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.author | Albuquerque, Hélio | |
dc.contributor.author | Santos, Clementina M.M. | |
dc.contributor.author | Balanay, Mannix P. | |
dc.contributor.author | Cavaleiro, José | |
dc.contributor.author | Silva, Artur | |
dc.date.accessioned | 2018-01-31T10:00:00Z | |
dc.date.accessioned | 2018-01-31T15:40:21Z | |
dc.date.available | 2018-01-31T10:00:00Z | |
dc.date.available | 2018-01-31T15:40:21Z | |
dc.date.issued | 2017 | |
dc.description.abstract | KGaA, 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.sponsorship | Thanks 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.version | info:eu-repo/semantics/publishedVersion | en_EN |
dc.identifier.citation | Albuquerque, 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. 5293-5305 | en_EN |
dc.identifier.doi | 10.1002/ejoc.201700944 | en_EN |
dc.identifier.issn | 1434-193X | |
dc.identifier.uri | http://hdl.handle.net/10198/15347 | |
dc.language.iso | eng | |
dc.peerreviewed | yes | en_EN |
dc.subject | Conjugate addition | en_EN |
dc.subject | Density functional calculations | en_EN |
dc.subject | Nitrogen heterocycles | en_EN |
dc.subject | Oxygen heterocycles | en_EN |
dc.title | 1,6-Conjugate Additions of Carbon Nucleophiles to 2-[(1E,3E)-4-Arylbuta-1,3-dien-1-yl]-4H-chromen-4-ones | en_EN |
dc.type | journal article | |
dspace.entity.type | Publication | |
oaire.awardURI | info:eu-repo/grantAgreement/FCT/5876/UID%2FQUI%2F00062%2F2013/PT | |
oaire.awardURI | info:eu-repo/grantAgreement/FCT/SFRH/SFRH%2FBD%2F86277%2F2012/PT | |
oaire.fundingStream | 5876 | |
oaire.fundingStream | SFRH | |
person.familyName | Santos | |
person.givenName | Clementina M.M. | |
person.identifier.ciencia-id | 9018-DB9C-C590 | |
person.identifier.orcid | 0000-0003-4380-7990 | |
person.identifier.scopus-author-id | 7201458663 | |
project.funder.identifier | http://doi.org/10.13039/501100001871 | |
project.funder.identifier | http://doi.org/10.13039/501100001871 | |
project.funder.name | Fundação para a Ciência e a Tecnologia | |
project.funder.name | Fundação para a Ciência e a Tecnologia | |
rcaap.rights | openAccess | en_EN |
rcaap.type | article | en_EN |
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