Potassium hydroxide/dimethyl sulfoxide promoted intramolecular cyclization for the synthesis of benzimidazol-2-ones

Astrid Beyer; Christine M M Reucher; Carsten Bolm

doi:10.1021/ol2008878

Potassium hydroxide/dimethyl sulfoxide promoted intramolecular cyclization for the synthesis of benzimidazol-2-ones

Org Lett. 2011 Jun 3;13(11):2876-9. doi: 10.1021/ol2008878. Epub 2011 May 2.

Authors

Astrid Beyer¹, Christine M M Reucher, Carsten Bolm

Affiliation

¹ Institute of Organic Chemistry, RWTH Aachen University, Aachen, Germany.

PMID: 21534616
DOI: 10.1021/ol2008878

Abstract

A new protocol for intramolecular N-arylations of ureas to form benzimidazol-2-ones has been developed. The cyclization reaction occurs in the presence of KOH and DMSO at close to ambient temperature. Under these conditions the yields are high and a wide range of functional groups are tolerated.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Benzimidazoles / chemical synthesis*
Benzimidazoles / chemistry
Catalysis
Cyclization
Dimethyl Sulfoxide / chemistry*
Hydroxides / chemistry*
Molecular Structure
Potassium Compounds / chemistry*
Urea / chemistry*

Substances

Benzimidazoles
Hydroxides
Potassium Compounds
benzimidazol-2-one
Urea
potassium hydroxide
Dimethyl Sulfoxide