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J Org Chem. 2019 Nov 1;84(21):14187-14201. doi: 10.1021/acs.joc.9b01844. Epub 2019 Sep 30.

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

Author information

1
Department of Organic Chemistry, Institute of Chemistry , University of Campinas, UNICAMP , Campinas , São Paulo 13083-970 , Brazil.
2
Structural Genomics Consortium, Nuffield Department of Medicine , University of Oxford , Old Road Campus Research Building, Roosevelt Drive , Oxford OX3 7DQ , United Kingdom.
3
Structural Genomics Consortium, Departamento de Genética e Evolução , Instituto de Biologia, UNICAMP , Campinas , São Paulo 13083-886 , Brazil.

Abstract

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.

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