Oxalyl boronates enable modular synthesis of bioactive imidazoles
Described herein is the preparation of oxalyl boronate building blocks and their application for the construction of heterocycles. The oxalyl unit, readily accessible through commercially available starting materials, enables a modular approach for the synthesis of imidazoles. A variety of aromatic,...
| Main Authors: | , , , , , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
Wiley
2017
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| _version_ | 1797079635611090944 |
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| author | Lee, C Holownia, A Bennett, J Elkins, J St Denis, J Adachi, S Yudin, A |
| author_facet | Lee, C Holownia, A Bennett, J Elkins, J St Denis, J Adachi, S Yudin, A |
| author_sort | Lee, C |
| collection | OXFORD |
| description | Described herein is the preparation of oxalyl boronate building blocks and their application for the construction of heterocycles. The oxalyl unit, readily accessible through commercially available starting materials, enables a modular approach for the synthesis of imidazoles. A variety of aromatic, heteroaromatic, and alkyl carboxaldehydes were condensed with oxalyl boronates to afford substituted boryl imidazoles in a regiocontrolled fashion. Subsequent palladium-catalyzed cross-coupling with haloarenes furnished the desired trisubstituted imidazole scaffolds. To demonstrate the utility of these scaffolds, potent inhibitors of the serine/threonine-protein kinase STK10 were synthesized. |
| first_indexed | 2024-03-07T00:48:43Z |
| format | Journal article |
| id | oxford-uuid:859d7d70-a6a0-4a34-af71-44894cac8fd1 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T00:48:43Z |
| publishDate | 2017 |
| publisher | Wiley |
| record_format | dspace |
| spelling | oxford-uuid:859d7d70-a6a0-4a34-af71-44894cac8fd12022-03-26T21:58:41ZOxalyl boronates enable modular synthesis of bioactive imidazolesJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:859d7d70-a6a0-4a34-af71-44894cac8fd1EnglishSymplectic Elements at OxfordWiley2017Lee, CHolownia, ABennett, JElkins, JSt Denis, JAdachi, SYudin, ADescribed herein is the preparation of oxalyl boronate building blocks and their application for the construction of heterocycles. The oxalyl unit, readily accessible through commercially available starting materials, enables a modular approach for the synthesis of imidazoles. A variety of aromatic, heteroaromatic, and alkyl carboxaldehydes were condensed with oxalyl boronates to afford substituted boryl imidazoles in a regiocontrolled fashion. Subsequent palladium-catalyzed cross-coupling with haloarenes furnished the desired trisubstituted imidazole scaffolds. To demonstrate the utility of these scaffolds, potent inhibitors of the serine/threonine-protein kinase STK10 were synthesized. |
| spellingShingle | Lee, C Holownia, A Bennett, J Elkins, J St Denis, J Adachi, S Yudin, A Oxalyl boronates enable modular synthesis of bioactive imidazoles |
| title | Oxalyl boronates enable modular synthesis of bioactive imidazoles |
| title_full | Oxalyl boronates enable modular synthesis of bioactive imidazoles |
| title_fullStr | Oxalyl boronates enable modular synthesis of bioactive imidazoles |
| title_full_unstemmed | Oxalyl boronates enable modular synthesis of bioactive imidazoles |
| title_short | Oxalyl boronates enable modular synthesis of bioactive imidazoles |
| title_sort | oxalyl boronates enable modular synthesis of bioactive imidazoles |
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