Synthesis 2022; 54(11): 2696-2706
DOI: 10.1055/a-1737-2765
paper

Radical Addition of 4-Hydroxyquinazolines and Alkylation of Quinones by the Electro-Induced Homolysis of 4-Alkyl-1,4-di­hydropyridines

Xiaosheng Luo
a   Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Frontiers Science Center for Transformative Molecules, Shanghai Jiao Tong University, Shanghai 200240, P. R. of China
,
Qiping Feng
b   Department of Orthodontics, Shanghai Ninth People’s Hospital, Shanghai Jiao Tong University School of Medicine; College of Stomatology, Shanghai Jiao Tong University; National Center for Stomatology; National Clinical Research Center for Oral Diseases; Shanghai Key Laboratory of Stomatology; Research Unit of Oral and Maxillofacial Regenerative Medicine, Chinese Academy of Medical Sciences, Shanghai 200011, P. R. of China
,
Ping Wang
a   Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Frontiers Science Center for Transformative Molecules, Shanghai Jiao Tong University, Shanghai 200240, P. R. of China
› Author Affiliations
Financial support was received from National Natural Science Foundation of China (21907064, 22077080, and 22107068).


Abstract

The formation of C(sp3)-centered radicals via the electro-­induced homolysis of 4-alkyl-1,4-dihydropyridines (alkyl-DHPs) is reported. The resulting alkyl radicals reacted with 4-hydroxyquinazolines or quinones to afford 2-alkyldihydroquinazolinones or alkylated quinones. A broad range of alkyl DHPs could be used as versatile radical precursors under electrolysis conditions. This alterative strategy provided a simple and effective pathway for the construction of C(sp2)–C(sp3) and C(sp3)–C(sp3) bonds under mild conditions.

Supporting Information



Publication History

Received: 06 December 2021

Accepted after revision: 11 January 2022

Accepted Manuscript online:
11 January 2022

Article published online:
04 March 2022

© 2022. Thieme. All rights reserved

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Rüdigerstraße 14, 70469 Stuttgart, Germany

 
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