Reactions of Benzazole-2-thiones with 3,5-Di-tert-butyl-4-hydroxybenzyl Acetate

摘要

The benzylation of benzothiazole(oxazole, imidazole)-2-thiones with 3,5-di-tert-butyl-4-hydroxy-benzyl 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 benz.zole-2-thiones to be generally synthesized under milder conditions than in known methods of their synthesis.