DBU as a catalyst for the synthesis of amides via aminolysis of methyl esters
Autor(a) principal: | |
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Data de Publicação: | 2011 |
Outros Autores: | , , , , , |
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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Journal of the Brazilian Chemical Society (Online) |
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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 |
_version_ |
1750318172747071488 |