A One-Pot Diastereoselective Synthesis of 2-[Aryl(hydroxy)methyl]-6-methyl-2H-furo[3,2-c]pyran-3,4-diones: Crystallographic Evidence for the Furanone Ring Closure
Autor(a) principal: | |
---|---|
Data de Publicação: | 2015 |
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/10773/20649 |
Resumo: | Novel furopyran-3,4-dione-fused heterocycles have been obtained by a one-pot reaction of -brominated dehydroacetic acid and benzaldehydes under organobase conditions. The prepared 2-[aryl(hydroxy)methyl]-6-methyl-2H-furo[3,2-c]pyran-3,4-diones were fully characterized by 2D NMR spectroscopy and supported by single-crystal X-ray analysis to unequivocally prove the furan-3-one five-membered ring-closure mechanism instead of the dihydroflavanon-3-ol six-membered cyclization which has recently been proposed in the literature. |
id |
RCAP_ae15e1cd7ee8322eada57972670ad79d |
---|---|
oai_identifier_str |
oai:ria.ua.pt:10773/20649 |
network_acronym_str |
RCAP |
network_name_str |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
repository_id_str |
7160 |
spelling |
A One-Pot Diastereoselective Synthesis of 2-[Aryl(hydroxy)methyl]-6-methyl-2H-furo[3,2-c]pyran-3,4-diones: Crystallographic Evidence for the Furanone Ring ClosureSTEREOSELECTIVE-SYNTHESISMULTICOMPONENT APPROACHDERIVATIVES SYNTHESISBIOLOGICAL-ACTIVITYDEHYDROACETIC ACIDPENICILLIUM-SPAMINESCYCLIZATIONFLAVANONESFLAVONOIDSNovel furopyran-3,4-dione-fused heterocycles have been obtained by a one-pot reaction of -brominated dehydroacetic acid and benzaldehydes under organobase conditions. The prepared 2-[aryl(hydroxy)methyl]-6-methyl-2H-furo[3,2-c]pyran-3,4-diones were fully characterized by 2D NMR spectroscopy and supported by single-crystal X-ray analysis to unequivocally prove the furan-3-one five-membered ring-closure mechanism instead of the dihydroflavanon-3-ol six-membered cyclization which has recently been proposed in the literature.GEORG THIEME VERLAG KG2017-12-07T19:54:38Z2015-01-01T00:00:00Z2015info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10773/20649eng0936-521410.1055/s-0034-1380214Abdi, YaminaBoutemeur-Kheddis, BayaHamdi, MaamarTalhi, OualidPaz, Filipe A. AlmeidaKirsch, GilbertSilva, 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:RCAAP2024-02-22T11:40:37Zoai:ria.ua.pt:10773/20649Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-20T02:55:19.083665Repositório 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 |
A One-Pot Diastereoselective Synthesis of 2-[Aryl(hydroxy)methyl]-6-methyl-2H-furo[3,2-c]pyran-3,4-diones: Crystallographic Evidence for the Furanone Ring Closure |
title |
A One-Pot Diastereoselective Synthesis of 2-[Aryl(hydroxy)methyl]-6-methyl-2H-furo[3,2-c]pyran-3,4-diones: Crystallographic Evidence for the Furanone Ring Closure |
spellingShingle |
A One-Pot Diastereoselective Synthesis of 2-[Aryl(hydroxy)methyl]-6-methyl-2H-furo[3,2-c]pyran-3,4-diones: Crystallographic Evidence for the Furanone Ring Closure Abdi, Yamina STEREOSELECTIVE-SYNTHESIS MULTICOMPONENT APPROACH DERIVATIVES SYNTHESIS BIOLOGICAL-ACTIVITY DEHYDROACETIC ACID PENICILLIUM-SP AMINES CYCLIZATION FLAVANONES FLAVONOIDS |
title_short |
A One-Pot Diastereoselective Synthesis of 2-[Aryl(hydroxy)methyl]-6-methyl-2H-furo[3,2-c]pyran-3,4-diones: Crystallographic Evidence for the Furanone Ring Closure |
title_full |
A One-Pot Diastereoselective Synthesis of 2-[Aryl(hydroxy)methyl]-6-methyl-2H-furo[3,2-c]pyran-3,4-diones: Crystallographic Evidence for the Furanone Ring Closure |
title_fullStr |
A One-Pot Diastereoselective Synthesis of 2-[Aryl(hydroxy)methyl]-6-methyl-2H-furo[3,2-c]pyran-3,4-diones: Crystallographic Evidence for the Furanone Ring Closure |
title_full_unstemmed |
A One-Pot Diastereoselective Synthesis of 2-[Aryl(hydroxy)methyl]-6-methyl-2H-furo[3,2-c]pyran-3,4-diones: Crystallographic Evidence for the Furanone Ring Closure |
title_sort |
A One-Pot Diastereoselective Synthesis of 2-[Aryl(hydroxy)methyl]-6-methyl-2H-furo[3,2-c]pyran-3,4-diones: Crystallographic Evidence for the Furanone Ring Closure |
author |
Abdi, Yamina |
author_facet |
Abdi, Yamina Boutemeur-Kheddis, Baya Hamdi, Maamar Talhi, Oualid Paz, Filipe A. Almeida Kirsch, Gilbert Silva, Artur M. S. |
author_role |
author |
author2 |
Boutemeur-Kheddis, Baya Hamdi, Maamar Talhi, Oualid Paz, Filipe A. Almeida Kirsch, Gilbert Silva, Artur M. S. |
author2_role |
author author author author author author |
dc.contributor.author.fl_str_mv |
Abdi, Yamina Boutemeur-Kheddis, Baya Hamdi, Maamar Talhi, Oualid Paz, Filipe A. Almeida Kirsch, Gilbert Silva, Artur M. S. |
dc.subject.por.fl_str_mv |
STEREOSELECTIVE-SYNTHESIS MULTICOMPONENT APPROACH DERIVATIVES SYNTHESIS BIOLOGICAL-ACTIVITY DEHYDROACETIC ACID PENICILLIUM-SP AMINES CYCLIZATION FLAVANONES FLAVONOIDS |
topic |
STEREOSELECTIVE-SYNTHESIS MULTICOMPONENT APPROACH DERIVATIVES SYNTHESIS BIOLOGICAL-ACTIVITY DEHYDROACETIC ACID PENICILLIUM-SP AMINES CYCLIZATION FLAVANONES FLAVONOIDS |
description |
Novel furopyran-3,4-dione-fused heterocycles have been obtained by a one-pot reaction of -brominated dehydroacetic acid and benzaldehydes under organobase conditions. The prepared 2-[aryl(hydroxy)methyl]-6-methyl-2H-furo[3,2-c]pyran-3,4-diones were fully characterized by 2D NMR spectroscopy and supported by single-crystal X-ray analysis to unequivocally prove the furan-3-one five-membered ring-closure mechanism instead of the dihydroflavanon-3-ol six-membered cyclization which has recently been proposed in the literature. |
publishDate |
2015 |
dc.date.none.fl_str_mv |
2015-01-01T00:00:00Z 2015 2017-12-07T19:54:38Z |
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/10773/20649 |
url |
http://hdl.handle.net/10773/20649 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
0936-5214 10.1055/s-0034-1380214 |
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 |
GEORG THIEME VERLAG KG |
publisher.none.fl_str_mv |
GEORG THIEME VERLAG KG |
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 |
|
_version_ |
1799137606707970048 |