Repository logo
 
Publication

Chromone derivatives as novel dienes in Diels-Alder reactions

2016Conference object Open access
Simple item page
dc.contributor.authorAlbuquerque, Hélio
dc.contributor.authorSantos, Clementina M.M.
dc.contributor.authorLima, C.F.R.A.C.
dc.contributor.authorSantos, L.M.N.B.F.
dc.contributor.authorCavaleiro, José
dc.contributor.authorSilva, Artur
dc.date.accessioned2017-11-09T12:26:50Z
dc.date.available2017-11-09T12:26:50Z
dc.date.issued2016
dc.description.abstractChromones are a group of heterocyclic compounds widespread in Nature and an interesting scaffold because they have been involved in a range of chemical transformations [1]. Following our previous studies on Diels‒Alder (DA) reactions of chromone derivatives [2], novel 2-[(1E,3E)-4-arylbuta-1,3-dien- 1-yl]-4H-chromen-4-ones 1 were synthesized to further study the reactivity of their two diene systems (α,β:γ,δ versus 2,3:α,β) in DA reactions (Fig.1). A series of dienophiles were reacted with chromones 1 under microwave-assisted conditions. The best yields of adducts 2 were achieved using N-methylmaleimide as dienophile and Sc(OTf)3 as Lewis acid in solvent-free conditions. The crucial role of Sc(OTf)3 relies on the chelation with carbonyl group of adducts 2 avoiding both the occurrence of a second DA reaction and the formation of bisadducts 6. The α,β:γ,δ-diunsaturated system of chromones 1 showed to be the most reactive diene for maleimides, dicarboxylates and azo-dicarboxylates, affording adducts 2, 4 and 5, respectively. Adducts 2 were dehydrogenated to the corresponding flavone derivatives 3 using DDQ as oxidizing agent (Fig.1). Computational calculations confirmed the experimental findings on DA reactions and helped to explain the unexpected lack of reactivity of some dienophiles. All the experimental procedures and extensive 1D and 2D NMR characterization of the final adducts and intermediates will be presented and discussed.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, cofinanced 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, CFRAC; Santos, LMNBF; Cavaleiro, José; Silva, Artur (2016). Chromone derivatives as novel dienes in Diels-Alder reactions. In XXII Encontro Luso-Galego de Química. Bragança: Sociedade Portuguesa de Química. ISBN 978-989-8124-17-3pt_PT
dc.identifier.isbn978-989-8124-17-3
dc.identifier.urihttp://hdl.handle.net/10198/14612
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-nc/4.0/pt_PT
dc.titleChromone derivatives as novel dienes in Diels-Alder reactionspt_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.conferencePlaceBragança, Portugalpt_PT
oaire.citation.titleXXII Encontro Luso-Galego de Químicapt_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
project.funder.identifierhttp://doi.org/10.13039/501100001871
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
relation.isAuthorOfPublication64f662b6-775d-4ea0-bfd7-f527af0ac1a0
relation.isAuthorOfPublication.latestForDiscovery64f662b6-775d-4ea0-bfd7-f527af0ac1a0
relation.isProjectOfPublicationa955d531-2af9-40df-baaf-a064d8a697e9
relation.isProjectOfPublicationff214ec3-9b06-4f7f-b506-e3620a9788d6
relation.isProjectOfPublicationb1a3433a-76f8-4132-b2c2-8f3aeeb902e2
relation.isProjectOfPublicationf06a88e3-f71e-4186-b4e7-87f005a827dc
relation.isProjectOfPublication.latestForDiscoveryf06a88e3-f71e-4186-b4e7-87f005a827dc

Files

Original bundle
Now showing 1 - 1 of 1
No Thumbnail Available
Name:
2016 Luso Galego Hélio.pdf
Size:
804.83 KB
Format:
Adobe Portable Document Format
Download
License bundle
Now showing 1 - 1 of 1
No Thumbnail Available
Name:
license.txt
Size:
1.75 KB
Format:
Item-specific license agreed upon to submission
Description:
Download

Collections

CIMO - Resumos em Proceedings Não Indexados à WoS/Scopus