Electrochemical Synthesis of 2‑Aryl-3-(2-aminoaryl)quinoxalines via Oxidative Dearomatization/Ring-Opening/Cyclization Cascade Sequence of 2‑Arylindoles with 1,2-Diaminoarenes

A straightforward method has been developed to synthesize 2-aryl-3-(2-aminoaryl) quinoxalines from 2-arylindoles and 1,2-diaminoarenes under mild electrochemical conditions. The reaction proceeds through in situ generations of 2-arylindole-3-ones under electrochemical oxidative dearomatization of 2-...

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Veröffentlicht in:Journal of organic chemistry 2023-08, Vol.88 (15), p.11111-11121
Hauptverfasser: Nagare, Yadav Kacharu, Yadav, Jyothi, Dolas, Atul Jankiram, Shah, Imtiyaz Ahmad, Rangan, Krishnan, Choudhary, Rahul, Iype, Eldhose, Kumar, Indresh
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Sprache:eng
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Zusammenfassung:A straightforward method has been developed to synthesize 2-aryl-3-(2-aminoaryl) quinoxalines from 2-arylindoles and 1,2-diaminoarenes under mild electrochemical conditions. The reaction proceeds through in situ generations of 2-arylindole-3-ones under electrochemical oxidative dearomatization of 2-arylindoles, followed by a ring opening-cyclization sequence with 1,2-diaminoarenes. A series of 2-aryl-3-(2-aminoaryl) quinoxalines have been prepared with moderate to good yields (up to 75%).
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c01092