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
Article
  • 72 Downloads

Abstract

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.

Keywords

Sulfur Atom Azine Dimethyl Sulfate Methylsulfanyl Anhydrous Calcium Chloride 

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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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