An efficient protocol for accessing β-amino dicarbonyl compounds through aza-Michael reaction

Detalhes bibliográficos
Autor(a) principal: Meskini,Ihssan
Data de Publicação: 2010
Outros Autores: Toupet,Loïc, Daoudi,Maria, Kerbal,Abdelali, Bennani,Brahim, Dixneuf,Pierre H., Chohan,Zahid H., Leite,Ana Cristina Lima, Hadda,Taibi Ben
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=S0103-50532010000600025
Resumo: β-Amino dicarbonyl compounds comprise a class of useful ligands on the coordination chemistry. In view of their importance, an efficient and facile method for the synthesis of β-amino dicarbonyl compounds has been developed, exploring the aza-Michael addition reactions in an aqueous medium. It was possible to achieve good to excellent yields, along with regioselectivity, the substituted diethyl 2-(phenylmethyl)malonates that were easily isolated without any chromatographic purification. The correct configuration of two of these β-amino dicarbonyl compounds were confirmed by X-ray crystallography. A complementary mechanism of this aza-Michael protocol is proposed to explain the results obtained.
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spelling An efficient protocol for accessing β-amino dicarbonyl compounds through aza-Michael reactionpolydentate ligandsβ-amino dicarbonyl compoundsMichael additionaqueous mediumβ-Amino dicarbonyl compounds comprise a class of useful ligands on the coordination chemistry. In view of their importance, an efficient and facile method for the synthesis of β-amino dicarbonyl compounds has been developed, exploring the aza-Michael addition reactions in an aqueous medium. It was possible to achieve good to excellent yields, along with regioselectivity, the substituted diethyl 2-(phenylmethyl)malonates that were easily isolated without any chromatographic purification. The correct configuration of two of these β-amino dicarbonyl compounds were confirmed by X-ray crystallography. A complementary mechanism of this aza-Michael protocol is proposed to explain the results obtained.Sociedade Brasileira de Química2010-01-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532010000600025Journal of the Brazilian Chemical Society v.21 n.6 2010reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0103-50532010000600025info:eu-repo/semantics/openAccessMeskini,IhssanToupet,LoïcDaoudi,MariaKerbal,AbdelaliBennani,BrahimDixneuf,Pierre H.Chohan,Zahid H.Leite,Ana Cristina LimaHadda,Taibi Beneng2010-07-19T00:00:00Zoai:scielo:S0103-50532010000600025Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2010-07-19T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv An efficient protocol for accessing β-amino dicarbonyl compounds through aza-Michael reaction
title An efficient protocol for accessing β-amino dicarbonyl compounds through aza-Michael reaction
spellingShingle An efficient protocol for accessing β-amino dicarbonyl compounds through aza-Michael reaction
Meskini,Ihssan
polydentate ligands
β-amino dicarbonyl compounds
Michael addition
aqueous medium
title_short An efficient protocol for accessing β-amino dicarbonyl compounds through aza-Michael reaction
title_full An efficient protocol for accessing β-amino dicarbonyl compounds through aza-Michael reaction
title_fullStr An efficient protocol for accessing β-amino dicarbonyl compounds through aza-Michael reaction
title_full_unstemmed An efficient protocol for accessing β-amino dicarbonyl compounds through aza-Michael reaction
title_sort An efficient protocol for accessing β-amino dicarbonyl compounds through aza-Michael reaction
author Meskini,Ihssan
author_facet Meskini,Ihssan
Toupet,Loïc
Daoudi,Maria
Kerbal,Abdelali
Bennani,Brahim
Dixneuf,Pierre H.
Chohan,Zahid H.
Leite,Ana Cristina Lima
Hadda,Taibi Ben
author_role author
author2 Toupet,Loïc
Daoudi,Maria
Kerbal,Abdelali
Bennani,Brahim
Dixneuf,Pierre H.
Chohan,Zahid H.
Leite,Ana Cristina Lima
Hadda,Taibi Ben
author2_role author
author
author
author
author
author
author
author
dc.contributor.author.fl_str_mv Meskini,Ihssan
Toupet,Loïc
Daoudi,Maria
Kerbal,Abdelali
Bennani,Brahim
Dixneuf,Pierre H.
Chohan,Zahid H.
Leite,Ana Cristina Lima
Hadda,Taibi Ben
dc.subject.por.fl_str_mv polydentate ligands
β-amino dicarbonyl compounds
Michael addition
aqueous medium
topic polydentate ligands
β-amino dicarbonyl compounds
Michael addition
aqueous medium
description β-Amino dicarbonyl compounds comprise a class of useful ligands on the coordination chemistry. In view of their importance, an efficient and facile method for the synthesis of β-amino dicarbonyl compounds has been developed, exploring the aza-Michael addition reactions in an aqueous medium. It was possible to achieve good to excellent yields, along with regioselectivity, the substituted diethyl 2-(phenylmethyl)malonates that were easily isolated without any chromatographic purification. The correct configuration of two of these β-amino dicarbonyl compounds were confirmed by X-ray crystallography. A complementary mechanism of this aza-Michael protocol is proposed to explain the results obtained.
publishDate 2010
dc.date.none.fl_str_mv 2010-01-01
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=S0103-50532010000600025
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532010000600025
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.1590/S0103-50532010000600025
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.21 n.6 2010
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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