Copper-Catalyzed Aza-Michael Addition of 2-Aminobenzoate to β-Substituted α,β-Unsaturated Ketones: One-Pot Synthesis of 3-Carbonyl-2-Substituted Quinolin-4(1H)-ones

J Org Chem. 2018 Mar 2;83(5):2694-2705. doi: 10.1021/acs.joc.7b03162. Epub 2018 Feb 9.

Abstract

We present a new and straightforward one-pot process for the synthesis of 3-carbonyl-4-quinolone derivatives through highly efficient Cu-catalyzed aza-Michael addition of 2-aminobenzoates to β-substituted α,β-unsaturated ketones/cyclization/mild oxidation reactions. A broad range of new versatile 3-carbonyl-quinolin-4(1H)-ones is prepared from readily available chemicals under mild reaction conditions with short reaction times, producing good to excellent yields (up to 99%).

Publication types

  • Research Support, Non-U.S. Gov't