A study of the sequential Michael addition-ring closure reaction of ethyl acetoacetate with chalcone: influence of quaternary ammonium cations as phase transfer catalysts

Detalhes bibliográficos
Autor(a) principal: Lopes,Regina C. V.
Data de Publicação: 2005
Outros Autores: Oliveira,Maria da Conceição F. de, Lemos,Telma L. G. de, Mattos,Marcos C. de
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Journal of the Brazilian Chemical Society (Online)
Texto Completo: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532005000600023
Resumo: The Michael addition of ethyl acetoacetate 1 to chalcone 2 under Solid/Liquid Phase Transfer Catalysis (SL-PTC), solvent free, afforded Michael adduct 3 and an annulated compound 4 in good yield. The cyclic compound 4 was obtained in the majority via an annulation process of the Michael adduct 3. The proportion of 4 in the ratio of 3/4 was dependant on the structure of the quaternary ammonium cation. The results were interpreted on the basis of the organophilicity and accessibility of the catalysts as well as by invoking a 6-membered ring transition state for the formation of 4 due to the chelation level with Q+.
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spelling A study of the sequential Michael addition-ring closure reaction of ethyl acetoacetate with chalcone: influence of quaternary ammonium cations as phase transfer catalystsPhase Transfer CatalysisannulationMichael reactionThe Michael addition of ethyl acetoacetate 1 to chalcone 2 under Solid/Liquid Phase Transfer Catalysis (SL-PTC), solvent free, afforded Michael adduct 3 and an annulated compound 4 in good yield. The cyclic compound 4 was obtained in the majority via an annulation process of the Michael adduct 3. The proportion of 4 in the ratio of 3/4 was dependant on the structure of the quaternary ammonium cation. The results were interpreted on the basis of the organophilicity and accessibility of the catalysts as well as by invoking a 6-membered ring transition state for the formation of 4 due to the chelation level with Q+.Sociedade Brasileira de Química2005-10-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532005000600023Journal of the Brazilian Chemical Society v.16 n.5 2005reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0103-50532005000600023info:eu-repo/semantics/openAccessLopes,Regina C. V.Oliveira,Maria da Conceição F. deLemos,Telma L. G. deMattos,Marcos C. deeng2005-11-09T00:00:00Zoai:scielo:S0103-50532005000600023Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2005-11-09T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv A study of the sequential Michael addition-ring closure reaction of ethyl acetoacetate with chalcone: influence of quaternary ammonium cations as phase transfer catalysts
title A study of the sequential Michael addition-ring closure reaction of ethyl acetoacetate with chalcone: influence of quaternary ammonium cations as phase transfer catalysts
spellingShingle A study of the sequential Michael addition-ring closure reaction of ethyl acetoacetate with chalcone: influence of quaternary ammonium cations as phase transfer catalysts
Lopes,Regina C. V.
Phase Transfer Catalysis
annulation
Michael reaction
title_short A study of the sequential Michael addition-ring closure reaction of ethyl acetoacetate with chalcone: influence of quaternary ammonium cations as phase transfer catalysts
title_full A study of the sequential Michael addition-ring closure reaction of ethyl acetoacetate with chalcone: influence of quaternary ammonium cations as phase transfer catalysts
title_fullStr A study of the sequential Michael addition-ring closure reaction of ethyl acetoacetate with chalcone: influence of quaternary ammonium cations as phase transfer catalysts
title_full_unstemmed A study of the sequential Michael addition-ring closure reaction of ethyl acetoacetate with chalcone: influence of quaternary ammonium cations as phase transfer catalysts
title_sort A study of the sequential Michael addition-ring closure reaction of ethyl acetoacetate with chalcone: influence of quaternary ammonium cations as phase transfer catalysts
author Lopes,Regina C. V.
author_facet Lopes,Regina C. V.
Oliveira,Maria da Conceição F. de
Lemos,Telma L. G. de
Mattos,Marcos C. de
author_role author
author2 Oliveira,Maria da Conceição F. de
Lemos,Telma L. G. de
Mattos,Marcos C. de
author2_role author
author
author
dc.contributor.author.fl_str_mv Lopes,Regina C. V.
Oliveira,Maria da Conceição F. de
Lemos,Telma L. G. de
Mattos,Marcos C. de
dc.subject.por.fl_str_mv Phase Transfer Catalysis
annulation
Michael reaction
topic Phase Transfer Catalysis
annulation
Michael reaction
description The Michael addition of ethyl acetoacetate 1 to chalcone 2 under Solid/Liquid Phase Transfer Catalysis (SL-PTC), solvent free, afforded Michael adduct 3 and an annulated compound 4 in good yield. The cyclic compound 4 was obtained in the majority via an annulation process of the Michael adduct 3. The proportion of 4 in the ratio of 3/4 was dependant on the structure of the quaternary ammonium cation. The results were interpreted on the basis of the organophilicity and accessibility of the catalysts as well as by invoking a 6-membered ring transition state for the formation of 4 due to the chelation level with Q+.
publishDate 2005
dc.date.none.fl_str_mv 2005-10-01
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532005000600023
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532005000600023
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.1590/S0103-50532005000600023
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv text/html
dc.publisher.none.fl_str_mv Sociedade Brasileira de Química
publisher.none.fl_str_mv Sociedade Brasileira de Química
dc.source.none.fl_str_mv Journal of the Brazilian Chemical Society v.16 n.5 2005
reponame:Journal of the Brazilian Chemical Society (Online)
instname:Sociedade Brasileira de Química (SBQ)
instacron:SBQ
instname_str Sociedade Brasileira de Química (SBQ)
instacron_str SBQ
institution SBQ
reponame_str Journal of the Brazilian Chemical Society (Online)
collection Journal of the Brazilian Chemical Society (Online)
repository.name.fl_str_mv Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)
repository.mail.fl_str_mv ||office@jbcs.sbq.org.br
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