title: Synthesis of 2-Aminoazoles from Thioesters via α-Heterosubstituted Ketones by Copper-Mediated Cross-Coupling.
abstract: Facile synthesis of a variety of α-heterosubstituted ketones under mild conditions was achieved by copper-mediated cross-coupling of thioesters with functionalized organostannanes. Application of this coupling methodology provided a concise pathway for the conversion of carboxylic acids to 2-aminoimidazoles, 2-aminothiazoles, and 2-aminooxazoles via thioesters in practical yields.
authors.affiliation: Daiichi Sankyo Co., Ltd. , 1-2-58 Hiromachi, Shinagawa-ku, Tokyo 140-8710, Japan.|Department of Chemistry and Biochemistry, University of California , Santa Barbara, California 93106, United States.
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Kobayashi
authors.affiliation: Department of Chemistry and Biochemistry, University of California , Santa Barbara, California 93106, United States.
authors.forename: John A
authors.initials: JA
authors.lastname: Eickhoff
authors.affiliation: Department of Chemistry and Biochemistry, University of California , Santa Barbara, California 93106, United States.
authors.forename: Armen
authors.initials: A
authors.lastname: Zakarian
mesh_terms: D001393:Azoles / Q000138:chemical synthesis* / Q000737:chemistry; D003300:Copper / Q000737:chemistry*; D004952:Esters / Q000737:chemistry*; D007093:Imidazoles / Q000138:chemical synthesis / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D013844:Thiazoles / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: C518811:2-aminooxazole; D001393:Azoles; D004952:Esters; D007093:Imidazoles; D007659:Ketones; D010080:Oxazoles; D013438:Sulfhydryl Compounds; D013844:Thiazoles; C004483:2-aminothiazole; C014973:2-aminoimidazole; D003300:Copper