Enhancing reductive cleavage of aromatic carboxamides

Detalhes bibliográficos
Autor(a) principal: Ragnarsson, Ulf
Data de Publicação: 2001
Outros Autores: Grehn, Leif, Maia, Hernâni Lopes Silva, Monteiro, Luís S.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/1822/72910
Resumo: [GRAPHICS] A set of aromatic and especially heteroaromatic N-benzyl carboxamides, derived from naphthalene, pyridine, pyrazine, and quinoline, and the corresponding tert-butyl acylcarbamates have been synthesized and studied by cyclic voltammetry with respect to facilitated reduction. The latter undergo regiospecific cleavage of their C(O)-N bonds under very mild reductive conditions with formation of Boc-protected (benzyl)amine in most cases in nearly quantitative yields, Examples of preparative cleavage by controlled potential electrolysis, activated aluminum, and NaBH4 are given.
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spelling Enhancing reductive cleavage of aromatic carboxamidesScience & Technology[GRAPHICS] A set of aromatic and especially heteroaromatic N-benzyl carboxamides, derived from naphthalene, pyridine, pyrazine, and quinoline, and the corresponding tert-butyl acylcarbamates have been synthesized and studied by cyclic voltammetry with respect to facilitated reduction. The latter undergo regiospecific cleavage of their C(O)-N bonds under very mild reductive conditions with formation of Boc-protected (benzyl)amine in most cases in nearly quantitative yields, Examples of preparative cleavage by controlled potential electrolysis, activated aluminum, and NaBH4 are given.American Chemical SocietyUniversidade do MinhoRagnarsson, UlfGrehn, LeifMaia, Hernâni Lopes SilvaMonteiro, Luís S.20012001-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/1822/72910eng1523-706010.1021/ol010072ahttps://doi.org/10.1021/ol010072ainfo: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:RCAAP2023-07-21T12:51:28Zoai:repositorium.sdum.uminho.pt:1822/72910Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T19:50:23.015318Repositório 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 Enhancing reductive cleavage of aromatic carboxamides
title Enhancing reductive cleavage of aromatic carboxamides
spellingShingle Enhancing reductive cleavage of aromatic carboxamides
Ragnarsson, Ulf
Science & Technology
title_short Enhancing reductive cleavage of aromatic carboxamides
title_full Enhancing reductive cleavage of aromatic carboxamides
title_fullStr Enhancing reductive cleavage of aromatic carboxamides
title_full_unstemmed Enhancing reductive cleavage of aromatic carboxamides
title_sort Enhancing reductive cleavage of aromatic carboxamides
author Ragnarsson, Ulf
author_facet Ragnarsson, Ulf
Grehn, Leif
Maia, Hernâni Lopes Silva
Monteiro, Luís S.
author_role author
author2 Grehn, Leif
Maia, Hernâni Lopes Silva
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 Lopes Silva
Monteiro, Luís S.
dc.subject.por.fl_str_mv Science & Technology
topic Science & Technology
description [GRAPHICS] A set of aromatic and especially heteroaromatic N-benzyl carboxamides, derived from naphthalene, pyridine, pyrazine, and quinoline, and the corresponding tert-butyl acylcarbamates have been synthesized and studied by cyclic voltammetry with respect to facilitated reduction. The latter undergo regiospecific cleavage of their C(O)-N bonds under very mild reductive conditions with formation of Boc-protected (benzyl)amine in most cases in nearly quantitative yields, Examples of preparative cleavage by controlled potential electrolysis, activated aluminum, and NaBH4 are given.
publishDate 2001
dc.date.none.fl_str_mv 2001
2001-01-01T00:00:00Z
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 http://hdl.handle.net/1822/72910
url http://hdl.handle.net/1822/72910
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 1523-7060
10.1021/ol010072a
https://doi.org/10.1021/ol010072a
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 American Chemical Society
publisher.none.fl_str_mv American Chemical Society
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
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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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