Isomerization of l,3-Diarylprop-2-yn-1-ols to Chalcones in the Presence of Potassium Hydroxide

摘要

Many methods have been developed for the isomerization of propargylic alcohols to enones or enals.Besides the isomerization by transition metals such as Pd,Ru,Rh,and Ir,several organic bases such as tributylamine and triton B have been introduced for such an isomerization.During the course of our ongoing studies on ruthenium-catalyzed synthesis of quinolines,we found that 3-(2-aminophenyl)-1-arylprop-2-yn-1-ols undergo a consecutive isomerization and cyclization under treatment of KOH to afford 2-arylquinolines (Scheme 1).This led us to investigate the isomerization of l,3-diarylprop-2-yn-l-ols under similar conditions.Herein we describe the isomerization to chalcones in the presence of KOH.