Divergent g‑C3N4‑catalyzed Reactions of Quinoxalin-2(1H)‑ones with N‑Aryl Glycines under Visible Light: Solvent-Controlled Hydroaminomethylation and Annulation

An effective and simple visible light-induced heterogeneous g-C3N4-catalyzed decarboxylative reaction of quinoxalin-2­(1H)-ones with N-aryl glycines was developed. When the reaction was performed in DMSO/H2O and EtOH, the products dihydroquinoxalin-2­(1H)-ones and tetrahydroimidazo­[1,5-a]­quinoxali...

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Published inACS sustainable chemistry & engineering Vol. 8; no. 29; pp. 10740 - 10746
Main Authors Si, Ya-Feng, Chen, Xiao-Lan, Fu, Xiao-Yang, Sun, Kai, Song, Xiaojie, Qu, Ling-Bo, Yu, Bing
Format Journal Article
LanguageEnglish
Published American Chemical Society 27.07.2020
Subjects
catalysts
chemoselectivity
green chemistry
light
g-C3N4-catalyzed
visible light-induced
solvent-dependent system
decarboxylative reaction
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Summary:An effective and simple visible light-induced heterogeneous g-C3N4-catalyzed decarboxylative reaction of quinoxalin-2­(1H)-ones with N-aryl glycines was developed. When the reaction was performed in DMSO/H2O and EtOH, the products dihydroquinoxalin-2­(1H)-ones and tetrahydroimidazo­[1,5-a]­quinoxalin-4­(5H)-ones were unprecedentedly obtained in good yields, respectively. This solvent-dependent system offers advantages, including simple and easy operation, short reaction time, high chemoselectivity, a recyclable catalyst, metal-/base-/oxidant-free, and mild reaction conditions.
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ISSN:2168-0485
2168-0485
DOI:10.1021/acssuschemeng.0c02289