Pd-Catalyzed Intramolecular Cyclization of 2-Iodoanilino Esters to Dihydroquinolin-4-ones

doi:10.1055/s-2007-992467

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Synfacts 2008(2): 0134-0134
DOI: 10.1055/s-2007-992467

Synthesis of Heterocycles

Pd-Catalyzed Intramolecular Cyclization of 2-Iodoanilino Esters to Dihydroquinolin-4-ones

Contributor(s): Victor Snieckus, Jignesh J. Patel
D. Solé*, O. Serrano
Universitat de Barcelona, Spain

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Publication History

Publication Date:
23 January 2008 (online)

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Significance

A palladium-catalyzed intramolecular cyclization of β-(2-iodoanilino)esters A to give dihydroquinolin-4-ones B is reported. K₃PO₄ along with Et₃N in toluene was found to be the effective combination for the intramolecular condensation, although under these conditions small amounts of hydrodehalogenation product C were detected in some cases. Carbamate (R² = CO₂Me) and sulfonamide (R² = Ts) failed to undergo cyclization and only gave reduced product C.