Cobalt salt-catalyzed carbocyclization reactions of α-bromo-N-phenylacetamide derivatives. Issue 9 (16th February 2017)

• Record Type: Journal Article
• Authors: Cheng, Yi-Chen; Chen, Ying-Yu; Chuang, Che-Ping
• Is Part Of: Organic & biomolecular chemistry. Volume 15:Issue 9(2017)
• Page Start: 2020
• Page End: 2032
• Publication Date: 2017-02-16
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c7ob00009j
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A Co(ii )-catalyzed carbocyclization reaction for the synthesis of 4-substituted quinolin-2-(1 H )-ones is described. Abstract : An efficient and low-cost method for the synthesis of 4-substituted quinolin-2-(1 H )-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-(1 H )-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-(1 H )-ones were formed effectively.