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2-[(1E,3E)-4-Arylbuta-1,3-dien-1-yl]-4H-chromen-4-ones as dienes in Diels–Alder reactions: experimental and computational studies

2016Conference object Open access
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dc.contributor.authorAlbuquerque, Hélio
dc.contributor.authorSantos, Clementina M.M.
dc.contributor.authorLima, Carlos F.R.A.C.
dc.contributor.authorSantos, Luís M.N.B.F.
dc.contributor.authorCavaleiro, José
dc.contributor.authorSilva, Artur
dc.date.accessioned2017-09-21T11:28:37Z
dc.date.available2017-09-21T11:28:37Z
dc.date.issued2016
dc.description.abstractThe synthesis and reactivity of 2-[(1 £,3£)-4-arylbuta-1 ,3-dien-l-yl]-4H-chromen-4-ones 1 as dienes in Diets-Alder (DA) reactions towards several electron-poor and electron-rich dienophiles under microwave irradiation was studied. The optimized reaction conditions were achieved by using N-methylmaleimide2 as dienophile and Sc(0Tf)3 as Lewis acid under microwave-assisted and solvent-free conditions. The Lewis acid improved the reaction yields since it prevented the adducts obtained to undergo a second DA reaction, thus avoiding formation of a bisadduct. The a,~:y ,o-diene of the starting chromones showed to be the most reactive and the computational results confirmed the experimental findings. Theoretical calculations also allowed explaining some unexpected lack of reactivity by some dienophiles. The adducts prepared were dehydrogenated by using DDQ, however, the aza-adducts showed to be sensitive to the high energetic reaction conditions necessary to perform the aromatization.pt_PT
dc.description.sponsorshipThanks are due to University of Aveiro and FCT/MEC for the financial support of the QOPNA research unit (FCT UID/QUI/00062/2013) and CIQ-UP (Pest-C/QUI/UI0081/2013) through national founds and, where applicable, co-financed by the FEDER, within the PT2020 Partnership Agreement, and to the Portuguese NMR Network, as well as to the Instituto Politécnico de Bragança. H.M.T.A. and C.F.R.A.C.L. are grateful to FCT for their PhD (SFRH/BD/86277/2012) and Post-doc (SFRH/BPD/77972/2011) grants, respectively.pt_PT
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.citationAlbuquerque, Hélio; Santos, Clementina M.M.; Lima, Carlos F.R.A.C.; Santos, Luís M.N.B.F.; Cavaleiro, José; Silva, Artur (2016). 2-[(1E,3E)-4-Arylbuta-1,3-dien-1-yl]-4H-chromen-4-ones as dienes in Diels–Alder reactions: experimental and computational studies. In Terceiro Simposio Iberoamericano de Quimica Orgânica. Portopt_PT
dc.identifier.urihttp://hdl.handle.net/10198/14496
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.relationESTUDO CINÉTICO DE PROCESSOS DE TRANSIÇÃO DE FASE. INFLUÊNCIA DA SIMETRIA, FLEXIBILIDADE E ROTAÇÃO INTERNA MOLECULARES
dc.rights.urihttp://creativecommons.org/licenses/by-nd/4.0/pt_PT
dc.title2-[(1E,3E)-4-Arylbuta-1,3-dien-1-yl]-4H-chromen-4-ones as dienes in Diels–Alder reactions: experimental and computational studiespt_PT
dc.typeconference object
dspace.entity.typePublication
oaire.awardTitleESTUDO CINÉTICO DE PROCESSOS DE TRANSIÇÃO DE FASE. INFLUÊNCIA DA SIMETRIA, FLEXIBILIDADE E ROTAÇÃO INTERNA MOLECULARES
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/5876/UID%2FQUI%2F00062%2F2013/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/COMPETE/PEst-C%2FQUI%2FUI0081%2F2013/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/SFRH/SFRH%2FBD%2F86277%2F2012/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT//SFRH%2FBPD%2F77972%2F2011/PT
oaire.citation.conferencePlacePorto, Portugalpt_PT
oaire.citation.titleTerceiro Simposio Iberoamericano de Quimica Orgânicapt_PT
oaire.fundingStream5876
oaire.fundingStreamCOMPETE
oaire.fundingStreamSFRH
person.familyNameSantos
person.givenNameClementina M.M.
person.identifier.ciencia-id9018-DB9C-C590
person.identifier.orcid0000-0003-4380-7990
person.identifier.scopus-author-id7201458663
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
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project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
rcaap.rightsopenAccesspt_PT
rcaap.typeconferenceObjectpt_PT
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