Efficient Access to Cyclic Ureas via Pd-Catalyzed Cyclization

Mark McLaughlin,* Michael Palucki, and Ian W. Davies
Department of Process Research, Merck Research Laboratories, P.O. Box 2000, Rahway, New Jersey 07065
Org. Lett., 2006, 8 (15), pp 3311–3314
DOI: 10.1021/ol061233j
Publication Date (Web): June 22, 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.

, mark_mclaughlin@merck.com

Abstract

Abstract Image

An efficient regioselective method for the preparation of structurally diverse imidazopyridinones and benzoimidazolones starting from readily available and economical starting materials is described. High-yielding reductive alkylation of electron-deficient o-haloarylamines followed by treatment with inexpensive N-chlorosulfonyl isocyanate afforded primary ureas in good overall yields. A Pd-catalyzed urea cyclization reaction furnished imidazopyridinones and benzoimidazolones in excellent yields. Overall, the developed chemistry provides rapid access to pharmaceutically important heterocyclic compounds with high efficiency.

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History

  • Published In Issue July 20, 2006
  • Received May 19, 2006

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