Reductive cleavage of N-substituted aromatic amides as tert-butyl acylcarbamates
Autor(a) principal: | |
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Data de Publicação: | 2002 |
Outros Autores: | , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
Texto Completo: | https://hdl.handle.net/1822/2182 |
Resumo: | Synthetic and spectroscopic details related to a set of heteroaromatic N-benzyl carboxamides and especially the corresponding tert-butyl acylcarbamates are reported. These compounds were required to study the postulated effect of various heterocycles (pyridine and pyrazine with and without condensed benzene rings) on the cleavage of acyl-N bonds by reduction. All compounds were initially characterized by cyclic voltammetry which indicated various degrees of facilitated reduction, reflecting a direct influence of the heterocyclic component. Selected acylcarbamates were studied with respect to acyl-N bond cleavage by mild reducing agents and selectively deacylated by activated aluminium and sodium borohydride. Conversion to acylcarbamates followed by reduction might therefore be a mild, efficient two-step procedure to effect cleavage of amides, allowing isolation of carbamates and with sodium borohydride also the corresponding alcohols. |
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Reductive cleavage of N-substituted aromatic amides as tert-butyl acylcarbamatesScience & TechnologySynthetic and spectroscopic details related to a set of heteroaromatic N-benzyl carboxamides and especially the corresponding tert-butyl acylcarbamates are reported. These compounds were required to study the postulated effect of various heterocycles (pyridine and pyrazine with and without condensed benzene rings) on the cleavage of acyl-N bonds by reduction. All compounds were initially characterized by cyclic voltammetry which indicated various degrees of facilitated reduction, reflecting a direct influence of the heterocyclic component. Selected acylcarbamates were studied with respect to acyl-N bond cleavage by mild reducing agents and selectively deacylated by activated aluminium and sodium borohydride. Conversion to acylcarbamates followed by reduction might therefore be a mild, efficient two-step procedure to effect cleavage of amides, allowing isolation of carbamates and with sodium borohydride also the corresponding alcohols.Fundação para a Ciência e Tecnologia. NFR and Magnus Bergvalls Stiftelse. RSC. TFR.Royal Society of ChemistryUniversidade do MinhoRagnarsson, UlfGrehn, LeifMaia, Hernâni L. S.Monteiro, Luís S.20022002-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttps://hdl.handle.net/1822/2182eng“Journal of the chemical society. Perkin transactions”. 1 (2002) 97-101.1472-778110.1039/b107330ninfo:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2023-07-21T12:53:11Zoai:repositorium.sdum.uminho.pt:1822/2182Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T19:52:30.614203Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse |
dc.title.none.fl_str_mv |
Reductive cleavage of N-substituted aromatic amides as tert-butyl acylcarbamates |
title |
Reductive cleavage of N-substituted aromatic amides as tert-butyl acylcarbamates |
spellingShingle |
Reductive cleavage of N-substituted aromatic amides as tert-butyl acylcarbamates Ragnarsson, Ulf Science & Technology |
title_short |
Reductive cleavage of N-substituted aromatic amides as tert-butyl acylcarbamates |
title_full |
Reductive cleavage of N-substituted aromatic amides as tert-butyl acylcarbamates |
title_fullStr |
Reductive cleavage of N-substituted aromatic amides as tert-butyl acylcarbamates |
title_full_unstemmed |
Reductive cleavage of N-substituted aromatic amides as tert-butyl acylcarbamates |
title_sort |
Reductive cleavage of N-substituted aromatic amides as tert-butyl acylcarbamates |
author |
Ragnarsson, Ulf |
author_facet |
Ragnarsson, Ulf Grehn, Leif Maia, Hernâni L. S. Monteiro, Luís S. |
author_role |
author |
author2 |
Grehn, Leif Maia, Hernâni L. S. Monteiro, Luís S. |
author2_role |
author author author |
dc.contributor.none.fl_str_mv |
Universidade do Minho |
dc.contributor.author.fl_str_mv |
Ragnarsson, Ulf Grehn, Leif Maia, Hernâni L. S. Monteiro, Luís S. |
dc.subject.por.fl_str_mv |
Science & Technology |
topic |
Science & Technology |
description |
Synthetic and spectroscopic details related to a set of heteroaromatic N-benzyl carboxamides and especially the corresponding tert-butyl acylcarbamates are reported. These compounds were required to study the postulated effect of various heterocycles (pyridine and pyrazine with and without condensed benzene rings) on the cleavage of acyl-N bonds by reduction. All compounds were initially characterized by cyclic voltammetry which indicated various degrees of facilitated reduction, reflecting a direct influence of the heterocyclic component. Selected acylcarbamates were studied with respect to acyl-N bond cleavage by mild reducing agents and selectively deacylated by activated aluminium and sodium borohydride. Conversion to acylcarbamates followed by reduction might therefore be a mild, efficient two-step procedure to effect cleavage of amides, allowing isolation of carbamates and with sodium borohydride also the corresponding alcohols. |
publishDate |
2002 |
dc.date.none.fl_str_mv |
2002 2002-01-01T00:00:00Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
https://hdl.handle.net/1822/2182 |
url |
https://hdl.handle.net/1822/2182 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
“Journal of the chemical society. Perkin transactions”. 1 (2002) 97-101. 1472-7781 10.1039/b107330n |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
application/pdf |
dc.publisher.none.fl_str_mv |
Royal Society of Chemistry |
publisher.none.fl_str_mv |
Royal Society of Chemistry |
dc.source.none.fl_str_mv |
reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação instacron:RCAAP |
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Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
instacron_str |
RCAAP |
institution |
RCAAP |
reponame_str |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
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1799133117940760576 |