REACTIONS OF 1,2,4-TRIAZINES WITH NUCLEOPHILES. 6. USE OF S<sub>N</sub><sup>H</sup> METHODOLOGY FOR THE DIRECT INTRODUCTION OF CYCLIC DIKETONE RESIDUE INTO THE 1,2,4-TRIAZINE RING

Authors

  • Д. Н. Кожевников Ural State University, Ekaterinburg 620002
  • И. С. Ковалев Ural State University, Ekaterinburg 620002
  • В. Л. Русинов Ural State University, Ekaterinburg 620002
  • О. Н. Чупахин Ural State University, Ekaterinburg 620002

Keywords:

1,2,4-triazines, nucleophilic substitution of hydrogen, cyclic β-diketones

Abstract

3-R-6-Phenyl-1,2,4-triazine 4-oxides react with cyclic β-diketones (dimethylbarbituric acid, dimedone, and indan) in both acidic (substrate activation) and basic conditions (nucleophile activation) with formation of σH-adducts, intermediates in the nucleophilic substitution of hydrogen (SNH) in 3-R-5-Nu-4-hydroxy-6-phenyl-4,5-dihydro-1,2,4-triazines. Oxidative aromatisation of these intermediates or auto-aromatisation of acylated (benzoyl chloride) at the NOH σ-adducts with elimination of benzoic acid gave the corresponding substituted 1,2,4-triazine 4-oxides or 1,2,4-triazines.

How to Cite
Kozhevnikov, D. N.; Kovalev, I. S.; Rusinov, V. L.; Chupakhin, O. N. Chem. Heterocycl. Compd. 2001, 37, 1136. [Khim. Geterotsikl. Soedin. 2001, 1239.]

For this article in the English edition, see DOI https://doi.org/10.1023/A:1013287918408

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Published

2001-09-25

Issue

No. 9 (2001)

Section

Original Papers