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Copper-catalyzed intramolecular cyclization to N-substituted 1,3-dihydrobenzimidazol-2-ones. 2008

Zhaoguang Li, and Hongbin Sun, and Hualiang Jiang, and Hong Liu
Drug Discovery and Design Centre, State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Shanghai Institutes for Biological Sciences, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, China.

An efficient and convenient method was developed for preparing N-substituted 1,3-dihydrobenzimidazol-2-ones from N'-substituted N-(2-halophenyl)ureas via a CuI/DBU-catalyzed cyclization in DMSO under microwave heating. High yields were obtained and a variety of functional groups were tolerated under these conditions, including N'-aryl, alkyl, heterocyclic, various N-(substituted 2-halophenyl) and N-(2-iodopyridyl)ureas.

UI MeSH Term Description Entries
D007093 Imidazoles Compounds containing 1,3-diazole, a five membered aromatic ring containing two nitrogen atoms separated by one of the carbons. Chemically reduced ones include IMIDAZOLINES and IMIDAZOLIDINES. Distinguish from 1,2-diazole (PYRAZOLES).
D002384 Catalysis The facilitation of a chemical reaction by material (catalyst) that is not consumed by the reaction. Catalyses
D003300 Copper A heavy metal trace element with the atomic symbol Cu, atomic number 29, and atomic weight 63.55. Copper-63,Copper 63
D003500 Cyclization Changing an open-chain hydrocarbon to a closed ring. (McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Cyclizations
D001562 Benzimidazoles Compounds with a BENZENE fused to IMIDAZOLES.

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