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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

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

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de Toledo, Ian [1] ; Grigolo, Thiago [1] ; Bennett, James M. [2] ; Elkins, Jonathan M. [2, 3] ; Pilli, Ronaldo A. [1]
Total Authors: 5
[1] Univ Estadual Campinas, Inst Chem, Dept Organ Chem, UNICAMP, BR-13083970 Campinas, SP - Brazil
[2] Univ Oxford, Nuffield Dept Med, Struct Genom Consortium, Old Rd Campus Res Bldg, Roosevelt Dr, Oxford OX3 7DQ - England
[3] Univ Estadual Campinas, Dept Genet & Evolucao, Inst Biol, Struct Genom Consortium, BR-13083886 Campinas, SP - Brazil
Total Affiliations: 3
Document type: Journal article
Source: Journal of Organic Chemistry; v. 84, n. 21, p. 14187-14201, NOV 1 2019.
Web of Science Citations: 0

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. (AU)

FAPESP's process: 13/07607-8 - OCRC - Obesity and Comorbidities Research Center
Grantee:Licio Augusto Velloso
Support type: Research Grants - Research, Innovation and Dissemination Centers - RIDC
FAPESP's process: 19/13104-5 - Planning and synthesis of inhibitors based on biological targets: the case of neglected kinases
Grantee:Ronaldo Aloise Pilli
Support type: Regular Research Grants