Sequential Cu-catalyzed amidation-base-mediated camps cyclization: a two-step synthesis of 2-Aryl-4-quinolones from o-halophenones.
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.
Jones
Carrie P
CP
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Anderson
Kevin W
KW
Buchwald
Stephen L
SL
D000098:Acetophenones / Q000737:chemistry*; D001549:Benzamides / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D015363:Quinolones / Q000138:chemical synthesis* / Q000737:chemistry
D000098:Acetophenones; D001549:Benzamides; D007211:Indoles; D015363:Quinolones; C037689:benzamide; C013190:phenacyl bromide; D003300:Copper