Advertisement

Chemistry of Heterocyclic Compounds

, Volume 17, Issue 2, pp 189–194 | Cite as

Reactions of N-alkylazinium cations. 2. Reaction of quinoxalinium salts with malonodinitrile and cyanoacetic ester

  • V. N. Charushin
  • O. N. Chupakhin
  • G. M. Petrova
  • E. O. Sidorov
  • N. A. Klyuev
  • L. G. Egorova
Article

Abstract

N-Alkylquinoxalinlum salts react with malonodinitrile and cyanoacetic ester carbanions to give addition products, which, due to favorably disposed CN groups and active CH centers, subsequently undergo intramolecular cyclization with the formation of a five-membered ring.

Keywords

Ester Organic Chemistry Addition Product Quinoxalinium Intramolecular Cyclization 
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.
    O. N. Chupakhin, V. N. Charushin, and E. O. Sidorov, Khim. Geterotsikl. Soedin., No. 5, 666 (1979).Google Scholar
  2. 2.
    J. Joule and G. Smit, Fundamentals of the Chemistry of Heterocyclic Compounds [Russian translation], Mir, Moscow (1975).Google Scholar
  3. 3.
    J. W. Bunting and M. G. Meathrel, Can. J. Chem., 50, 919 (1972).Google Scholar
  4. 4.
    J. A. Zoltevicz, T. M. Oestreich, J. K. O'Halloran, and L. S. Helmick, J. Org. Chem., 38, 1949 (1973).Google Scholar
  5. 5.
    A. K. Sheinkman, Kh. Ya. Lopatinskaya, N. A. Klyuev, and Zh. K. Torosyan, Khim. Geterotsikl. Soedin., No. 2, 234 (1980).Google Scholar
  6. 6.
    V. N. Charushin, I. Ya. Postovskii, and O. N. Chupakhin, Dokl. Akad. Nauk SSSR, 246, 351 (1979).Google Scholar
  7. 7.
    H. Takayama and T. Okamoto, Chem. Pharm. Bull., 26, 2435 (1978).Google Scholar
  8. 8.
    The Sadtler Standard Spectra. C-13 NMR Spectra, Vol. 22, No. 4240c, Sadtler Research Laboratories, Philadelphia (1978).Google Scholar
  9. 9.
    Yu. A. Sharanin and V. K. Promonenkov, Izv. Sibirsk. Otd. Akad. Nauk SSSR, No. 2, 80 (1980).Google Scholar
  10. 10.
    E. N. Zil'berman, in: Reactions of Nitriles [in Russian], Khimiya, Moscow (1972), p. 142.Google Scholar
  11. 11.
    H. Böhme and H. C. Viehe, Iminium Salts in Organic Chemistry. Part II, Intersci. Publ. (1979), p. 552.Google Scholar
  12. 12.
    I. Ya. Bershtein and Yu. L. Kaminskii, Spectrophotometric Analysis in Organic Chemistry [in Russian], Khimiya, Leningrad (1975), p. 39.Google Scholar

Copyright information

© Plenum Publishing Corporation 1981

Authors and Affiliations

  • V. N. Charushin
    • 1
  • O. N. Chupakhin
    • 1
  • G. M. Petrova
    • 1
  • E. O. Sidorov
    • 1
  • N. A. Klyuev
    • 1
  • L. G. Egorova
    • 1
  1. 1.S. M. Kirov Ural Polytechnic InstituteSverdlovsk

Personalised recommendations