Transition-Metal-Free C‑3 Arylation of Quinoline-4-ones with Arylhydrazines

A transition-metal-free C-3-arylation of quinolin-4-ones in the presence of base has been achieved by using arylhydrazines as aryl radical source and air as oxidant. The reaction proceeds smoothly at room temperature and does not require any prefunctionalization and N-protection of quinoline-4-ones....

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Veröffentlicht in:Journal of organic chemistry 2015-05, Vol.80 (10), p.5369-5376
Hauptverfasser: Ravi, Makthala, Chauhan, Parul, Kant, Ruchir, Shukla, Sanjeev K, Yadav, Prem. P
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Sprache:eng
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Zusammenfassung:A transition-metal-free C-3-arylation of quinolin-4-ones in the presence of base has been achieved by using arylhydrazines as aryl radical source and air as oxidant. The reaction proceeds smoothly at room temperature and does not require any prefunctionalization and N-protection of quinoline-4-ones. The utility of this methodology is further demonstrated in synthesis of quinoline–quinolone hybrid as well as 6-aryl-benzofuro­[3,2-c]­quinoline scaffold.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.5b00739