title: Copper-catalyzed [5+1] annulation of 2-ethynylanilines with an N,O-acetal leading to construction of quinoline derivatives.
abstract: A novel copper-catalyzed [5 + 1] annulation of 2-ethynylanilines with an N,O-acetal, which functioned as a C1 part, leading to the preparation of quinoline derivatives with an ester substituent on the 2-position is described. A combination of CuBr(2) and trifluoroacetic acid (TFA) promoting [5 + 1] annulation of the 2-ethynylaniline with ethyl glyoxylate is also demonstrated.
authors.affiliation: Department of Pure and Applied Chemistry, Faculty of Science and Technology, Tokyo University of Science (RIKADAI), Noda, Chiba 278-8510, Japan. sakachem@rs.noda.tus.ac.jp
authors.forename: Norio
authors.initials: N
authors.lastname: Sakai
authors.forename: Kosuke
authors.initials: K
authors.lastname: Tamura
authors.forename: Kazuyori
authors.initials: K
authors.lastname: Shimamura
authors.forename: Reiko
authors.initials: R
authors.lastname: Ikeda
authors.forename: Takeo
authors.initials: T
authors.lastname: Konakahara
mesh_terms: D000080:Acetals / Q000737:chemistry*; D000114:Acetylene / Q000031:analogs & derivatives* / Q000737:chemistry; D000814:Aniline Compounds / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D006038:Glyoxylates / Q000737:chemistry; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*; D010100:Oxygen / Q000737:chemistry*; D011804:Quinolines / Q000737:chemistry*
chemical_list: C483919:2-ethynylaniline; D000080:Acetals; D000814:Aniline Compounds; D006038:Glyoxylates; D011804:Quinolines; D003300:Copper; C037219:quinoline; C031150:glyoxylic acid; D009584:Nitrogen; D000114:Acetylene; D010100:Oxygen