Palladium-Catalyzed Multi-Component Reactions of N-Tosylhydrazones, 2-Iodoanilines and CO 2 towards 4-Aryl-2-Quinolinones

A palladium-catalyzed three-component reaction between N-tosylhydrazones, 2-iodoanilines and atmospheric pressure CO was developed whereby a tandem carbene migration insertion/lactamization strategy afforded 4-aryl-2-quinolinones in moderate to good yields. Notably, a wide range of functional groups...

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Veröffentlicht in:Chemistry : a European journal 2016-12, Vol.22 (52), p.18729-18732
Hauptverfasser: Sun, Song, Hu, Wei-Ming, Gu, Ning, Cheng, Jiang
Format: Artikel
Sprache:eng
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Zusammenfassung:A palladium-catalyzed three-component reaction between N-tosylhydrazones, 2-iodoanilines and atmospheric pressure CO was developed whereby a tandem carbene migration insertion/lactamization strategy afforded 4-aryl-2-quinolinones in moderate to good yields. Notably, a wide range of functional groups were tolerated in this procedure. This protocol features the simultaneous formation of four novel bonds; two C-C, one C=C and one C-N (amide), representing an efficient methodology for incorporation of CO into heterocycles.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201604256