Russian Journal of General Chemistry

, Volume 87, Issue 1, pp 22–28 | Cite as

Reactions of benzazole-2-thiones with 3,5-di-tert-butyl-4-hydroxybenzyl acetate

  • R. G. Tagasheva
  • D. R. Gataullina
  • I. F. Zaripova
  • S. V. Bukharov
  • G. N. Nugumanova
  • T. R. Deberdeev
  • Yu. K. Voronina
Article

Abstract

The benzylation of benzothiazole(oxazole, imidazole)-2-thiones with 3,5-di-tert-butyl-4-hydroxybenzyl acetate involves either the sulfur or nitrogen atom depending on the reaction conditions. The S- and N-benzylation products of benzazole-2-thiones are kinetically and thermodynamically controlled products, respectively. The use of 3,5-di-tert-butyl-4-hydroxy-benzyl acetate allows sterically hindered hydroxybenzyl derivatives of benzаzole-2-thiones to be generally synthesized under milder conditions than in known methods of their synthesis.

Keywords

sterically hindered phenols benzothiazole-2-thione oxazole-2-thione imidazole-2-thione benzylation 

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Copyright information

© Pleiades Publishing, Ltd. 2017

Authors and Affiliations

  • R. G. Tagasheva
    • 1
  • D. R. Gataullina
    • 1
  • I. F. Zaripova
    • 1
  • S. V. Bukharov
    • 1
  • G. N. Nugumanova
    • 1
  • T. R. Deberdeev
    • 1
  • Yu. K. Voronina
    • 2
  1. 1.Kazan National Research Technological UniversityKazan, TatarstanRussia
  2. 2.Arbuzov Institute of Organic Chemistry, Kazan Research CenterRussian Academy of SciencesKazan, TatarstanRussia

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