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Chemistry of Heterocyclic Compounds

, Volume 46, Issue 12, pp 1476–1480 | Cite as

Oxidation mechanism of 6-methyl-2,4-dioxopyrimidine with selenium oxide and selenous acid

  • A. I. Rakhimov
  • R. B. Shulman
  • R. G. Fedunov
Article
  • 189 Downloads

Analysis of the oxidation mechanism of 6-methyl-2,4-dioxopyrimidine with selenium oxide and selenous acid with the formation of orotic aldehyde has been carried out by the ab initio quantum-chemical method on the 6-31G** basis. The mixed anhydride of acetic and selenous acids is formed with a gain of energy. It possesses high activity and steric accessibility in electrophilic attack on position 5 of the pyrimidine ring. The three-stage mechanism of the oxidation of the methyl group in 6-methyluracil by the mixed anhydride of selenous and acetic acids has been analyzed.

Keywords

selenium dioxide 6-methyluracil orotic aldehyde selenous acid 

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Copyright information

© Springer Science+Business Media, Inc. 2011

Authors and Affiliations

  • A. I. Rakhimov
    • 1
  • R. B. Shulman
    • 1
  • R. G. Fedunov
    • 2
  1. 1.Volgograd State Technical UniversityVolgogradRussia
  2. 2.Institute of Enviromental Chemical ProblemsRussian Academy of Natural SciencesVolgogradRussia

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