DBU as a catalyst for the synthesis of amides via aminolysis of methyl esters

Detalhes bibliográficos
Autor(a) principal: Lima,Evanoel Crizanto de
Data de Publicação: 2011
Outros Autores: Souza,Carolina C. de, Soares,Renato de O., Vaz,Boniek Gontijo, Eberlin,Marcos N., Dias,Ayres G., Costa,Paulo R. R.
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=S0103-50532011001100023
Resumo: Methyl benzoate and methyl p-chlorophenyl acetate react with neat benzylamine and pyrrolidine to form the corresponding amides. These reactions are faster in the presence of 20 mol% of DBU providing slight better yields. When a diester derived from L-aspartic acid was used as substrate, the reaction with benzylamine and pyrrolidine in the presence of DBU was chemoselective and led to the corresponding amides in good yields. Reaction of aspartic acid monomethyl ester with these amines led to amides having a free carboxy group (at C1). Less nucleophilic and less basic aniline failed to form the expected products in both absence and presence of DBU. By monitoring the course of reaction by ESI-MS, key charged intermediates formed by the reactions of methyl benzoate and methyl p-chlorophenyl acetate with benzylamine were intercepted and further characterized by ESI-MS/MS.
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spelling DBU as a catalyst for the synthesis of amides via aminolysis of methyl estersDBUcatalysisaminolysisestersamidesESI-MSMethyl benzoate and methyl p-chlorophenyl acetate react with neat benzylamine and pyrrolidine to form the corresponding amides. These reactions are faster in the presence of 20 mol% of DBU providing slight better yields. When a diester derived from L-aspartic acid was used as substrate, the reaction with benzylamine and pyrrolidine in the presence of DBU was chemoselective and led to the corresponding amides in good yields. Reaction of aspartic acid monomethyl ester with these amines led to amides having a free carboxy group (at C1). Less nucleophilic and less basic aniline failed to form the expected products in both absence and presence of DBU. By monitoring the course of reaction by ESI-MS, key charged intermediates formed by the reactions of methyl benzoate and methyl p-chlorophenyl acetate with benzylamine were intercepted and further characterized by ESI-MS/MS.Sociedade Brasileira de Química2011-11-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532011001100023Journal of the Brazilian Chemical Society v.22 n.11 2011reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0103-50532011001100023info:eu-repo/semantics/openAccessLima,Evanoel Crizanto deSouza,Carolina C. deSoares,Renato de O.Vaz,Boniek GontijoEberlin,Marcos N.Dias,Ayres G.Costa,Paulo R. R.eng2011-11-04T00:00:00Zoai:scielo:S0103-50532011001100023Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2011-11-04T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv DBU as a catalyst for the synthesis of amides via aminolysis of methyl esters
title DBU as a catalyst for the synthesis of amides via aminolysis of methyl esters
spellingShingle DBU as a catalyst for the synthesis of amides via aminolysis of methyl esters
Lima,Evanoel Crizanto de
DBU
catalysis
aminolysis
esters
amides
ESI-MS
title_short DBU as a catalyst for the synthesis of amides via aminolysis of methyl esters
title_full DBU as a catalyst for the synthesis of amides via aminolysis of methyl esters
title_fullStr DBU as a catalyst for the synthesis of amides via aminolysis of methyl esters
title_full_unstemmed DBU as a catalyst for the synthesis of amides via aminolysis of methyl esters
title_sort DBU as a catalyst for the synthesis of amides via aminolysis of methyl esters
author Lima,Evanoel Crizanto de
author_facet Lima,Evanoel Crizanto de
Souza,Carolina C. de
Soares,Renato de O.
Vaz,Boniek Gontijo
Eberlin,Marcos N.
Dias,Ayres G.
Costa,Paulo R. R.
author_role author
author2 Souza,Carolina C. de
Soares,Renato de O.
Vaz,Boniek Gontijo
Eberlin,Marcos N.
Dias,Ayres G.
Costa,Paulo R. R.
author2_role author
author
author
author
author
author
dc.contributor.author.fl_str_mv Lima,Evanoel Crizanto de
Souza,Carolina C. de
Soares,Renato de O.
Vaz,Boniek Gontijo
Eberlin,Marcos N.
Dias,Ayres G.
Costa,Paulo R. R.
dc.subject.por.fl_str_mv DBU
catalysis
aminolysis
esters
amides
ESI-MS
topic DBU
catalysis
aminolysis
esters
amides
ESI-MS
description Methyl benzoate and methyl p-chlorophenyl acetate react with neat benzylamine and pyrrolidine to form the corresponding amides. These reactions are faster in the presence of 20 mol% of DBU providing slight better yields. When a diester derived from L-aspartic acid was used as substrate, the reaction with benzylamine and pyrrolidine in the presence of DBU was chemoselective and led to the corresponding amides in good yields. Reaction of aspartic acid monomethyl ester with these amines led to amides having a free carboxy group (at C1). Less nucleophilic and less basic aniline failed to form the expected products in both absence and presence of DBU. By monitoring the course of reaction by ESI-MS, key charged intermediates formed by the reactions of methyl benzoate and methyl p-chlorophenyl acetate with benzylamine were intercepted and further characterized by ESI-MS/MS.
publishDate 2011
dc.date.none.fl_str_mv 2011-11-01
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=S0103-50532011001100023
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532011001100023
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.1590/S0103-50532011001100023
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.22 n.11 2011
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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