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Chemistry of Heterocyclic Compounds

, Volume 7, Issue 11, pp 1401–1405 | Cite as

Indole chemistry

XXI. Nitration of 3-acylindoles
  • L. G. Yudin
  • A. I. Pavlyuchenko
  • V. A. Budylin
  • V. I. Minkin
  • A. N. Kost
Article

Abstract

In the nitration of 3-acyl- and 3-carbethoxyindoles with various nitrating agents, the ratio of substitution of the hydrogen atoms in the 4 or 6 positions or the replacement of the acyl group in the 3 position by a nitro group depend on the conditions. Replacement of the carbethoxy group in the 3 position is not observed. The experimental data were compared with the reactivity indexes calculated by the LCAO MO method. It was concluded that replacement of the hydrogen atoms in the benzene ring of the investigated models proceeds as electrophilic attack of an unprotonated molecule of the indole compound.

Keywords

Nitrate Benzene Organic Chemistry Hydrogen 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

© Consultants Bureau 1974

Authors and Affiliations

  • L. G. Yudin
    • 1
    • 2
  • A. I. Pavlyuchenko
    • 1
    • 2
  • V. A. Budylin
    • 1
    • 2
  • V. I. Minkin
    • 1
    • 2
  • A. N. Kost
    • 1
    • 2
  1. 1.M. V. Lomonosov Moscow State UniversityUSSR
  2. 2.Rostov State UniversityRostov-on-Don

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