Skip to main content
Log in

Chemistry of indole

XXXV. Synthesis of 2-amino-3-alkylindoles

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Under the influence of phosphorus oxychloride in an inert solvent, 1-aryl-2-acylhydrazines undergo intramolecular rearrangement to give 2-amino-3-alkylindoles. The latter are autooxidized in alkaline media to give 3-hydroxy-2-aminoindolenines or 3-hydroxy-2-iminoindolines. The structures of all of the compounds were proved by UV, IR, and PMR spectroscopy and also by mass-spectrometric data.

This is a preview of subscription content, log in via an institution to check access.

Access this article

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. L, G. Yudin, A. N. Kost, and E. Ya. Zinchenko, Khim. Geterotsikl. Soedin., 332 (1973).

  2. Yu. N. Portnov, G. A. Golubeva, and A. N. Kost, Khim. Geterotsikl. Soedin., 61 (1972).

  3. R. S. Sagitullin, V. I. Gorbunov, A. N. Kost, N.B. Kuplet-skaya, and V. V. Chistyakov, Khim. Geterotsikl. Soedin., 364 (1970).

  4. W. E. Stewart and T. H. Siddall, Chem. Rev., 70, 517 (1970).

    Google Scholar 

  5. A. N. Kost, G. A. Golubeva, and Yu. N. Portnov, Dokl. Akad. Nauk SSSR, 200, 342 (1970).

    Google Scholar 

  6. L. G. Yudin, V. A. Budylin, A. N. Kost, and V. I. Minkin, Dokl. Akad. Nauk SSSR, 176, 1096 (1967).

    Google Scholar 

  7. M. Nakagawa, H. Tamaguchi, and T. Hino, Tetrahedron Lett., 4035 (1970).

Download references

Author information

Authors and Affiliations

Authors

Additional information

See [1] for communication XXXIV.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 511–515, April, 1973.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Golubeva, G.A., Portnov, Y.N. & Kost, A.N. Chemistry of indole. Chem Heterocycl Compd 9, 471–475 (1973). https://doi.org/10.1007/BF00471528

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00471528

Keywords

Navigation