Palladium-catalysed reactions of 8-hydroxy- and 8-benzyloxy-5,7-diiodoquinoline under aminocarbonylation conditions

Detalhes bibliográficos
Autor(a) principal: Takács, Attila
Data de Publicação: 2011
Outros Autores: Szilágyi, Antal, Ács, Péter, Márk, László, Peixoto, Andreia F., Pereira, Mariette M., Kollár, László
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
DOI: 10.1016/j.tet.2011.02.003
Texto Completo: http://hdl.handle.net/10316/21203
https://doi.org/10.1016/j.tet.2011.02.003
Resumo: Various 5-carboxamido-7-iodo-8-benzyloxyquinolines were synthesised via selective aminocarbonylation of 5,7-diiodo-8-benzyloxyquinoline in the presence of ‘in situ’ generated palladium(0) catalysts. Under similar conditions (50 °C, 80 bar CO), 5,7-bis(N-tert-butyl-glyoxylamido)-8-hydroxyquinoline was obtained using tert-butylamine as N-nucleophile. The unprotected 5,7-diiodo-8-hydroxyquinoline underwent dehydroiodination resulting in 8-hydroxyquinoline as the major product.
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spelling Palladium-catalysed reactions of 8-hydroxy- and 8-benzyloxy-5,7-diiodoquinoline under aminocarbonylation conditionsIodo-aromatics8-HydroxyquinolineAminocarbonylationCarbon monoxidePalladiumVarious 5-carboxamido-7-iodo-8-benzyloxyquinolines were synthesised via selective aminocarbonylation of 5,7-diiodo-8-benzyloxyquinoline in the presence of ‘in situ’ generated palladium(0) catalysts. Under similar conditions (50 °C, 80 bar CO), 5,7-bis(N-tert-butyl-glyoxylamido)-8-hydroxyquinoline was obtained using tert-butylamine as N-nucleophile. The unprotected 5,7-diiodo-8-hydroxyquinoline underwent dehydroiodination resulting in 8-hydroxyquinoline as the major product.Elsevier2011-04info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttp://hdl.handle.net/10316/21203http://hdl.handle.net/10316/21203https://doi.org/10.1016/j.tet.2011.02.003engTAKÁCS, Attila [et al.] - Palladium-catalysed reactions of 8-hydroxy- and 8-benzyloxy-5,7-diiodoquinoline under aminocarbonylation conditions. "Tetrahedron". ISSN 0040-4020. 67:13 (2011) 2402-24060040-4020http://www.sciencedirect.com/science/journal/00404020Takács, AttilaSzilágyi, AntalÁcs, PéterMárk, LászlóPeixoto, Andreia F.Pereira, Mariette M.Kollár, Lászlóinfo: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:RCAAP2019-06-02T10:53:49Zoai:estudogeral.uc.pt:10316/21203Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T21:01:47.950671Repositório 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 Palladium-catalysed reactions of 8-hydroxy- and 8-benzyloxy-5,7-diiodoquinoline under aminocarbonylation conditions
title Palladium-catalysed reactions of 8-hydroxy- and 8-benzyloxy-5,7-diiodoquinoline under aminocarbonylation conditions
spellingShingle Palladium-catalysed reactions of 8-hydroxy- and 8-benzyloxy-5,7-diiodoquinoline under aminocarbonylation conditions
Palladium-catalysed reactions of 8-hydroxy- and 8-benzyloxy-5,7-diiodoquinoline under aminocarbonylation conditions
Takács, Attila
Iodo-aromatics
8-Hydroxyquinoline
Aminocarbonylation
Carbon monoxide
Palladium
Takács, Attila
Iodo-aromatics
8-Hydroxyquinoline
Aminocarbonylation
Carbon monoxide
Palladium
title_short Palladium-catalysed reactions of 8-hydroxy- and 8-benzyloxy-5,7-diiodoquinoline under aminocarbonylation conditions
title_full Palladium-catalysed reactions of 8-hydroxy- and 8-benzyloxy-5,7-diiodoquinoline under aminocarbonylation conditions
title_fullStr Palladium-catalysed reactions of 8-hydroxy- and 8-benzyloxy-5,7-diiodoquinoline under aminocarbonylation conditions
Palladium-catalysed reactions of 8-hydroxy- and 8-benzyloxy-5,7-diiodoquinoline under aminocarbonylation conditions
title_full_unstemmed Palladium-catalysed reactions of 8-hydroxy- and 8-benzyloxy-5,7-diiodoquinoline under aminocarbonylation conditions
Palladium-catalysed reactions of 8-hydroxy- and 8-benzyloxy-5,7-diiodoquinoline under aminocarbonylation conditions
title_sort Palladium-catalysed reactions of 8-hydroxy- and 8-benzyloxy-5,7-diiodoquinoline under aminocarbonylation conditions
author Takács, Attila
author_facet Takács, Attila
Takács, Attila
Szilágyi, Antal
Ács, Péter
Márk, László
Peixoto, Andreia F.
Pereira, Mariette M.
Kollár, László
Szilágyi, Antal
Ács, Péter
Márk, László
Peixoto, Andreia F.
Pereira, Mariette M.
Kollár, László
author_role author
author2 Szilágyi, Antal
Ács, Péter
Márk, László
Peixoto, Andreia F.
Pereira, Mariette M.
Kollár, László
author2_role author
author
author
author
author
author
dc.contributor.author.fl_str_mv Takács, Attila
Szilágyi, Antal
Ács, Péter
Márk, László
Peixoto, Andreia F.
Pereira, Mariette M.
Kollár, László
dc.subject.por.fl_str_mv Iodo-aromatics
8-Hydroxyquinoline
Aminocarbonylation
Carbon monoxide
Palladium
topic Iodo-aromatics
8-Hydroxyquinoline
Aminocarbonylation
Carbon monoxide
Palladium
description Various 5-carboxamido-7-iodo-8-benzyloxyquinolines were synthesised via selective aminocarbonylation of 5,7-diiodo-8-benzyloxyquinoline in the presence of ‘in situ’ generated palladium(0) catalysts. Under similar conditions (50 °C, 80 bar CO), 5,7-bis(N-tert-butyl-glyoxylamido)-8-hydroxyquinoline was obtained using tert-butylamine as N-nucleophile. The unprotected 5,7-diiodo-8-hydroxyquinoline underwent dehydroiodination resulting in 8-hydroxyquinoline as the major product.
publishDate 2011
dc.date.none.fl_str_mv 2011-04
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/10316/21203
http://hdl.handle.net/10316/21203
https://doi.org/10.1016/j.tet.2011.02.003
url http://hdl.handle.net/10316/21203
https://doi.org/10.1016/j.tet.2011.02.003
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv TAKÁCS, Attila [et al.] - Palladium-catalysed reactions of 8-hydroxy- and 8-benzyloxy-5,7-diiodoquinoline under aminocarbonylation conditions. "Tetrahedron". ISSN 0040-4020. 67:13 (2011) 2402-2406
0040-4020
http://www.sciencedirect.com/science/journal/00404020
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
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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dc.identifier.doi.none.fl_str_mv 10.1016/j.tet.2011.02.003

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