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Chemistry of Heterocyclic Compounds

, Volume 14, Issue 7, pp 745–751 | Cite as

Effect of protection of amino group on direction of reaction of 2-aminoindole with α,β-unsaturated ketones

  • R. S. Sagitullin
  • T. Yagodzin'ski
  • A. N. Kost
  • V. V. Men'shikov
Article
  • 56 Downloads

Abstract

The electron-acceptor properties of arylsulfonyl and carbobenzoxy groups decrease the probability of primary electrophilic attack at the nitrogen atom. They also determine primary attack at the 3-C atom of the indole ring. Michael addition products, 3,4-dihydro-α-carbolines, and α-carbolines themselves are obtained, depending on the reaction conditions. The reaction with α,β-unsaturated ketones proceeds under milder conditions in the case of 2-benzyloxycarbonylaminoindole.

Keywords

Nitrogen Organic Chemistry Ketone Nitrogen Atom Indole 
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 1979

Authors and Affiliations

  • R. S. Sagitullin
    • 1
  • T. Yagodzin'ski
    • 1
  • A. N. Kost
    • 1
  • V. V. Men'shikov
    • 1
  1. 1.M. V. Lomonosov Moscow State UniversityMoscow

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