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

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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.

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REFERENCES

  1. I. S. Poddubnyi, Khim. Geterotsikl. Soedin., 774 (1995).

  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. D. N. Kozhevnikov, V. L. Rusinov, and O. N. Chupakhin, Adv. Heterocycl. Chem., 82, 261 (2002).

    Google Scholar 

  4. V. N. Kozhevnikov, A. M. Prokhorov, D. N. Kozhevnikov, V. L. Rusinov, and O. N. Chupakhin, Izv. Akad. Nauk, Ser. Khim., 1128 (2000).

  5. O. N. Chupakhin, V. L. Rusinov, E. N. Ulomsky, D. N. Kozhevnikov, and H. Neunhoeffer, Mendeleev Commun., 66 (1997).

  6. H. Neunhoeffer and V. Böhnisch, Liebigs Ann. Chem., 153 (1976).

  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. D. N. Kozhevnikov, E. N. Ulomsky, V. L. Rusinov, O. N. Chupakhin, and H. Neunhoeffer, Mendeleev Commun., 116 (1997).

  9. Yu. A. Azev, H. Neunhoeffer, S. Foro, H. J. Lindner, and S. V. Shorshnev, Mendeleev Commun., 229 (1995).

  10. Yu. A. Azev, O. V. Gryazeva, and S. V. Shorshnev, Khim. Geterotsikl. Soedin., 564 (2001).

  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. D. N. Kozhevnikov, I. S. Kovalev, V. L. Rusinov, and O. N. Chupakhin, Khim. Geterotsikl. Soedin., 1239 (2001).

  13. D. Doddi, G. Ercolani, and P. Mencarelli, J. Org. Chem., 57, 789 (1992).

    Google Scholar 

  14. T.-L. Ho, Tetrahedron, 41, 3 (1985).

    Google Scholar 

  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. H. Neunhoeffer, F. Weischedel and V. Böhnisch, Liebigs Ann. Chem., 750, 12 (1971).

    Google Scholar 

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Authors
  1. D. N. Kozhevnikov
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  2. A. M. Prokhorov
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  3. V. L. Rusinov
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  4. O. N. Chupakhin
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Kozhevnikov, D.N., Prokhorov, A.M., Rusinov, V.L. et al. Regioselectivity of Nucleophilic Attack on the Reactions of 1,2,4-Triazine 4-Oxides with Certain C-Nucleophiles. Chemistry of Heterocyclic Compounds 40, 911–915 (2004). https://doi.org/10.1023/B:COHC.0000044574.23114.58

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  • DOI: https://doi.org/10.1023/B:COHC.0000044574.23114.58

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