title: A general copper powder-catalyzed Ullmann-type reaction of 3-halo-4(1H)-quinolones with various nitrogen-containing nucleophiles.
abstract: 3-(N-Substituted) 4(1H)-quinolinones were synthesized using the copper-catalyzed Ullmann C-N bond forming strategy in moderate to quantitative yields. Starting from 3-halo-4(1H)-quinolones, various nucleophiles including amides, lactams, sulfonamides and NH-containing azoles have been used successfully. In all cases, the reactions take place rapidly in toluene and proceed by using copper powder as a catalyst, DMEDA as a ligand and K(2)CO(3) as a base. In addition, other related heterocycles such as 3-bromoquinolin-2(1H)-ones, 3-bromocoumarin, and 3,5-dibromo-2-pyridone show good to very high reactivity with various nucleophiles under our Cu/DMEDA catalyst system.
authors.affiliation: 1Univ Paris-Sud, 2CNRS, BioCIS UMR 8076, Laboratoire de Chimie Thérapeutique, Faculté de Pharmacie, 5 rue J.-B. Clément, Châtenay-Malabry, F-92296, France.
authors.forename: Davide
authors.initials: D
authors.lastname: Audisio
authors.forename: Samir
authors.initials: S
authors.lastname: Messaoudi
authors.forename: Jean-François
authors.initials: JF
authors.lastname: Peyrat
authors.forename: Jean-Daniel
authors.initials: JD
authors.lastname: Brion
authors.forename: Mouâd
authors.initials: M
authors.lastname: Alami
mesh_terms: D000586:Amination; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D015394:Molecular Structure; D017672:Nitrogen Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry; D015363:Quinolones / Q000737:chemistry*
chemical_list: D017672:Nitrogen Compounds; D015363:Quinolones; D010165:Palladium; D003300:Copper