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

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.
Xiaoyu Yang 1,  Liang Wang 1 2,  Fangzhi Hu 1,  Lubin Xu 1,  Sanming Li 3,  Shuai-Shuai Li 1 2
Affiliations

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.

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