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Chemistry of Heterocyclic Compounds

, Volume 15, Issue 3, pp 296–301 | Cite as

Benzindoles

17. Vilsmeier reaction in the angular tetrahydrobenzindole series
  • L. B. Shagalov
  • G. M. Ostapchuk
  • A. D. Zlobina
  • V. N. Eraksina
  • T. A. Babushkina
  • A. M. Vasil'ev
  • N. N. Suvorov
Article
  • 137 Downloads

Abstract

The behavior of tetrahydro[4,5]- and tetrahydro[6,7]benzinodoles in the Vilsmeier reaction was investigated. It was established that the steric hindrance created by the cyclohexane ring condensed in the 4 and 5 positions has a substantial effect on the character of the reaction of tetrahydrobenzindoles with various N,N-disubstituted amines. A case of N-acylation in the investigated reactions is described. 3-Formyl-4,5,6,7-tetrahydro[4,5]- and 6,7,8,9-tetrahydro[6,7]-benzindoles were converted to the corresponding tryptamines.

Keywords

Organic Chemistry Cyclohexane Steric Hindrance Substantial Effect Tryptamine 
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

  • L. B. Shagalov
    • 1
    • 2
  • G. M. Ostapchuk
    • 1
    • 2
  • A. D. Zlobina
    • 1
    • 2
  • V. N. Eraksina
    • 1
    • 2
  • T. A. Babushkina
    • 1
    • 2
  • A. M. Vasil'ev
    • 1
    • 2
  • N. N. Suvorov
    • 1
    • 2
  1. 1.Institute of Biophysics of the Ministry of Public Health of the USSRMoscow
  2. 2.D. I. Mendeleev Moscow Institute of Chemical TechnologyMoscow

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