title: 4-Aryl-2-quinolones from 3,3-diarylacrylamides through intramolecular copper-catalyzed C-H functionalization/C-N bond formation.
abstract: Free NH 3,3-diarylacrylamides are cyclized to substituted 2-quinolones in the presence of CuI, PPh(3), and KO-t-Bu in o-xylene at 100 °C. The reaction proceeds through a C-H functionalization/C-N bond formation process. With unsymmetrical 3,3-diarylacrylamides, high selectivity is observed using substrates where the aromatic ring trans to the amide group bears o-methyl, -chloro, or -bromo substituents.
authors.affiliation: Dipartimento di Chimica e Tecnologie del Farmaco, La Sapienza, Università di Roma, P. le A. Moro 5, 00185 Rome, Italy.
authors.forename: Roberta
authors.initials: R
authors.lastname: Berrino
authors.forename: Sandro
authors.initials: S
authors.lastname: Cacchi
authors.forename: Giancarlo
authors.initials: G
authors.lastname: Fabrizi
authors.forename: Antonella
authors.initials: A
authors.lastname: Goggiamani
mesh_terms: D000577:Amides / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D006912:Hydroxyquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D007454:Iodides / Q000737:chemistry*; D015394:Molecular Structure; D015363:Quinolones / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000577:Amides; D006912:Hydroxyquinolines; D007454:Iodides; D015363:Quinolones; D003300:Copper; C073870:cuprous iodide; C010064:carbostyril