Russian Journal of Organic Chemistry

, Volume 46, Issue 6, pp 911–916 | Cite as

Regioselectivity in the amination of methylsulfanyl-substituted azines with O-mesitylenesulfonylhydroxylamine

  • G. I. Borodkin
  • A. Yu. Vorob’ev
  • M. M. Shakirov
  • V. G. Shubin


Reactions of O-mesitylenesulfonylhydroxylamine with 2-(methylsulfanyl)pyrazine, 2-(methylsulfanyl) pyrimidine, and 3,5-dimethyl-2-(methylsulfanyl)pyrimidines involve both sulfur and nitrogen atoms. The amination products at the sulfur atom prevail in the resulting mixture of isomeric cations, and the ratio of the S-NH2 and N-NH2 derivatives depends on the substrate nature. The experimental data were interpreted in terms of DFT quantum-chemical calculations.


Sulfur Atom Azine Dimethyl Sulfate Methylsulfanyl Anhydrous Calcium Chloride 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


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Copyright information

© Pleiades Publishing, Ltd. 2010

Authors and Affiliations

  • G. I. Borodkin
    • 1
    • 2
  • A. Yu. Vorob’ev
    • 1
    • 2
  • M. M. Shakirov
    • 1
  • V. G. Shubin
    • 1
  1. 1.Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian DivisionRussian Academy of SciencesNovosibirskRussia
  2. 2.Novosibirsk State UniversityNovosibirskRussia

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