Synthesis of some new substituted oxiranes from 4'-hydroxy-3',5'-dinitrochalcones and their sulfanilic acid-catalyzed aminolysis

A new series of (4'-hydroxy-3',5'-dinitrophenyl) (3-aryloxiran-2-yl) methanone derivatives has been synthesized by the reaction of 4'-hydroxy-3',5'-dinitro-substituted chalcones and alkaline H2O2. The resulted oxiranes on sulfanilic acid-catalyzed aminolysis afforded 2-hydroxy-1-(4'-hydroxy-3',5'-dinitrophenyl)-3-aryl-3-(arylamino) propan-1-one derivatives. The advantage of this environmentally benign safe protocol offers a simple reaction set-up, mild reaction conditions, high product yields and short reaction time. The catalyst was reused several times without significant loss of catalytic activity.