One-Pot Synthesis of Quinolin-4(1H)-one Derivatives by a Sequential Michael Addition–Elimination/Palladium-Catalyzed Buchwald–Hartwig Amination Reaction

Abstract

A convenient approach has been developed for the construction of quinolin-4(1<i>H</i>)-one frameworks, starting from (<i>Z</i>)-β-chlorovinyl aromatic ketones and amines. Intermolecular Michael addition of an amine to a (<i>Z</i>)-β-chlorovinyl ketone was followed by elimination of a chloride anion to give enamine intermediates, with full retention of the initial <i>Z</i>-configuration. The enamine intermediates were transformed into quinolin-4(1<i>H</i>)-one products by a palladium-catalyzed intramolecular N-arylation in a tandem one-pot manner, with good to excellent yields.