Microwave-assisted synthesis of 4,6-disubstituted isoindoline-1,3-diones by Diels-Alder reactions
Autor(a) principal: | |
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Data de Publicação: | 2023 |
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/10773/40419 |
Resumo: | The synthesis of 4,6-disubstituted isoindoline-1,3-diones through microwave-assisted Diels-Alder (DA) reactions is reported. Chromones bearing an α,β-unsaturated carbonyl system at C-3 were used as dienes and a scope of maleimides as dienophiles was investigated. The proposed mechanism involves a DA reaction of 3-benzoylvinylchromones with different maleimides, followed by chromanone ring opening and in situ oxidation. The observed aromatization of DA adducts was accomplished without employment of any oxidizing agent and can be explained by the presence of several acidic protons due to the electron-withdrawing groups (carbonyl groups), affording the 4,6-disubstituted isoindoline-1,3-diones in 15-59% yield. Among tested maleimides, N-phenylmaleimide revealed to be the most reactive dienophile, yielding the corresponding 2-phenylisoindoline-1,3-dione in 59% yield. |
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Microwave-assisted synthesis of 4,6-disubstituted isoindoline-1,3-diones by Diels-Alder reactions3-Substituted chromoneDiels-Alder reactionIsoindoline-1,3-dioneMicrowave chemistryMaleimideThe synthesis of 4,6-disubstituted isoindoline-1,3-diones through microwave-assisted Diels-Alder (DA) reactions is reported. Chromones bearing an α,β-unsaturated carbonyl system at C-3 were used as dienes and a scope of maleimides as dienophiles was investigated. The proposed mechanism involves a DA reaction of 3-benzoylvinylchromones with different maleimides, followed by chromanone ring opening and in situ oxidation. The observed aromatization of DA adducts was accomplished without employment of any oxidizing agent and can be explained by the presence of several acidic protons due to the electron-withdrawing groups (carbonyl groups), affording the 4,6-disubstituted isoindoline-1,3-diones in 15-59% yield. Among tested maleimides, N-phenylmaleimide revealed to be the most reactive dienophile, yielding the corresponding 2-phenylisoindoline-1,3-dione in 59% yield.Elsevier2024-01-31T11:45:43Z2023-03-01T00:00:00Z2023-03info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10773/40419eng0022-286010.1016/j.molstruc.2022.134608Nouali, FatihaSousa, Joana L. C.Albuquerque, Hélio M. T.Mendes, Ricardo F.Paz, Filipe A. AlmeidaSaher, LizaKibou, ZahiraChoukchou-Braham, NouredineTalhi, OualidSilva, Artur M. S.info: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:RCAAP2024-02-22T12:19:24Zoai:ria.ua.pt:10773/40419Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-20T03:10:30.312631Repositório 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 |
Microwave-assisted synthesis of 4,6-disubstituted isoindoline-1,3-diones by Diels-Alder reactions |
title |
Microwave-assisted synthesis of 4,6-disubstituted isoindoline-1,3-diones by Diels-Alder reactions |
spellingShingle |
Microwave-assisted synthesis of 4,6-disubstituted isoindoline-1,3-diones by Diels-Alder reactions Nouali, Fatiha 3-Substituted chromone Diels-Alder reaction Isoindoline-1,3-dione Microwave chemistry Maleimide |
title_short |
Microwave-assisted synthesis of 4,6-disubstituted isoindoline-1,3-diones by Diels-Alder reactions |
title_full |
Microwave-assisted synthesis of 4,6-disubstituted isoindoline-1,3-diones by Diels-Alder reactions |
title_fullStr |
Microwave-assisted synthesis of 4,6-disubstituted isoindoline-1,3-diones by Diels-Alder reactions |
title_full_unstemmed |
Microwave-assisted synthesis of 4,6-disubstituted isoindoline-1,3-diones by Diels-Alder reactions |
title_sort |
Microwave-assisted synthesis of 4,6-disubstituted isoindoline-1,3-diones by Diels-Alder reactions |
author |
Nouali, Fatiha |
author_facet |
Nouali, Fatiha Sousa, Joana L. C. Albuquerque, Hélio M. T. Mendes, Ricardo F. Paz, Filipe A. Almeida Saher, Liza Kibou, Zahira Choukchou-Braham, Nouredine Talhi, Oualid Silva, Artur M. S. |
author_role |
author |
author2 |
Sousa, Joana L. C. Albuquerque, Hélio M. T. Mendes, Ricardo F. Paz, Filipe A. Almeida Saher, Liza Kibou, Zahira Choukchou-Braham, Nouredine Talhi, Oualid Silva, Artur M. S. |
author2_role |
author author author author author author author author author |
dc.contributor.author.fl_str_mv |
Nouali, Fatiha Sousa, Joana L. C. Albuquerque, Hélio M. T. Mendes, Ricardo F. Paz, Filipe A. Almeida Saher, Liza Kibou, Zahira Choukchou-Braham, Nouredine Talhi, Oualid Silva, Artur M. S. |
dc.subject.por.fl_str_mv |
3-Substituted chromone Diels-Alder reaction Isoindoline-1,3-dione Microwave chemistry Maleimide |
topic |
3-Substituted chromone Diels-Alder reaction Isoindoline-1,3-dione Microwave chemistry Maleimide |
description |
The synthesis of 4,6-disubstituted isoindoline-1,3-diones through microwave-assisted Diels-Alder (DA) reactions is reported. Chromones bearing an α,β-unsaturated carbonyl system at C-3 were used as dienes and a scope of maleimides as dienophiles was investigated. The proposed mechanism involves a DA reaction of 3-benzoylvinylchromones with different maleimides, followed by chromanone ring opening and in situ oxidation. The observed aromatization of DA adducts was accomplished without employment of any oxidizing agent and can be explained by the presence of several acidic protons due to the electron-withdrawing groups (carbonyl groups), affording the 4,6-disubstituted isoindoline-1,3-diones in 15-59% yield. Among tested maleimides, N-phenylmaleimide revealed to be the most reactive dienophile, yielding the corresponding 2-phenylisoindoline-1,3-dione in 59% yield. |
publishDate |
2023 |
dc.date.none.fl_str_mv |
2023-03-01T00:00:00Z 2023-03 2024-01-31T11:45:43Z |
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/10773/40419 |
url |
http://hdl.handle.net/10773/40419 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
0022-2860 10.1016/j.molstruc.2022.134608 |
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 |
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 |
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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) |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
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