Synthesis of 7-arylquinolinones and 6-arylindoles from 3-aminobiphenyls through regioselective cyclization reactions

7-Arylquinolinones were obtained in two steps from 3-aminobiphenyls through conversion into cinnamic amides. The highly regioselective cyclization under elimination of anisole proceeded in the presence of phosphoric acid and phosphorous pentoxide. 6-Arylindoles were accessible, although in lower yie...

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Bibliographic Details
Published in:Tetrahedron 2014-10, Vol.70 (43), p.8114-8121
Main Authors: Hammer, Sebastian G., Heinrich, Markus R.
Format: Article
Language:English
Subjects:
Aminobiphenyls
Cinnamic amides
Cyclizations
Heterocycles
Quinolinones
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Summary:7-Arylquinolinones were obtained in two steps from 3-aminobiphenyls through conversion into cinnamic amides. The highly regioselective cyclization under elimination of anisole proceeded in the presence of phosphoric acid and phosphorous pentoxide. 6-Arylindoles were accessible, although in lower yields, from 3-aminobiphenyls via 3-(biphenylamino)acrylates and palladium-catalyzed cyclization reactions. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2014.08.012