Metal- and Photocatalyst-Free, Visible-Light-Initiated C3 α‑Aminomethylation of Quinoxalin-2(1H)‑ones via Electron Donor–Acceptor Complexes

We report a metal- and photocatalyst-free C3 α-aminomethylation of quinoxalin-2­(1H)-ones with N-alkyl-N-methylanilines. The reaction proceeds through the formation of a photoactivated electron donor–acceptor complex between quinoxalin-2­(1H)-ones and N-alkyl-N-methylanilines. The present method pro...

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Veröffentlicht in:Journal of organic chemistry 2023-09, Vol.88 (18), p.13339-13350
Hauptverfasser: More, Devidas A., Shirsath, Sachin R., Muthukrishnan, M.
Format: Artikel
Sprache:eng
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Zusammenfassung:We report a metal- and photocatalyst-free C3 α-aminomethylation of quinoxalin-2­(1H)-ones with N-alkyl-N-methylanilines. The reaction proceeds through the formation of a photoactivated electron donor–acceptor complex between quinoxalin-2­(1H)-ones and N-alkyl-N-methylanilines. The present method provides a mild and environmentally friendly protocol that exhibits good atom economy and excellent functional group tolerance to obtain a library of biologically significant C3 α-aminomethylated quinoxalin-2­(1H)-ones in good yields.
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.3c01249