Repository logo
 
Publication

1,6-Conjugate Additions of Carbon Nucleophiles to 2-[(1E,3E)-4-Arylbuta-1,3-dien-1-yl]-4H-chromen-4-ones

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.accessioned2018-01-31T10:00:00Z
dc.date.accessioned2018-01-31T15:40:21Z
dc.date.available2018-01-31T10:00:00Z
dc.date.available2018-01-31T15:40:21Z
dc.date.issued2017
dc.description.abstractKGaA, Weinheim The 1,6-conjugate addition of nitromethane to 2-[(1E,3E)-4-arylbuta-1,3-dien-1-yl]-4H-chromen-4-ones was accomplished and led mainly to the corresponding β-(nitromethyl)chromones. (E)-5′-(Nitromethyl)-3′-styryl-[1,1′-biphenyl] -2-ol and 3′-aryl-2′-nitro-5′-(nitromethyl)spiro[chromane-2,1′-cyclohexan]-4-one derivatives were also isolated as minor products from tandem processes, which result from the addition of a second molecule of nitromethane. The nucleophile scope was investigated with malononitrile, acetylacetone, ethyl cyanoacetate, and diethyl malonate, which gave the expected 1,6-addition products; in the last case, it was also possible to isolate a minor product formed through a 1,8-/1,6-addition sequence. Computational calculations provided a rationale for the experimental reactivity of carbon nucleophiles with 2-[(1E,3E)-4-arylbuta-1,3-dien-1-yl] -4H-chromen-4-ones. The further functionalization of some adducts allowed the preparation of new nitrogen-containing heterocyclic compounds, such as new styrylpyrrolidines and new pyrazole and bis(pyrazole) derivatives.en_EN
dc.description.sponsorshipThanks are due to the University of Aveiro and Fundação para a Ciência e a Tecnologia (FCT)/Ministerio de Educación y Ciencia (MEC) for the financial support of the QOPNA research unit (FCT UID/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 Instituto Politécnico de Bragança. H. M. T. A. is grateful to Fundação para a Ciência e a Tecnologia (FCT) for his PhD grant (SFRH/BD/86277/ 2012).
dc.description.versioninfo:eu-repo/semantics/publishedVersionen_EN
dc.identifier.citationAlbuquerque, Hélio M.T.; Santos, Clementina M.M.; Balanay, Mannix P.; Cavaleiro, José A.S.; Silva, Artur M.S. (2017). 1,6-Conjugate Additions of Carbon Nucleophiles to 2-[(1E,3E)-4-Arylbuta-1,3-dien-1-yl]-4H-chromen-4-ones. European Journal of Organic Chemistry. ISSN 1434-193X. 2017, p. 5293-5305en_EN
dc.identifier.doi10.1002/ejoc.201700944en_EN
dc.identifier.issn1434-193X
dc.identifier.urihttp://hdl.handle.net/10198/15347
dc.language.isoeng
dc.peerreviewedyesen_EN
dc.subjectConjugate additionen_EN
dc.subjectDensity functional calculationsen_EN
dc.subjectNitrogen heterocyclesen_EN
dc.subjectOxygen heterocyclesen_EN
dc.title1,6-Conjugate Additions of Carbon Nucleophiles to 2-[(1E,3E)-4-Arylbuta-1,3-dien-1-yl]-4H-chromen-4-onesen_EN
dc.typejournal article
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.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.rightsopenAccessen_EN
rcaap.typearticleen_EN
relation.isAuthorOfPublication64f662b6-775d-4ea0-bfd7-f527af0ac1a0
relation.isAuthorOfPublication.latestForDiscovery64f662b6-775d-4ea0-bfd7-f527af0ac1a0
relation.isProjectOfPublicationa955d531-2af9-40df-baaf-a064d8a697e9
relation.isProjectOfPublicationb1a3433a-76f8-4132-b2c2-8f3aeeb902e2
relation.isProjectOfPublication.latestForDiscoverya955d531-2af9-40df-baaf-a064d8a697e9

Files

Original bundle
Now showing 1 - 1 of 1
No Thumbnail Available
Name:
11.pdf
Size:
1.82 MB
Format:
Adobe Portable Document Format
License bundle
Now showing 1 - 1 of 1
No Thumbnail Available
Name:
license.txt
Size:
1.75 KB
Format:
Plain Text
Description: