P -toluenesulfonic acid-catalyzed synthesis of polysubstituted quinolines via Friedländer reaction under ball-milling conditions at room temperature and theoretical study on the mechanism using a density functional theory method

Abstract

The synthesis of polysubstituted quinolines was accomplished through Friedländer annulation between 2-aminoaryl ketones and different active methylene compounds at room temperature using ball-milling technique in the presence of p-toluenesulfonic acid. The mechanism of the reaction investigated by density functional theory-based modeling is also reported. This study aims at giving insight into the mechanism of the Friedländer reaction in the presence of acid catalysts. Copyright © 2014 John Wiley & Sons, Ltd.