Advertisement

Chemistry of Heterocyclic Compounds

, Volume 40, Issue 7, pp 911–915 | Cite as

Regioselectivity of Nucleophilic Attack on the Reactions of 1,2,4-Triazine 4-Oxides with Certain C-Nucleophiles

  • D. N. Kozhevnikov
  • A. M. Prokhorov
  • V. L. Rusinov
  • O. N. Chupakhin
Article

Abstract

The addition of CH-active compounds to 6-aryl-1,2,4-triazine 4-oxide is reversible and occurs under conditions of kinetic control at position 5 of the heterocycle to form cyclic C(5)-σH adducts. Under conditions of thermodynamic control the nucleophilic attack is directed to position 3 of the heterocycle and is accompanied by its opening to form the more stable open chain addition products. Attack of ethylmagnesium bromide is directed exclusively to the 5 position of the 6-aryl-1,2,4-triazine 4-oxides as a result of the irreversibility of the given reaction.

1,3-diketones organomagnesium compounds 1,2,4-triazine nucleophilic substitution of hydrogen 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

REFERENCES

  1. 1.
    I. S. Poddubnyi, Khim. Geterotsikl. Soedin., 774 (1995).Google Scholar
  2. 2.
    O. N. Chupakhin, V.N. Charushin, and H. C. van der Plas, Nucleophilic Aromatic Substitution of Hydrogen, Academic Press, New York, San Diego (1994), p. 367.Google Scholar
  3. 3.
    D. N. Kozhevnikov, V. L. Rusinov, and O. N. Chupakhin, Adv. Heterocycl. Chem., 82, 261 (2002).Google Scholar
  4. 4.
    V. N. Kozhevnikov, A. M. Prokhorov, D. N. Kozhevnikov, V. L. Rusinov, and O. N. Chupakhin, Izv. Akad. Nauk, Ser. Khim., 1128 (2000).Google Scholar
  5. 5.
    O. N. Chupakhin, V. L. Rusinov, E. N. Ulomsky, D. N. Kozhevnikov, and H. Neunhoeffer, Mendeleev Commun., 66 (1997).Google Scholar
  6. 6.
    H. Neunhoeffer and V. Böhnisch, Liebigs Ann. Chem., 153 (1976).Google Scholar
  7. 7.
    V. L. Rusinov, D. N. Kozhevnikov, E. N. Ulomsky, O. N. Chupakhin, G. G. Aleksandrov, and H. Neunhoeffer, Zh. Org. Khim., 34, 429 (1998).Google Scholar
  8. 8.
    D. N. Kozhevnikov, E. N. Ulomsky, V. L. Rusinov, O. N. Chupakhin, and H. Neunhoeffer, Mendeleev Commun., 116 (1997).Google Scholar
  9. 9.
    Yu. A. Azev, H. Neunhoeffer, S. Foro, H. J. Lindner, and S. V. Shorshnev, Mendeleev Commun., 229 (1995).Google Scholar
  10. 10.
    Yu. A. Azev, O. V. Gryazeva, and S. V. Shorshnev, Khim. Geterotsikl. Soedin., 564 (2001).Google Scholar
  11. 11.
    A. Rykowski, O. N. Chupakhin, D. N. Kozhevnikov, V. N. Kozhevnikov, V. L. Rusinov, and H. C. van der Plas, Heterocycles, 55, 127 (2001).Google Scholar
  12. 12.
    D. N. Kozhevnikov, I. S. Kovalev, V. L. Rusinov, and O. N. Chupakhin, Khim. Geterotsikl. Soedin., 1239 (2001).Google Scholar
  13. 13.
    D. Doddi, G. Ercolani, and P. Mencarelli, J. Org. Chem., 57, 789 (1992).Google Scholar
  14. 14.
    T.-L. Ho, Tetrahedron, 41, 3 (1985).Google Scholar
  15. 15.
    D. N. Kozhevnikov, V. N. Kozhevnikov, V. L. Rusinov, O. N. Chupakhin, E. O. Sidorov, and N. A. Klyuev, Zh. Org. Khim., 34, 423 (1998).Google Scholar
  16. 16.
    H. Neunhoeffer, F. Weischedel and V. Böhnisch, Liebigs Ann. Chem., 750, 12 (1971).Google Scholar

Copyright information

© Plenum Publishing Corporation 2004

Authors and Affiliations

  • D. N. Kozhevnikov
  • A. M. Prokhorov
  • V. L. Rusinov
  • O. N. Chupakhin

There are no affiliations available

Personalised recommendations