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Conjugate additions of carbon nucleophiles to chromones substituted with extended π-systems at C-2

2017Conference object Open access
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dc.contributor.authorAlbuquerque, Hélio
dc.contributor.authorSantos, Clementina M.M.
dc.contributor.authorBalanay, Mannix P.
dc.contributor.authorCavaleiro, José
dc.contributor.authorSilva, Artur
dc.date.accessioned2020-07-20T13:23:51Z
dc.date.available2020-07-20T13:23:51Z
dc.date.issued2017
dc.description.abstractThe conjugate addition of carbon nucleophiles to electron deficient alkenes is an important method for carbon-carbon bond formation [1]. Generally, 1,4-conjugate addition reactions are more developed than its analogous 1,6- or 1,8-additions, mainly due to the presence of several electrophilic sites in extended conjugated systems as well as the inherent difficulties in controlling the regioselectivity (1,4- vs. 1,6- vs. 1,8-addition) [1]. In this work, we provide new experimental and computational insights about the reactivity of the 3,2:α,β:γ,δ-triunsaturated system of the 2-[(1E,3E)-4-arylbuta-1,3-dien-1-yl]-4H-chromen-4-ones 1 in conjugate addition reactions with carbon nucleophiles (Figure 1). The 1,6-conjugate addition of nitromethane to chromones 1 afforded the corresponding β-(nitromethyl)chromones 2 as major products. (E)-5′-(Nitromethyl)-3′-styryl-[1,1′-biphenyl]-2-ols 3 and 3′-aryl-2′-nitro-5′- (nitromethyl)spiro[chromane-2,1′-cyclohexan]-4-ones 4 were also isolated as minor products, which result from tandem reactions [2]. The nucleophile scope (malononitrile, acetylacetone, diethyl malonate and ethyl cyanoacetate) of this reaction was also assessed and gave, in all cases, the expected 1,6-addition products 5 as major products. Computational calculations showed that the reaction is probably kinetically driven towards 1,6-addition. The further functionalization of some adducts allowed the preparation of new nitrogen-containing heterocyclic compounds, such as pyrazole derivative 6 and styrylpyrrolidines 7 [2].pt_PT
dc.description.sponsorshipThanks are due to the University of Aveiro and Fundação para a Ciência e a Tecnologia (FCT) / Ministério da Educação e Ciência (MEC) for the financial support of the QOPNA research unit (FCTUID/QUI/00062/2013) through national funds and, where applicable, cofinanced by Fundo Europeu de Desenvolvimento Regional (FEDER) within the PT2020 Partnership Agreement, and to the Portuguese NMR Network as well as the Polytechnic Institute of Bragança. H. M. T. A. is grateful to FCT for his PhD grant (SFRH/BD/86277/2012).pt_PT
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.citationAlbuquerque, Hélio; Santos, Clementina M.M.; Balanay, Mannix P.; Cavaleiro, José; Silva, Artur (2017). Conjugate additions of carbon nucleophiles to chromones substituted with extended π-systems at C-2. In XXIII Encontro Galelo Portugués de Química. Ferrol. ISBN 978-84-697-7356-7pt_PT
dc.identifier.isbn978-84-697-7356-7
dc.identifier.urihttp://hdl.handle.net/10198/22490
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.rights.urihttp://creativecommons.org/licenses/by-nc/4.0/pt_PT
dc.titleConjugate additions of carbon nucleophiles to chromones substituted with extended π-systems at C-2pt_PT
dc.typeconference object
dspace.entity.typePublication
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/5876/UID%2FQUI%2F00062%2F2013/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/SFRH/SFRH%2FBD%2F86277%2F2012/PT
oaire.citation.conferencePlaceFerrol, Espanhapt_PT
oaire.citation.startPage128pt_PT
oaire.citation.titleXXIII Encontro Galelo Portugués de Químicapt_PT
oaire.fundingStream5876
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.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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