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


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.


Nitrogen Organic Chemistry Ketone Nitrogen Atom Indole 
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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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