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
Org. Lett., 2006, 8 (22), pp 5089–5091
DOI: 10.1021/ol062009x
Publication Date (Web): September 26, 2006
Copyright © 2006 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, m.c.willis@bath.ac.uk

Abstract

Abstract Image

o-Halo benzoates can be combined with monoalkyl ureas in a tandem palladium-catalyzed arylation−ester amidation sequence to deliver quinazolinedione products. The reactions are regioselective for formation of the 3-N-alkyl isomers. Significant variation of both coupling partners is possible, allowing the synthesis of a diverse array of substituted quinazolinediones, exemplified by the preparation of a simple unsymmetric-dialkylated natural product.

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History

  • Published In Issue October 26, 2006
  • Received August 14, 2006

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