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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
› InstitutsangabenFinancial support was received from National Natural Science Foundation of China (21907064, 22077080, and 22107068).
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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.

Key words

electrochemistry - dihydropyridine - anodic oxidation - radical addition - catalyst-free

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1737-2765.
  • Supporting Information


Publikationsverlauf

Eingereicht: 06. Dezember 2021

Angenommen nach Revision: 11. Januar 2022

Accepted Manuscript online:
11. Januar 2022

Artikel online veröffentlicht:
04. März 2022

© 2022. Thieme. All rights reserved

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