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Cobalt(II)-Catalyzed C-H Alkylation of N-Heterocycles with 1,4-Dihydropyridines

Authors
Ghosh, PrithwishKwon, Na YeonByun, YoujungMishra, Neeraj KumarPark, Jung SuKim, In Su
Issue Date
Dec-2022
Publisher
AMER CHEMICAL SOC
Keywords
alkylation; cobalt; dihydropyridine; heterocycles; radical reaction
Citation
ACS CATALYSIS, v.12, no.24, pp 15707 - 15714
Pages
8
Journal Title
ACS CATALYSIS
Volume
12
Number
24
Start Page
15707
End Page
15714
URI
https://scholarworks.sookmyung.ac.kr/handle/2020.sw.sookmyung/152256
DOI
10.1021/acscatal.2c04741
ISSN
2155-5435
Abstract
The rapid incorporation of alkyl and acyl groups into C-H bonds of N-heterocycles is in demand for the development of lead candidates in drug discovery. Herein, we report the cobalt(II)-catalyzed C-H alkylation and acylation of N-heterocycles with 1,4-dihydropyridines (DHPs) as alkylating and acylating agents. Notably, a combination of KBrO3 and a Co(II) catalyst was successfully employed for the generation of alkyl and acyl radicals from DHPs. A series of heterocycles, including azauracils, quinoxalinones, pyrazinones, pyridones, quinolones, quinazolinones, xanthines, chromones, and azine N-oxides, were compatible under the developed conditions. The applicability of the developed protocol in challenging contexts is highlighted by the selective modification of drug candidates as well as the gram-scale synthesis of bioactive molecules. Combined mechanistic investigations aided the elucidation of a plausible reaction mechanism.
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