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Synfacts 2008(4): 0350-0350  
DOI: 10.1055/s-2008-1042862
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Indolylquinolin-2-ones via a Cross-Coupling-Cyclization Sequence

Contributor(s): Victor Snieckus, Jignesh J. Patel
Z. Wang, J. Wu*
Fudan University and Shanghai Institute of Organic Chemistry, P. R. of China
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Publication History

Publication Date:
19 March 2008 (online)

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Significance

Reported is a synthetic route to 1H-indol-2-yl-(4-aryl)-quinolin-2(1H)-ones via sequential Pd-catalyzed Sonogashira-Castro-Stephens reactions of the intermediate 4-aryl-3-bromoquinolones which, in turn, are obtained by chemoselective Suzuki-Miyaura cross-coupling of the corresponding 4-triflate derivatives. The Sonogashira-Castro-Stephens sequence was carried out in one pot except in one case where the intermediate alkyne was isolated.