Reductive cleavage of N-substituted aromatic amides as tert-butyl acylcarbamates

Detalhes bibliográficos
Autor(a) principal: Ragnarsson, Ulf
Data de Publicação: 2002
Outros Autores: Grehn, Leif, Maia, Hernâni L. S., Monteiro, Luís S.
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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spelling 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
instname_str 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)
collection Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
repository.name.fl_str_mv Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
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