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Tandem Palladium-Catalyzed Urea Arylation-Intramolecular Ester Amidation: Regioselective Synthesis of 3-Alkylated 2,4-Quinazolinediones

Michael C. Willis,* Robert H. Snell, Anthony J. Fletcher and Robert L. Woodward

*Department of Chemistry, University of Bath, Bath, BA2 7AY, United Kingdom, Email: m.c.willisbath.ac.uk

M. C. Willis, R. H. Snell, A. J. Fletcher, R. L. Woodward, Org. Lett., 2006, 8, 5089-5091.

DOI: 10.1021/ol062009x


Abstract

A tandem palladium-catalyzed arylation-ester amidation sequence allows the synthesis of various quinazolinedione products by reaction of o-halo benzoates with monoalkyl ureas. The reactions are regioselective for the formation of 3-N-alkyl isomers.

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Key Words

quinazolinediones, Buchwald-Hartwig Coupling


ID: J54-Y2006-3510