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)
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
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
title_full_unstemmed 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
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
repository.mail.fl_str_mv
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