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Synfacts 2007(2): 0140-0140  
DOI: 10.1055/s-2006-955823
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Pd-Catalyzed C-N Coupling. Synthesis of 2,4-Quinazolinediones

Contributor(s): Victor Snieckus, Yigang Zhao
M. C. Willis*, R. H. Snell, A. J. Fletcher, R. L. Woodward
University of Bath, UK
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Publication History

Publication Date:
23 January 2007 (online)

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Significance

Starting with readily available o-bromobenzoates and monoalkyl ureas, a one-step, two C-N bond-forming process to 3-alkylated 2,4-quinazolinedinones is reported. The tandem reaction involves a Pd-catalyzed, regioselective arylation of a monoalkyl urea followed by an intramolecular amidation and proceeds in good to excellent yields with a relatively broad range of R1 and R2 substitution patterns.