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dc.contributor.authorRodrigues, Juliana M.
dc.contributor.authorCendón Mariño, Borja
dc.contributor.authorGulías Costa, Moisés
dc.contributor.authorMascareñas Cid, José Luis
dc.contributor.authorQueiroz, Maria João
dc.date.accessioned2021-07-20T11:50:19Z
dc.date.available2022-05-11T01:00:10Z
dc.date.issued2021
dc.identifier.citationJ. M. Rodrigues, B. Cendón, M. Gulías, J. L. Mascareñas, M.-J. R. P. Queiroz, Eur. J. Org. Chem. 2021, 2021, 3234.
dc.identifier.urihttp://hdl.handle.net/10347/26595
dc.descriptionThis is the peer reviewed version of the following article: J. M. Rodrigues, B. Cendón, M. Gulías, J. L. Mascareñas, M.-J. R. P. Queiroz, Eur. J. Org. Chem. 2021, 2021, 3234, which has been published in final form at https://doi.org/10.1002/ejoc.202100439. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions
dc.description.abstractIn the last decade, a number of metal-catalyzed technologies for the functionalization of C−H bonds in carbonaceous aromatic substrates have been developed. However, similar reactions with aza-heteroaromatic precursors are more challenging and have been much less developed. Herein, we report for the first time catalytic formal cycloadditions of N,S-heterocycles featuring carboxylic acid substituents, with unsaturated partners (alkynes). The reaction, which works with different symmetrical and unsymmetrical alkynes, produces appealing tricyclic ɑ-pyrones in a straightforward manner. The optimized conditions established for a model reaction employing thieno[2,3-b]pyridine-2-carboxylic acid as substrate, involved the use of Ag2CO3/AgSbF6 as additives, and proved to be general for different alkynes. Moreover, analogous cycloadditions using thieno[3,2-b]pyridine-2-carboxylic acid and thieno[2,3-b]pyrazine-6-carboxylic acid were successfully developed. Overall, this catalytic technology allows to build, in a single step, an interesting variety of pharmaceutically relevant tricyclic ɑ-pyrones exhibiting nitrogen and sulfur heteroatoms
dc.description.sponsorshipTo Fundação para a Ciência e Tecnologia (FCT) – Portugal financially supports CQUM (UID/QUI/686/2020), also financed by European Regional Development Fund (ERDF), COMPETE2020 and Portugal2020, the PT NMR network also supported by Portugal2020 and the PhD grant of J.M.R. (SFRH/BD/115844/2016) also financed by ESF (European Social Fund – North Portugal Regional Operational Programme) and HCOP (Human Capital Operational Programme). To COST Action CA15106 – C−H Activation in Organic Synthesis (CHAOS) – including a Short-Term Scientific Mission (STSM) grant attributed to J.M.R. to work in CiQUS. We also thank Spanish grants SAF2016-76689-R, PID2019-108624RB-I00, PID2019-110385GB-I00 and FPI fellowship BES-2017-079784 to B.C., the Consellería de Cultura, Educación e Ordenación Universitaria (ED431C 2017/19, 2015-CP082 and Centro Singular de Investigación de Galicia accreditation 2019–2022, ED431G 2019/03, the European Regional Development Fund (ERDF), and the European Research Council (Advanced Grant No. 340055)
dc.language.isoeng
dc.publisherWiley
dc.relationinfo:eu-repo/grantAgreement/EC/FP7/340055
dc.relationinfo:eu-repo/grantAgreement/FCT/POR_NORTE/SFRH%2FBD%2F115844%2F2016/PT
dc.relationinfo:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2019-108624RB-I00/ES/HERRAMIENTAS BASADAS EN METALES PARA SU USO EN QUIMICA BIOLOGICA Y BIOMEDICINA. DESARROLLO DE NUEVAS ESTRATEGIAS ANTICANCER
dc.relationinfo:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2019-110385GB-I00/ES/NUEVOS METODOS DE SINTESIS QUIMICA MEDIANTE LA FUNCIONALIZACION DE ENLACES C-H CON CATALIZADORES METALICOS
dc.relationinfo:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/BES-2017-079784/ES
dc.relationinfo:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/SAF2016-76689-R/ES
dc.rights© 2021 Wiley-VCH GmbH. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions
dc.subjectAnnulation
dc.subjectC−H Activation
dc.subjectN,S-heterocycles
dc.subjectRhodium catalysis
dc.subjectTricyclic ɑ-pyrones
dc.titleRhodium(III)-Catalyzed Formal Cycloaddition between Thienopyridine/Thienopyrazine Carboxylic Acids and Alkynes, Triggered by C−H Activation
dc.typeinfo:eu-repo/semantics/article
dc.identifier.DOI10.1002/ejoc.202100439
dc.relation.publisherversionhttps://doi.org/10.1002/ejoc.202100439
dc.type.versioninfo:eu-repo/semantics/acceptedVersion
dc.identifier.e-issn1099-0690
dc.rights.accessrightsinfo:eu-repo/semantics/embargoedAccess
dc.contributor.affiliationUniversidade de Santiago de Compostela. Centro de Investigación en Química Biolóxica e Materiais Moleculares
dc.contributor.affiliationUniversidade de Santiago de Compostela. Departamento de Química Orgánica
dc.description.peerreviewedSI


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