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Modular synthesis of di- and trisubstituted imidazoles from ketones and aldehydes: a route to kinase inhibitors

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-i...

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Publication status:
Published
Peer review status:
Peer reviewed

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Publisher copy:
10.1021/acs.joc.9b01844

Authors


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Institution:
University of Oxford
Division:
MSD
Department:
NDM
Sub department:
Structural Genomics Consortium
Role:
Author
ORCID:
0000-0003-2858-8929
More by this author
Role:
Author
ORCID:
0000-0002-5919-7763
Publisher:
American Chemical Society
Journal:
Journal of Organic Chemistry More from this journal
Volume:
84
Issue:
21
Pages:
14187-14201
Publication date:
2019-08-28
Acceptance date:
2019-08-28
DOI:
EISSN:
1520-6904
ISSN:
0022-3263
Language:
English
Keywords:
Pubs id:
pubs:1059921
UUID:
uuid:12648292-ba92-4167-9aae-38a7cce35e42
Local pid:
pubs:1059921
Source identifiers:
1059921
Deposit date:
2019-10-06

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