title: CuI-catalyzed aerobic oxidative α-aminaton cyclization of ketones to access aryl or alkenyl-substituted imidazoheterocycles.
abstract: CuI-catalyzed aerobic oxidative synthesis of imidazoheterocycles has been achieved. Four hydrogen atoms were removed in one step. This protocol was compatible with a broad range of functional groups, and it has been also successfully extended to unsaturated ketones, bringing about the formation of alkenyl-substituted imidazoheterocycles, which were difficult to prepare by previous means. Preliminary mechanistic studies indicated that this reaction was most likely to proceed through a catalytic Ortoleva-King reaction. By using this method, the marketed drug Zolimidine could be prepared with 90% yield on a gram scale from commercially available materials.
authors.affiliation: State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences , Fuzhou, Fujian 350002, China.
authors.forename: Yuanfei
authors.initials: Y
authors.lastname: Zhang
authors.forename: Zhengkai
authors.initials: Z
authors.lastname: Chen
authors.forename: Wenliang
authors.initials: W
authors.lastname: Wu
authors.forename: Yuhong
authors.initials: Y
authors.lastname: Zhang
authors.forename: Weiping
authors.initials: W
authors.lastname: Su
mesh_terms: D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D007454:Iodides / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction
chemical_list: D006571:Heterocyclic Compounds; D007093:Imidazoles; D007454:Iodides; D007659:Ketones; D003300:Copper; C073870:cuprous iodide