Visible-light mediated C-3 amination of quinoxalin-2(1H)-ones via electron donor-acceptor complexation

TitleVisible-light mediated C-3 amination of quinoxalin-2(1H)-ones via electron donor-acceptor complexation
Publication TypeJournal Article
Year of Publication2024
AuthorsMore, DA, Gayathri, PR, Thete, KR, Muthukrishnan, M
JournalAsian Journal of Organic Chemistry
Volume13
Issue8
Date PublishedAUG
Type of ArticleArticle
ISSN2193-5807
KeywordsC-3 amination, Dehydrogenative amination, EDA complex, quinoxalin-2(1H)-ones
Abstract

The formation of carbon-nitrogen bonds holds paramount importance in the realm of synthetic organic chemistry, finding extensive applications in the synthesis of pharmaceuticals, agrochemicals, and organic materials. Herein, we describe a novel EDA complex mediated, metal- and photocatalyst-free, visible-light-initiated direct C-3 amination of biologically important, quinoxalin-2(1H)-one moiety. The key to the success lies in the formation of a photoactivated electron donor-acceptor complex between quinoxalin-2(1H)-one and amine, which undergo subsequent electron transfer reaction to effect the desired transformation. A diverse array of 3-aminoquinoxalin-2(1H)-ones were prepared employing this process and the yields are up to 87%. This work represents a significant advancement toward a more environmentally friendly and efficient approach, characterized by mild reaction conditions and a high atom economy.

DOI10.1002/ajoc.202400150
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

2.7

Divison category: 
Organic Chemistry
Database: 
Web of Science (WoS)

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