Chemistry of Heterocyclic Compounds

, Volume 40, Issue 7, pp 895–902 | Cite as

Oxidative Addition of N-Aminophthalimide and 3-Amino-2-methylquinazolin-4(3H)-one to Conjugated Azocyclopentenes and Azocyclohexenes

  • S. M. Buchaka
  • M. A. Kuznetsov
  • J. G. Schantl


The oxidation of N-aminophthalimide and 3-amino-2-methylquinazolin-4(3H)-one in the presence of conjugated azocyclopentenes, azocyclohexenes, and 3-arylazocyclohexen-2-ones gives adducts at the carbon-carbon double bond corresponding to C-azoaziridines and/or bicyclic 2H-1,2,3-triazoles.

C-azoaziridines 1-azocycloalkenes 3-azocycloalken-2-ones 3-amino-2-methylquinazolin-4(3H)-one N-aminophthalimide 2H-1,2,3-triazoles oxidative aminoaziridination 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    M. A. Kuznetsov and B. V. Ioffe, Usp. Khim., 58, 1271 (1989).Google Scholar
  2. 2.
    A. A. Suvorov and M. A. Kuznetsov, Usp. Khim., 56, 1324 (1987).Google Scholar
  3. 3.
    M. A. Kuznetsov, V. N. Belov, and S. M. Buchaka, Zh, Org. Khim,in press.Google Scholar
  4. 4.
    M. A. Kuznetsov, L. M. Kuznetsova, and J. G. Schantl, Zh. Org. Khim., 36, 836 (2000).Google Scholar
  5. 5.
    M. A. Kuznetsov, L. M. Kuznetsova, J. G. Schantl, and K. Wurst, Eur. J. Org. Chem., 1309 (2001).Google Scholar
  6. 6.
    L. Hoesch and A. S. Dreiding, Helv. Chim. Acta, 58, 980 (1975).Google Scholar
  7. 7.
    R. S. Atkinson, Tetrahedron, 55, 1519 (1999).Google Scholar
  8. 8.
    R. S. Atkinson and J. R. Malpass, J. Chem. Soc., Perkin Trans. 1, 2242 (1977).Google Scholar
  9. 9.
    H.-O. Kalinowski, S. Berger, and S. Braun, 13 C NMR Spectroscopy, Georg Thieme Verlag, Stuttgart (1984).Google Scholar
  10. 10.
    J. G. Schantl and P. Hebeisen, Tetrahedron, 46, 395 (1990).Google Scholar
  11. 11.
    J. Schantl, Monatsh. Chem., 103, 1705, 1718 (1972).Google Scholar
  12. 12.
    J. Schantl, Monatsh. Chem., 105, 220 (1974).Google Scholar
  13. 13.
    S. Brodka and H. Simon, Chem. Ber., 102, 3647 (1969).Google Scholar
  14. 14.
    B. T. Gillis and M. P. La Montagne, J. Org. Chem., 33, 762 (1968).Google Scholar
  15. 15.
    H. J. Teuber, E. Worbs, and D. Cornelius, Chem. Ber., 101, 3918 (1968).Google Scholar
  16. 16.
    H. D. K. Drew and H. H. Hatt, J. Chem. Soc., 16 (1937).Google Scholar
  17. 17.
    D. J. Anderson, T. L. Gilchrist, D. C. Horwell, and C. W. Rees, J. Chem. Soc. (C), 576 (1970).Google Scholar

Copyright information

© Plenum Publishing Corporation 2004

Authors and Affiliations

  • S. M. Buchaka
  • M. A. Kuznetsov
  • J. G. Schantl

There are no affiliations available

Personalised recommendations