Skip to main content
SpringerLink
Log in

Reamination in the recyclization of pyrrolo-[1,2-a]pyrazine salts into 6- and 8-aminoindolizines. General process scheme

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Rearrangement of the methyl iodides of 1- and 3-alkyl-substituted pyrrolo[1,2-a]pyrazines in the presence of various alkylamines afforded a mixture of 8- and 6-aminoindolizines, respectively, with and without exchange of the methylamine fragment. The ratio of the products of direct and exchange recyclization was dictated by the size of the N-alkyl substituents in the reagent and starting salt. Rearrangement of the 1-alkylpyrrolo[1,2-a]pyrazinium salts proceeded via the breaking of the C(3) -N(2) bond, and rearrangement of the 3-alkylpyrrolo-[1,2-a]pyrazinium salts via the breaking of the C(1) -N(2) bond.

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

References

  1. V. I. Terenin, E. V. Kabanova, E. S. Feoktistova, and Y. G. Bundel', Khim. Geterotsikl. Soedin., No. 3, 424 (1989).

    Google Scholar 

  2. V. I. Terenin, E. V. Kabanova, and Yu. G. Bundel', Khim. Geterotsikl. Soedin., No. 6, 763 (1991).

    Google Scholar 

  3. R. S. Sagitullin, S. P. Gromov, and A. N. Kost, Dokl. Akad. Nauk, 236, 634 (1977).

    Google Scholar 

  4. Ya. F. Freimanis, Chemistry of Enaminoketones, Enaminoimines and Enaminothiones [in Russian], Zinatne, Riga (1974), p. 211.

    Google Scholar 

  5. V. Galasso, G. De Alti, and A. Bigotto, Theor. Chim. Acta, No. 9, 222 (1967).

    Google Scholar 

  6. W. W. Paudler, C. I. Patsy Chao, and L. S. Helmick, J. Heterocycl. Chem., 9, 1157 (1972).

    Google Scholar 

  7. A. N. Kost, D. V. Yashunskii, S. P. Gromov, and R. S. Sagitullin, Khim. Geterotsikl. Soedin., No. 9, 1268 (1980).

    Google Scholar 

  8. V. I. Terenin, E. V. Kabanova, E. S. Feoktistova, and Yu. G. Bundel', Khim. Geterotsikl. Soedin., No. 7, 928 (1992).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. M. V. Lomonosov State University, Moscow

    V. I. Terenin, E. V. Kabanova, E. S. Feoktistova, V. V. Ovcharenko & Yu. G. Bundel

Authors
  1. V. I. Terenin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. E. V. Kabanova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. E. S. Feoktistova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. V. V. Ovcharenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Yu. G. Bundel
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated from Khimiya Geterotsiklicheskikikh Soedinenii, No. 11, pp. 1485–1490, November, 1992.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Terenin, V.I., Kabanova, E.V., Feoktistova, E.S. et al. Reamination in the recyclization of pyrrolo-[1,2-a]pyrazine salts into 6- and 8-aminoindolizines. General process scheme. Chem Heterocycl Compd 28, 1268–1273 (1992). https://doi.org/10.1007/BF00532075

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00532075

Keywords

Search

Navigation