Utilize este identificador para referenciar este registo:
https://hdl.handle.net/1822/81239
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Campo DC | Valor | Idioma |
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dc.contributor.author | Pedroso de Lima, Fabio | por |
dc.contributor.author | Lence, Emilio | por |
dc.contributor.author | Suarez de Cepeda, Pilar | por |
dc.contributor.author | Correia, Carla | por |
dc.contributor.author | Carvalho, M. Alice | por |
dc.contributor.author | Gonzalez-Bello, Concepcion | por |
dc.contributor.author | Proença, M. Fernanda R. P. | por |
dc.date.accessioned | 2022-12-19T09:51:37Z | - |
dc.date.issued | 2022-06-24 | - |
dc.identifier.citation | Pedroso de Lima, F., Lence, E., Suárez de Cepeda, P., Correia, C., Carvalho, M. A., González-Bello, C., & Proença, M. F. (2022). Regioselective Synthesis of 2-Aryl-5-cyano-1-(2-hydroxyaryl)-1H-imidazole-4-carboxamides Self-Assisted by a 2-Hydroxyaryl Group. ACS Omega, 7(27), 23289-23301. doi: 10.1021/acsomega.2c01399 | por |
dc.identifier.issn | 2470-1343 | por |
dc.identifier.uri | https://hdl.handle.net/1822/81239 | - |
dc.description.abstract | The reactivity of the diaminomaleonitrile-based imines containing hydroxyphenyl substituents with diverse aromatic aldehydes has been explored for the synthesis of novel highly substituted nitrogen heterocycles, which are considered privileged scaffolds in drug discovery. We report here a simple and efficient method for the regiocontrolled synthesis of a variety of 2-aryl-5cyano-1-(2-hydroxyaryl)-1H-imidazole-4-carboxamides from 2-hydroxybenzylidene imines and aromatic aldehydes. Computational studies on the reaction path revealed that the regioselectivity of the reaction toward the formation of imidazole derivatives instead of 1,2-dihydropyrazines, most likely via a diaza-Cope rearrangement, is driven by the 2-hydroxyaryl group in the scaffold. The latter group promotes the intramolecular abstraction and protonation process in the cycloadduct intermediate, triggering the evolution of the reaction toward the formation of imidazole derivatives. | por |
dc.description.sponsorship | Financial support from Axencia Galega de Innovación (2020-PG067, CG-B), Programa NORTE 2020─CCDR-N (ref. NORTE-08-5369-FSE-000033, MFP), the Spanish Ministry of Science and Innovation (PID2019-105512RB-I00, CG-B), the Xunta de Galicia [ED431C 2021/29 and the Centro singular de investigación de Galicia accreditation 2019–2022 (ED431G 2019/03), CG-B], and the European Regional Development Fund (ERDF) is gratefully acknowledged. All authors thank the Centro de Supercomputación de Galicia (CESGA) for the use of the Finis Terrae computer. | por |
dc.language.iso | eng | por |
dc.publisher | American Chemical Society | por |
dc.rights | restrictedAccess | por |
dc.title | Regioselective synthesis of 2-Aryl-5-cyano-1-(2-hydroxyaryl)-1H-imidazole-4-carboxamides self-assisted by a 2-Hydroxyaryl group | por |
dc.type | article | - |
dc.peerreviewed | yes | por |
dc.relation.publisherversion | https://pubs.acs.org/doi/10.1021/acsomega.2c01399 | por |
oaire.citationStartPage | 23289 | por |
oaire.citationEndPage | 23301 | por |
oaire.citationIssue | 27 | por |
oaire.citationVolume | 7 | por |
dc.date.updated | 2022-12-17T23:19:24Z | - |
dc.identifier.doi | 10.1021/acsomega.2c01399 | por |
dc.date.embargo | 10000-01-01 | - |
dc.subject.wos | Science & Technology | - |
sdum.export.identifier | 12416 | - |
sdum.journal | ACS Omega | por |
Aparece nas coleções: | CDQuim - Artigos (Papers) |
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Ficheiro | Descrição | Tamanho | Formato | |
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acsomega.2c01399.pdf Acesso restrito! | 2,93 MB | Adobe PDF | Ver/Abrir |