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Modular Synthesis of Di- and Trisubstituted Imidazoles from Ketones and Aldehydes: A Route to Kinase Inhibitors

Ian de Toledo, Thiago A. Grigolo, James M. Bennett, Jonathan M. Elkins and Ronaldo A. Pilli*

*Department of Organic Chemistry, Institute of Chemistry, University of Campinas, UNICAMP, Campinas, São Paulo 13083-970, Brazil, Email: rapilliunicamp.br

I. de Toledo, T. A. Grigolo, J. M. Bennett, J. M. Elkins, R. A. Pilli, J. Org. Chem., 2019, 84, 14187-14201.

DOI: 10.1021/acs.joc.9b01844 (free Supporting Information)


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Abstract

A ketone oxidation, employing catalytic HBr and DMSO, followed by imidazole condensation with aldehydes provides 2,4(5)-disubstituted imidazoles in good yields. A three-step synthesis of 20 kinase inhibitors was achieved by employing this oxidation-condensation protocol, followed by bromination and Suzuki coupling.

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Note

Heteroaromatic methylketones (indole and pyridine derivatives) require some adjustment of the experimental conditions, but can be used.

Ronaldo A. Pilli, July 11, 2020


Key Words

Imidazoles, DMSO


ID: J42-Y2019