Sequential catalytic carbonylation reactions for sustainable synthesis of biologically relevant entities

Detalhes bibliográficos
Autor(a) principal: Damas, Liliana Reis
Data de Publicação: 2020
Outros Autores: Rodrigues, Fábio M.S., Gonzalez, Andreia C.S., Carrilho, Rui Miguel Barroso, Piñeiro Gomez, Marta, Pereira, Maria Miguéns
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10316/95597
https://doi.org/10.1016/j.jorganchem.2020.121417
Resumo: The sustainable synthesis of highly functionalised formylcarboxamide compounds with biological relevance is reported through a sequential aminocarbonylation/hydroformylation approach. The optimisation of palladium-catalysed aminocarbonylation of iodoaromatic substrates, using allylamine as nucleophile was first performed, with molybdenum hexacarbonyl as alternative CO source versus gaseous carbon monoxide. The combination of microwave irradiation with molybdenum hexacarbonyl allowed to selectively prepare a set of N-heterocyclic-based allylcarboxamides. Subsequent rhodium-catalysed hydroformylation of the allylcarboxamide intermediates led to the preparation of new pyridine, pyrazoline and chalcone derivatives containing both carboxamide and formyl moieties.
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spelling Sequential catalytic carbonylation reactions for sustainable synthesis of biologically relevant entitiesSequential reactionsAminocarbonylationHydroformylationMicrowave synthesisN-heterocyclesChalconesThe sustainable synthesis of highly functionalised formylcarboxamide compounds with biological relevance is reported through a sequential aminocarbonylation/hydroformylation approach. The optimisation of palladium-catalysed aminocarbonylation of iodoaromatic substrates, using allylamine as nucleophile was first performed, with molybdenum hexacarbonyl as alternative CO source versus gaseous carbon monoxide. The combination of microwave irradiation with molybdenum hexacarbonyl allowed to selectively prepare a set of N-heterocyclic-based allylcarboxamides. Subsequent rhodium-catalysed hydroformylation of the allylcarboxamide intermediates led to the preparation of new pyridine, pyrazoline and chalcone derivatives containing both carboxamide and formyl moieties.Elsevier2020info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttp://hdl.handle.net/10316/95597http://hdl.handle.net/10316/95597https://doi.org/10.1016/j.jorganchem.2020.121417eng0022328Xhttps://www.sciencedirect.com/science/article/pii/S0022328X20303193#!Damas, Liliana ReisRodrigues, Fábio M.S.Gonzalez, Andreia C.S.Carrilho, Rui Miguel BarrosoPiñeiro Gomez, MartaPereira, Maria Miguénsinfo: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:RCAAP2022-05-25T06:05:36Zoai:estudogeral.uc.pt:10316/95597Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T21:12:07.292984Repositório 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 Sequential catalytic carbonylation reactions for sustainable synthesis of biologically relevant entities
title Sequential catalytic carbonylation reactions for sustainable synthesis of biologically relevant entities
spellingShingle Sequential catalytic carbonylation reactions for sustainable synthesis of biologically relevant entities
Damas, Liliana Reis
Sequential reactions
Aminocarbonylation
Hydroformylation
Microwave synthesis
N-heterocyclesChalcones
title_short Sequential catalytic carbonylation reactions for sustainable synthesis of biologically relevant entities
title_full Sequential catalytic carbonylation reactions for sustainable synthesis of biologically relevant entities
title_fullStr Sequential catalytic carbonylation reactions for sustainable synthesis of biologically relevant entities
title_full_unstemmed Sequential catalytic carbonylation reactions for sustainable synthesis of biologically relevant entities
title_sort Sequential catalytic carbonylation reactions for sustainable synthesis of biologically relevant entities
author Damas, Liliana Reis
author_facet Damas, Liliana Reis
Rodrigues, Fábio M.S.
Gonzalez, Andreia C.S.
Carrilho, Rui Miguel Barroso
Piñeiro Gomez, Marta
Pereira, Maria Miguéns
author_role author
author2 Rodrigues, Fábio M.S.
Gonzalez, Andreia C.S.
Carrilho, Rui Miguel Barroso
Piñeiro Gomez, Marta
Pereira, Maria Miguéns
author2_role author
author
author
author
author
dc.contributor.author.fl_str_mv Damas, Liliana Reis
Rodrigues, Fábio M.S.
Gonzalez, Andreia C.S.
Carrilho, Rui Miguel Barroso
Piñeiro Gomez, Marta
Pereira, Maria Miguéns
dc.subject.por.fl_str_mv Sequential reactions
Aminocarbonylation
Hydroformylation
Microwave synthesis
N-heterocyclesChalcones
topic Sequential reactions
Aminocarbonylation
Hydroformylation
Microwave synthesis
N-heterocyclesChalcones
description The sustainable synthesis of highly functionalised formylcarboxamide compounds with biological relevance is reported through a sequential aminocarbonylation/hydroformylation approach. The optimisation of palladium-catalysed aminocarbonylation of iodoaromatic substrates, using allylamine as nucleophile was first performed, with molybdenum hexacarbonyl as alternative CO source versus gaseous carbon monoxide. The combination of microwave irradiation with molybdenum hexacarbonyl allowed to selectively prepare a set of N-heterocyclic-based allylcarboxamides. Subsequent rhodium-catalysed hydroformylation of the allylcarboxamide intermediates led to the preparation of new pyridine, pyrazoline and chalcone derivatives containing both carboxamide and formyl moieties.
publishDate 2020
dc.date.none.fl_str_mv 2020
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/10316/95597
http://hdl.handle.net/10316/95597
https://doi.org/10.1016/j.jorganchem.2020.121417
url http://hdl.handle.net/10316/95597
https://doi.org/10.1016/j.jorganchem.2020.121417
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 0022328X
https://www.sciencedirect.com/science/article/pii/S0022328X20303193#!
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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