Advertisement

Chemistry of Heterocyclic Compounds

, Volume 26, Issue 5, pp 565–572 | Cite as

Cyclizations of N-alkyl-substituted azinium cations with bifunctional nucleophiles. 28. Orientation of the nucleophile in the reaction of quinoxalinium salts with indan-1,3-dione

  • G. M. Petrova
  • M. G. Ponizovskii
  • V. N. Charushin
  • G. G. Aleksandrov
  • E. O. Sidorov
  • O. N. Chupakhin
Article
  • 38 Downloads

Abstract

In reactions with quinoxalinium salts in alcoholic-base media indan-1,3-dione acts as a C nucleophile, adding at the 2 or 3 position of the heterocycle to give the corresponding ylidene derivatives; attack by the nucleophile at the C(3) atom (the Β position relative to the quaternary nitrogen atom) is preceded by addition of alcohol at the a position. Dissociative substitution at the C(2) atom in 2-alkoxy-3-(1,3-dioxoindan-2-ylidene)-1,2,3,4-tetrahydroquinoxalines by another nucleophile makes it possible to regard lyate complexes as probable intermediates in cyclizations of 1,4-diazinium salts with dinucleophiles.

Keywords

Nitrogen Alcohol Organic Chemistry Nitrogen Atom Dione 
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. G. Alekseev, V. N. Charushin, O. N. Chapakhin, G. G. Aleksandrov, A. I. Chernyshev, and S. V. Shorshnev, Izv. Akad. Nauk SSSR, No. 7, 1637 (1989).Google Scholar
  2. 2.
    V. N. Charushin, O. N. Chupakhin, and H. C. van der Plas, Adv. Heterocycl. Chem. 43, 301 (1988).Google Scholar
  3. 3.
    O. N. Chupakhin, V. N. Charushin, and A. I. Chernyshev, Prog. NMR Spectrosc. 20, No. 2, 95 (1988).Google Scholar
  4. 4.
    M. G. Ponizovskii, O. N. Chupakhin, V. N. Charushin, and G. G. Aleksandrov, Khim. Geterotsikl. Soedin., No. 10, 1410 (1982).Google Scholar
  5. 5.
    L. E. Satton (ed.), Tables of Interatomic Distances and Configurations in Molecules and Ions: Supplement, London (1965), p. 1956.Google Scholar
  6. 6.
    V. N. Charushin, M. G. Ponizovskii, O. N. Chupakhin, E. O. Sidorov, and I. M. Sosonkin, Khim. Geterotsikl. Soedin., No. 5, 669 (1985).Google Scholar
  7. 7.
    J. Amiel, J. Ploguin, L. Sparfel, J. le Bant, and R, Floch, Compt. Rend. Ser. C 279, 747 (1974).Google Scholar
  8. 8.
    F. Terrier, Chem. Rev. 82, 77 (1982).Google Scholar
  9. 9.
    G. A. Artamkina, N. P. Egorov, and I. P. Beletskaya, Chem. Rev. 82, 427 (1982).Google Scholar
  10. 10.
    I. M. Sosonkin, G. L. Kalb, I. V. Kazantseva, M. G. Ponizovskii, V. N. Charushin, and O. N. Chupakhin, Khim. Geterotsikl. Soedin., No. 8, 1110 (1987).Google Scholar
  11. 11.
    E. Buncel and J. G. K. Webb, Tetrahedron Lett. 49, 4417 (1976).Google Scholar
  12. 12.
    V. N. Charushin, M. G. Ponizovskii, O. N. Chupakhin, A. I. Rezvukhin, G. M. Petrova, and Yu. A. Efremov, Khim. Geterotsikl. Soedin., No 11, 1543 (1981).Google Scholar

Copyright information

© Plenum Publishing Corporation 1990

Authors and Affiliations

  • G. M. Petrova
    • 1
  • M. G. Ponizovskii
    • 1
  • V. N. Charushin
    • 1
  • G. G. Aleksandrov
    • 1
  • E. O. Sidorov
    • 1
  • O. N. Chupakhin
    • 1
  1. 1.S. M. Kirov Ural Polytechnical InstituteSverdlovsk

Personalised recommendations