A direct two-step method for the preparation of 2-aryl- and 2-vinyl-4-quinolones that utilizes a copper-catalyzed amidation of o-halophenones followed by a base-promoted Camps cyclization of the resulting N-(2-ketoaryl)amides is described. With CuI, a diamine ligand, and base as the catalyst system, the amidation reactions proceed in good yields for a range of aryl, heteroaryl, and vinyl amides. The subsequent Camps cyclization efficiently provides the desired 4-quinolones with the conditions that are described.
“Sequential Cu-Catalyzed Amidation-Base-Mediated Camps Cyclization: A Two-Step Synthesis of 2-Aryl-4-quinolones fromo-Halophenones”, J. Org. Chem., 2007, 72(21), 7968-7973.