Advertisement

Chemistry of Heterocyclic Compounds

, Volume 19, Issue 8, pp 871–876 | Cite as

Pyrroloindoles. 8. Electrophilic substitution in the 1H,5H-pyrrolo[2,3-f]indole and 3H,6H-pyrrolo[3,2-e]indole series

  • D. O. Kadzhrishvili
  • Sh. A. Samsoniya
  • E. N. Gordeev
  • L. N. Kurkovskaya
  • V. E. Zhigachev
  • N. N. Suvorov
Article

Abstract

The principles of the electron density distribution in 1H,5H-pyrrolo [2,3-f]indole and 3H,6H-pyrrolo[3,2-e]indole molecules were determined on the basis of quantumchemical calculations. These results were confirmed by the results of the investigated electrophilic-substitution reactions. The reaction centers of these compounds proved to be the same positions as in indole, viz., the 3 and 7 and 1 and 8 positions, respectively. The impossibility of 1,8-disubstitution in the angular heteroring was demonstrated in the case of bulky substituents; this was explained by a steric effect.

Keywords

Organic Chemistry Reaction Center Indole Density Distribution Steric Effect 
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.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    S. V. Dolidze, Sh. A. Samsoniya, and N. N. Suvorov, Khim. Geterotsikl. Soedin., No. 5, 608 (1983).Google Scholar
  2. 2.
    V. G. Maslov, Zh. Strukt. Khim., 18, 414 (1977).Google Scholar
  3. 3.
    O. A. Yuzhakova, L. N. Kurkovskaya, N. N. Shapet'ko, V. K. Potapov, and A. I. Shatenshtein, Teor. Éksp. Khim., 7, 962 (1971).Google Scholar
  4. 4.
    Organic Syntheses [Russian translation], Collective Vol. 11, Inostr. Lit., Moscow (1949), p. 30.Google Scholar
  5. 5.
    G. Kinast and L. F. Tietze, Angew. Chem., 88, 261 (1976).Google Scholar
  6. 6.
    J. E. Saxton, J. Chem. Soc., No. 9, 3592 (1952).Google Scholar
  7. 7.
    V. G. Avramenko, V. D. Nazina, and N. N. Suvorov, Khim. Geterotsikl. Soedin., No. 8, 1071 (1970).Google Scholar

Copyright information

© Plenum Publishing Corporation 1984

Authors and Affiliations

  • D. O. Kadzhrishvili
    • 1
    • 2
  • Sh. A. Samsoniya
    • 1
    • 2
  • E. N. Gordeev
    • 1
    • 2
  • L. N. Kurkovskaya
    • 1
    • 2
  • V. E. Zhigachev
    • 1
    • 2
  • N. N. Suvorov
    • 1
    • 2
  1. 1.Tbilisi State UniversityTbilisi
  2. 2.D. I. Mendeleev Moscow Institute of Chemical TechnologyMoscow

Personalised recommendations