kyllingstad, J. Org. Chem., 31, 334 (1966).

    Google Scholar 

  7. G. Wittig and U. Schollkopf, Chem. Ber., 87, 1318 (1954).

    Google Scholar 

  8. K. B. Becker, Synthesis, No. 5, 341 (1983).

    Google Scholar 

  9. G. Markl and A. Merz, Synthesis, No. 5, 295 (1973).

    Google Scholar 

  10. J. Attenburrow, A. F. Cameron, J. H. Chapman, K. H. Evans, B. A. Huns, A. B. Jansen, and T. Walker, J. Chem. Soc., No. 3, 1094 (1952).

    Google Scholar 

  11. P. N. Craig, F. P. Nabenhaver, P. M. Williams, E. Masko, and J. Tower, J. Am. Chem. Soc., 74, 1316 (1952).

    Google Scholar 

  12. G. A. Olah, S. C. Narang, G. B. Gupta, and R. Malnotra, J. Org. Chem., 44, 1247 (1979).

    Google Scholar 

  13. J. I. N. McOmie, M. L. Walts, and D. E. West, Tetrahedron, 24, 2289 (1968).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. S. Ordzhonikidze All-Union Scientific-Research Pharmaceutical Chemistry Institute, Moscow

    L. N. Chupina, V. F. Shner & N. N. Suvorov

Authors
  1. L. N. Chupina
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. F. Shner
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. N. N. Suvorov
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

For communication 134, see [1].

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 911–914, July, 1989.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Chupina, L.N., Shner, V.F. & Suvorov, N.N. Indole derivatives. 135. 5-[2-(4-Methoxyphenyl)ethenyl]indolines and indoles. Chem Heterocycl Compd 25, 758–761 (1989). https://doi.org/10.1007/BF00472745

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00472745

Keywords

Search

Navigation