Clay catalyzed conversion of isatoic anhydride † to 2-(o-aminophenyl)oxazolines

Abstract

A simple and environmentally safe procedure for the preparation of 2-(o-aminophenyl)oxazolines from isatoic anhydride is presented. A series of chiral derivatives of the title compound is prepared in moderate yield via natural kaolinitic clay catalyzed reactions with optically pure 2-aminoalcohols. Reaction of polymer-supported isatoic anhydride under these conditions with chiral 2-aminoalcohols proceeds to furnish polymer-anchored analogues.