Reactions of benzazole-2-thiones with 3,5-di-tert-butyl-4-hydroxybenzyl acetate |
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| Authors: | R. G. Tagasheva D. R. Gataullina I. F. Zaripova S. V. Bukharov G. N. Nugumanova T. R. Deberdeev Yu. K. Voronina |
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| Affiliation: | 1.Kazan National Research Technological University,Kazan, Tatarstan,Russia;2.Arbuzov Institute of Organic Chemistry, Kazan Research Center,Russian Academy of Sciences,Kazan, Tatarstan,Russia |
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| 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. |
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