Chemistry of Heterocyclic Compounds

, Volume 29, Issue 3, pp 307–312 | Cite as

The vicarious intramolecular substitution reactions. I. Synthesis of condensed indolizines based on 2-quinoxalylacetonitriles

  • S. V. Litvinenko
  • Yu. M. Volovenko
  • F. S. Babichev
Article

Abstract

The interaction of α-substituted 2-(3-chloro)quinoxalylacetonitriles with azines to give condensed indolizino [2,3-b]quinoxalines has been studied. A mechanism for the reaction has been proposed which includes an intramolecular vicarious substitution of hydrogen in the azolium salt nucleus. The limits of utility of the reaction have been determined and some chemical properties of the compounds synthesized have been studied.

Keywords

Hydrogen Organic Chemistry Chemical Property Azolium Substitution Reaction 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    M. Makosha. Usp. Khim., 58, No. 8, 1298 (1989).Google Scholar
  2. 2.
    M. Makosha (Makosza). Acc. Chem. Res., 20(8), 282 (1987).Google Scholar
  3. 3.
    Yu. M. Volovenko, S. V. Litvinenko, and F. S. Babichev. Dokl. Akad. Nauk Ukr. SSR, Ser. B, No. 4, 37 (1988).Google Scholar
  4. 4.
    Yu. M. Volovenko, S. V. Litvinenko, V. I. Savich, and F. S. Babichev. Dokl. Akad. Nauk Ukr. SSR, Ser. B, No. 1, 96 (1992).Google Scholar
  5. 5.
    E. R. Pratt and J. C. Keresztesi, J. Org. Chem., 32, No. 1, 9 (1967).Google Scholar
  6. 6.
    R. Shriner, R. Fuson, and T. Morrel, Identification of Organic Compounds [Russian translation], Mir, Moscow (1983).Google Scholar
  7. 7.
    P. Sammes (ed.), General Organic Chemistry [Russian translation], Vol. 8, Khimiya, Moscow (1985).Google Scholar
  8. 8.
    E. V. Ganke and B. Zwaneburg. Synthesis, 8, 519 (1975).Google Scholar
  9. 9.
    R. B. Fox and D. L. Venezky. J. Amer. Chem. Soc., 78, No. 7–8, 1662 (1956).Google Scholar

Copyright information

© Plenum Publishing Corporation 1993

Authors and Affiliations

  • S. V. Litvinenko
    • 1
  • Yu. M. Volovenko
    • 1
  • F. S. Babichev
    • 1
  1. 1.Kiev Technological Institute for the Food IndustryKiev

Personalised recommendations