Synfacts 2008(2): 0134-0134  
DOI: 10.1055/s-2007-992467
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

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
Further Information

Publication History

Publication Date:
23 January 2008 (online)


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.