Chemistry of Heterocyclic Compounds

, Volume 18, Issue 10, pp 1098–1103 | Cite as

Cyclization of N-alkylazinium cations with bisnucleophiles. 6. Cycloelimination of tetrahydro-endo-furo[2,3-b]quinoxalines leading to 2,3-disubstituted tetrahydroquinoxalines

  • M. G. Ponizovskii
  • O. N. Chupakhin
  • V. N. Charushin
  • G. G. Aleksandrov


The reaction of an N-methylquinoxalinium salt with a β-diketone under thermodynamic-control conditions leads to 2,3-disubstituted tetrahydroquinoxaline via cycloelimination of the initially formed tetrahydro-endo-furo[2,3-b]quinoxaline.


Organic Chemistry Quinoxaline Tetrahydroquinoxaline 
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Literature cited

  1. 1.
    O. N. Chupakhin, V. N. Charushin, L. M. Naumova, A. I. Rezvukhin, and N. A. Klyuev, Khim. Geterotsikl. Soedin., No. 11, 1549 (1981).Google Scholar
  2. 2.
    T. Kauffmann, Angew. Chem., Int. Ed., 13, 627 (1974).Google Scholar
  3. 3.
    O. N. Chupakhin, V. N. Charushin, L. M. Naumova, and A. I. Rezvukhin, Dokl. Akad. Nauk SSSR, No. 2, 384 (1982).Google Scholar
  4. 4.
    V. N. Churashin, O. N. Chupakhin, and A. I. Rezvukhin, Heterocycles, 16, 195 (1981).Google Scholar
  5. 5.
    R. Aquilera, J.-C. Duplan, and C. Nofre, Bull. Soc. Chim. Fr., 4491 (1968).Google Scholar
  6. 6.
    L. E. Sutton (editor), Tables of Interatomic Distances and Configurations in Molecules and Ions, Supplement 1956–1959, London (1965).Google Scholar
  7. 7.
    W. A. Mosher and W. E. Meier, J. Org. Chem., 35, 2934 (1970).Google Scholar
  8. 8.
    C. Cavagnol and F. Y. Wiselogie, J. Am. Chem. Soc., 48, 795 (1947).Google Scholar
  9. 9.
    W. Cruba and H. Poradovska, Roczn. Chem., 48, 1237 (1974).Google Scholar
  10. 10.
    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 1983

Authors and Affiliations

  • M. G. Ponizovskii
    • 1
  • O. N. Chupakhin
    • 1
  • V. N. Charushin
    • 1
  • G. G. Aleksandrov
    • 1
  1. 1.S. M. Kirov Ural Polytechnic InstituteSverdlovsk

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