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Chemistry of Heterocyclic Compounds

, Volume 28, Issue 11, pp 1268–1273 | Cite as

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

  • V. I. Terenin
  • E. V. Kabanova
  • E. S. Feoktistova
  • V. V. Ovcharenko
  • Yu. G. Bundel
Article
  • 27 Downloads

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.

Keywords

Methyl Organic Chemistry Iodide General Process Process Scheme 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Plenum Publishing Corporation 1993

Authors and Affiliations

  • V. I. Terenin
    • 1
  • E. V. Kabanova
    • 1
  • E. S. Feoktistova
    • 1
  • V. V. Ovcharenko
    • 1
  • Yu. G. Bundel
    • 1
  1. 1.M. V. Lomonosov State UniversityMoscow

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