Redox-Triggered Switchable Synthesis of 3,4-Dihydroquinolin-2(1<i>H</i>)-one Derivatives via Hydride Transfer/<i>N</i>-Dealkylation/<i>N</i>-Acylation

Abstract

The switchable synthesis of 3-non, 3-mono, 3,3'-disubstituted 3,4-dihydroquinolin-2(1<i>H</i>)-ones was developed through a redox-neutral hydride-transfer/<i>N</i>-dealkylation/<i>N</i>-acylation strategy from <i>o</i>-aminobenzaldehyde with 4-hydroxycoumarin, and Meldrum's acid, respectively. The unprecedented strategy for the synthesis of 3,3'-highly functionalized 3,4-dihydroquinolin-2(1<i>H</i>)-one has been realized with the in situ utilization of the released HCHO via the <i>o</i>-QM involved Michael addition. In addition, the synthetic utility of this protocol has been well illustrated via concise synthesis of CYP11B2 inhibitor.