REGIOSELECTIVITY OF NUCLEOPHILIC ATTACK IN THE REACTIONS OF 1,2,4-TRIAZINE 4-OXIDES WITH CERTAIN C-NUCLEOPHILES

Authors

  • D. N. Kozhevnikov Ural State Technical University, Yekaterinburg 620002
  • A. M. Prokhorov Ural State Technical University, Yekaterinburg 620002
  • V. L. Rusinov Ural State Technical University, Yekaterinburg 620002
  • O. N. Chupakhin iI. Ya. Postovsky Institute of Organic Synthesis, Ural Section, Russian Academy of Sciences, Yekaterinburg 620219

Keywords:

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

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.

How to Cite
Kozhevnikov, D. N.; Prokhorov, A. M.; Rusinov, V. L.; Chupakhin, O. N. Chem. Heterocycl. Compd. 2004, 40, 911. [Khim. Geterotsikl. Soedin. 2004, 1060.]

For this article in the English edition, see DOI https://doi.org/10.1023/B:COHC.0000044574.23114.58

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Published

2004-07-25

Issue

No. 7 (2004)

Section

Original Papers