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Synfacts 2011(3): 0261-0261
DOI: 10.1055/s-0030-1259571
DOI: 10.1055/s-0030-1259571
Synthesis of Heterocycles
© Georg Thieme Verlag
Stuttgart ˙ New York
Palladium-Catalyzed Heteroannulation Route to Benzazepinones
H. Cao, T. O. Vieira, H. Alper*
University of Ottawa, Canada
Further Information
Publication History
Publication Date:
16 February 2011 (online)
Significance
Reported is a method for the synthesis of benzazepinone derivatives 3 by the hydroamination of the Baylis-Hillman acetate 1 with amines 2, followed by intramolecular cyclocarbonylation of the resulting allylamines under palladium catalysis. After screening of ligands and bases, the optimized conditions were found to require an excess of amine 2, 100 psi of CO, and Pd(OAc)2/dppb as catalyst. The reaction was extended to a series of amines. Although both aromatic and aliphatic amines were found to be active for the reactions, the latter afforded lower yields of products than the former systems. Substituents R¹, R² and R³ have a modest effect on the yield, but yields are higher when R² = EDGs.