Organic Letters 2006-07-20

Efficient access to cyclic ureas via Pd-catalyzed cyclization.

Mark McLaughlin, Michael Palucki, Ian W Davies

Index: Org. Lett. 8 , 3311, (2006)

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Abstract

[Structure: see text] 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.