Modular synthesis of di- and trisubstituted imidazoles from ketones and aldehydes: a route to kinase inhibitors
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-...
| Main Authors: | , , , , |
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| Format: | Journal article |
| Language: | English |
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American Chemical Society
2019
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| _version_ | 1797054463830130688 |
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| author | De Toledo, I Grigolo, TA Bennett, JM Elkins, J Pilli, RA |
| author_facet | De Toledo, I Grigolo, TA Bennett, JM Elkins, J Pilli, RA |
| author_sort | De Toledo, I |
| collection | OXFORD |
| description | 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. |
| first_indexed | 2024-03-06T18:57:39Z |
| format | Journal article |
| id | oxford-uuid:12648292-ba92-4167-9aae-38a7cce35e42 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T18:57:39Z |
| publishDate | 2019 |
| publisher | American Chemical Society |
| record_format | dspace |
| spelling | oxford-uuid:12648292-ba92-4167-9aae-38a7cce35e422022-03-26T10:07:47ZModular synthesis of di- and trisubstituted imidazoles from ketones and aldehydes: a route to kinase inhibitorsJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:12648292-ba92-4167-9aae-38a7cce35e42EnglishSymplectic Elements at OxfordAmerican Chemical Society2019De Toledo, IGrigolo, TABennett, JMElkins, JPilli, RAA 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. |
| spellingShingle | De Toledo, I Grigolo, TA Bennett, JM Elkins, J Pilli, RA Modular synthesis of di- and trisubstituted imidazoles from ketones and aldehydes: a route to kinase inhibitors |
| title | Modular synthesis of di- and trisubstituted imidazoles from ketones and aldehydes: a route to kinase inhibitors |
| title_full | Modular synthesis of di- and trisubstituted imidazoles from ketones and aldehydes: a route to kinase inhibitors |
| title_fullStr | Modular synthesis of di- and trisubstituted imidazoles from ketones and aldehydes: a route to kinase inhibitors |
| title_full_unstemmed | Modular synthesis of di- and trisubstituted imidazoles from ketones and aldehydes: a route to kinase inhibitors |
| title_short | Modular synthesis of di- and trisubstituted imidazoles from ketones and aldehydes: a route to kinase inhibitors |
| title_sort | modular synthesis of di and trisubstituted imidazoles from ketones and aldehydes a route to kinase inhibitors |
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