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

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

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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Main Authors: 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.
Format: Digital revista
Language:English
Published: Sociedade Brasileira de Química 2011
Online Access:http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532011001100023
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spelling oai:scielo:S0103-505320110011000232011-11-04DBU as a catalyst for the synthesis of amides via aminolysis of methyl estersLima,Evanoel Crizanto deSouza,Carolina C. deSoares,Renato de O.Vaz,Boniek GontijoEberlin,Marcos N.Dias,Ayres G.Costa,Paulo R. R. DBU catalysis aminolysis esters amides ESI-MS 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.info:eu-repo/semantics/openAccessSociedade Brasileira de QuímicaJournal of the Brazilian Chemical Society v.22 n.11 20112011-11-01info:eu-repo/semantics/articletext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532011001100023en10.1590/S0103-50532011001100023
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country Brasil
countrycode BR
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databasecode rev-scielo-br
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region America del Sur
libraryname SciELO
language English
format Digital
author 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.
spellingShingle 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.
DBU as a catalyst for the synthesis of amides via aminolysis of methyl esters
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_sort Lima,Evanoel Crizanto de
title DBU as a catalyst for the synthesis of amides via aminolysis of methyl esters
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
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.
publisher Sociedade Brasileira de Química
publishDate 2011
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532011001100023
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