First intramolecular Diels-Alder reactions using chromone derivatives: Synthesis of chromeno[3,4-: B] xanthones and 2-(benzo [c] chromenyl)chromones
Autor(a) principal: | |
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Data de Publicação: | 2018 |
Outros Autores: | , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
Texto Completo: | http://hdl.handle.net/10198/17908 |
Resumo: | A series of novel (E)-2-(2-propargyloxystyryl)chromones and (E,E)-2-[4-(2-propargyloxyphenyl)buta-1,3-dien-1-yl]chromones were designed and synthesized via aldol condensation of 2-methylchromones with 2-propargyloxy(benzaldehyde and cinnamaldehyde), respectively. Both chromone derivatives were used as substrates in microwave-assisted intramolecular Diels-Alder reactions, affording chromeno[3,4-b]xanthones and 2-(benzo[c]chromenyl)chromones. This is the first report involving chromone derivatives in intramolecular Diels-Alder reactions for the synthesis of new oxygen heterocycles, namely xanthone- and flavone-type compounds. |
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First intramolecular Diels-Alder reactions using chromone derivatives: Synthesis of chromeno[3,4-: B] xanthones and 2-(benzo [c] chromenyl)chromonesA series of novel (E)-2-(2-propargyloxystyryl)chromones and (E,E)-2-[4-(2-propargyloxyphenyl)buta-1,3-dien-1-yl]chromones were designed and synthesized via aldol condensation of 2-methylchromones with 2-propargyloxy(benzaldehyde and cinnamaldehyde), respectively. Both chromone derivatives were used as substrates in microwave-assisted intramolecular Diels-Alder reactions, affording chromeno[3,4-b]xanthones and 2-(benzo[c]chromenyl)chromones. This is the first report involving chromone derivatives in intramolecular Diels-Alder reactions for the synthesis of new oxygen heterocycles, namely xanthone- and flavone-type compounds.Thanks are due to the University of Aveiro and FCT/MEC for the financial support of the QOPNA research unit (FCTUID/QUI/ 00062/2013) through national funds and, where applicable, co-financed by the FEDER, within the PT2020 Partnership Agreement, and to the Portuguese NMR Network, as well as to the Instituto Politécnico de Bragança. H. M. T. A. is grateful to FCT for his PhD grant (SFRH/BD/86277/2012).Biblioteca Digital do IPBAlbuquerque, HélioSantos, Clementina M.M.Cavaleiro, JoséSilva, Artur2018-01-19T10:00:00Z20182018-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10198/17908engAlbuquerque, Hélio M.T.; Santos, Clementina M.M.; Cavaleiro, José A.S.; Silva, Artur M.S. (2018). First intramolecular Diels-Alder reactions using chromone derivatives: Synthesis of chromeno[3,4-: B] xanthones and 2-(benzo [c] chromenyl)chromones. New Journal of Chemistry. ISSN 11440546. 42:6, p. 4251-42601144-054610.1039/c7nj05185ainfo: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:RCAAP2023-11-21T10:41:03Zoai:bibliotecadigital.ipb.pt:10198/17908Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T23:07:49.682738Repositório 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 |
First intramolecular Diels-Alder reactions using chromone derivatives: Synthesis of chromeno[3,4-: B] xanthones and 2-(benzo [c] chromenyl)chromones |
title |
First intramolecular Diels-Alder reactions using chromone derivatives: Synthesis of chromeno[3,4-: B] xanthones and 2-(benzo [c] chromenyl)chromones |
spellingShingle |
First intramolecular Diels-Alder reactions using chromone derivatives: Synthesis of chromeno[3,4-: B] xanthones and 2-(benzo [c] chromenyl)chromones Albuquerque, Hélio |
title_short |
First intramolecular Diels-Alder reactions using chromone derivatives: Synthesis of chromeno[3,4-: B] xanthones and 2-(benzo [c] chromenyl)chromones |
title_full |
First intramolecular Diels-Alder reactions using chromone derivatives: Synthesis of chromeno[3,4-: B] xanthones and 2-(benzo [c] chromenyl)chromones |
title_fullStr |
First intramolecular Diels-Alder reactions using chromone derivatives: Synthesis of chromeno[3,4-: B] xanthones and 2-(benzo [c] chromenyl)chromones |
title_full_unstemmed |
First intramolecular Diels-Alder reactions using chromone derivatives: Synthesis of chromeno[3,4-: B] xanthones and 2-(benzo [c] chromenyl)chromones |
title_sort |
First intramolecular Diels-Alder reactions using chromone derivatives: Synthesis of chromeno[3,4-: B] xanthones and 2-(benzo [c] chromenyl)chromones |
author |
Albuquerque, Hélio |
author_facet |
Albuquerque, Hélio Santos, Clementina M.M. Cavaleiro, José Silva, Artur |
author_role |
author |
author2 |
Santos, Clementina M.M. Cavaleiro, José Silva, Artur |
author2_role |
author author author |
dc.contributor.none.fl_str_mv |
Biblioteca Digital do IPB |
dc.contributor.author.fl_str_mv |
Albuquerque, Hélio Santos, Clementina M.M. Cavaleiro, José Silva, Artur |
description |
A series of novel (E)-2-(2-propargyloxystyryl)chromones and (E,E)-2-[4-(2-propargyloxyphenyl)buta-1,3-dien-1-yl]chromones were designed and synthesized via aldol condensation of 2-methylchromones with 2-propargyloxy(benzaldehyde and cinnamaldehyde), respectively. Both chromone derivatives were used as substrates in microwave-assisted intramolecular Diels-Alder reactions, affording chromeno[3,4-b]xanthones and 2-(benzo[c]chromenyl)chromones. This is the first report involving chromone derivatives in intramolecular Diels-Alder reactions for the synthesis of new oxygen heterocycles, namely xanthone- and flavone-type compounds. |
publishDate |
2018 |
dc.date.none.fl_str_mv |
2018-01-19T10:00:00Z 2018 2018-01-01T00:00:00Z |
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/10198/17908 |
url |
http://hdl.handle.net/10198/17908 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
Albuquerque, Hélio M.T.; Santos, Clementina M.M.; Cavaleiro, José A.S.; Silva, Artur M.S. (2018). First intramolecular Diels-Alder reactions using chromone derivatives: Synthesis of chromeno[3,4-: B] xanthones and 2-(benzo [c] chromenyl)chromones. New Journal of Chemistry. ISSN 11440546. 42:6, p. 4251-4260 1144-0546 10.1039/c7nj05185a |
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.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 |
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Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
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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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1799135335509131264 |