title: Cobalt salt-catalyzed carbocyclization reactions of α-bromo-N-phenylacetamide derivatives.
abstract: An efficient and low-cost method for the synthesis of 4-substituted quinolin-2-(1H)-ones has been developed. In the presence of TBHP, the cobalt(ii)-catalyzed carbocyclization reactions of arylethenyl substituted α-bromo-N-phenylacetamides, involving sequential 6-exo-trig radical cyclization, t-butylperoxy radical cross-coupling reaction and the base-promoted ionic Kornblum-DeLaMare reaction, produced 4-benzoylquinolin-2-(1H)-ones. A variety of useful functional groups such as methoxy, fluoro, chloro, bromo, methoxycarbonyl, and cyano groups, are compatible with the reaction conditions. This strategy was further applied to arylethynyl substituted α-bromo-N-phenylacetamides, and 4-benzylquinolin-2-(1H)-ones were formed effectively.
authors.affiliation: Department of Chemistry, National Cheng Kung University, Tainan, Taiwan 70101, Republic of China. cpchuang@mail.ncku.edu.tw.
authors.forename: Yi-Chen
authors.initials: YC
authors.lastname: Cheng
authors.affiliation: Department of Chemistry, National Cheng Kung University, Tainan, Taiwan 70101, Republic of China. cpchuang@mail.ncku.edu.tw.
authors.forename: Ying-Yu
authors.initials: YY
authors.lastname: Chen
authors.affiliation: Department of Chemistry, National Cheng Kung University, Tainan, Taiwan 70101, Republic of China. cpchuang@mail.ncku.edu.tw.
authors.forename: Che-Ping
authors.identifier: http://orcid.org/0000-0002-4514-7810
authors.initials: CP
authors.lastname: Chuang