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 (SN H) 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.
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Kozhevnikov, Kovalev, I.S., Rusinov, V.L. et al. Reactions of 1,2,4-Triazines with Nucleophiles. 6. Use of SNH Methodology for the Direct Introduction of Cyclic Diketone Residue into the 1,2,4-Triazine Ring FORENAME = D. N.. Chemistry of Heterocyclic Compounds 37, 1136–1140 (2001). https://doi.org/10.1023/A:1013287918408
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DOI: https://doi.org/10.1023/A:1013287918408