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

Xiaoyu Yang; Liang Wang; Fangzhi Hu; Lubin Xu; Sanming Li; Shuai-Shuai Li

doi:10.1021/acs.orglett.0c03863

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

Org Lett. 2021 Jan 15;23(2):358-364. doi: 10.1021/acs.orglett.0c03863. Epub 2020 Dec 23.

Authors

Xiaoyu Yang¹, Liang Wang^{1

2}, Fangzhi Hu¹, Lubin Xu¹, Sanming Li³, Shuai-Shuai Li^{1

2}

Affiliations

¹ College of Chemistry and Pharmaceutical Sciences, Qingdao Agricultural University, Changcheng Road #700, Qingdao 266109, PR China.
² College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Zhengzhou Road #53, Qingdao 266042, PR China.
³ School of Pharmacy, Shenyang Pharmaceutical University, Hongliu Road #85, Benxi 117004, PR China.

PMID: 33355465
DOI: 10.1021/acs.orglett.0c03863

Abstract

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

Publication types

Research Support, Non-U.S. Gov't