Skip to main content
SpringerLink
Log in

Indoles

L. m-Monosubstituted diarylhydrazines in the Fischer indole synthesis (reaction mechanism)

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The cyclization of cyclohexanone m-monosubstituted α,α-diphenylhydrazones under the conditions of the Fischer reaction was studied. It is shown that in the case of both donor (R = OCH3) and acceptor (R = Cl) substituents all three possible isomeric tetrahydrocarbazoles are formed as a result of the reaction. These data constituted an unambiguous confirmation of the concept of the occurrence of the principal step in the Fischer reaction (the step involving the formation of a carbon-carbon bond) via a sigmatropic [3,3]-rearrangement mechanism. The ratios of the tetrahydrocarbazoles in the reaction mixtures under various cyclization conditions were determined independently by PMR, IR, and mass spectrometry and gas-liquid chromatography. The structures of the products were proved by the set of spectral characteristics and by alternative synthesis.

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. N. M. Przheval'skii, I. I. Grandberg, and N. A. Klyuev, Khim. Geterotsikl. Soedin., No. 8, 1065 (1976).

    Google Scholar 

  2. I. I. Grandberg, Izv. Timiryazev, Sel'skokhoz. Khim. Akad., No. 5, 188 (1972).

    Google Scholar 

  3. I. Gruda and J. Braitburg, Polish Patent No. 54428 (Cl. C07c), Jan. 20 (1968); Chem. Abstr., 70, 11329k (1969).

    Google Scholar 

  4. F. Ullmann, Ann., 355, 338 (1901).

    Google Scholar 

  5. R. O. Matevosyan, I. Ya. Postovskii, and A. K. Chirkov, Zh. Obshch. Khim., 29, 858 (1959).

    Google Scholar 

  6. R. H. Poirier and F. Benington, J. Am. Chem. Soc., 74, 3192 (1952).

    Google Scholar 

  7. R. Iyer, A. Jackson, P. V. R. Shannon, andNaidoo Balakrishna, J. Chem. Soc., Perkin Trans., Part II, No. 6, 872 (1973).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. K. A. Timiryazev Moscow Agricultural Academy, 125008, Moscow

    N. M. Przheval'skii, I. I. Grandberg, N. A. Klyuev & A. B. Belikov

Authors
  1. N. M. Przheval'skii
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. I. I. Grandberg
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. N. A. Klyuev
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. B. Belikov
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

See [1] for communication XLIX.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1349–1355, October, 1978.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Przheval'skii, N.M., Grandberg, I.I., Klyuev, N.A. et al. Indoles. Chem Heterocycl Compd 14, 1093–1099 (1978). https://doi.org/10.1007/BF00469948

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00469948

Keywords

Search

Navigation