Visible-Light Mediated C-3 Amination of Quinoxalin-2(1H)-ones via Electron Donor-Acceptor Complexation

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, vi...

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Bibliographic Details
Published inAsian journal of organic chemistry Vol. 13; no. 8
Main Authors More, Devidas A., Gayathri, P. R., Thete, Kishor R., Muthukrishnan, M.
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 01.08.2024
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
EDA complex
Quinoxalin-2(1H)-ones
Dehydrogenative amination
C-3 amination
DERIVATIVES
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Summary: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.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.202400150