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A one-pot and modular approach to the synthesis of 2,4(5)-disubstituted imidazoles was developed based on ketone oxidation, employing catalytic HBr and DMSO, followed by imidazole condensation with aldehydes. This methodology afforded twenty-nine disubstituted NH-imidazoles (23%-85% yield). A three-step synthesis of 20 kinase inhibitors was achieved by employing this oxidation-condensation protocol, followed by bromination and Suzuki coupling in the imidazole ring to yield trisubstituted NH-imidazoles (23%-69%, three steps). This approach was also employed in the synthesis of known inhibitor GSK3037619A.

Original publication

DOI

10.1021/acs.joc.9b01844

Type

Journal article

Journal

The Journal of organic chemistry

Publication Date

11/2019

Volume

84

Pages

14187 - 14201

Addresses

Department of Organic Chemistry, Institute of Chemistry , University of Campinas, UNICAMP , Campinas , São Paulo 13083-970 , Brazil.

Keywords

Aldehydes, Ketones, Imidazoles, Protein Kinase Inhibitors, Oxidation-Reduction