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

Detalhes bibliográficos
Autor(a) principal: Abdi, Yamina
Data de Publicação: 2015
Outros Autores: Boutemeur-Kheddis, Baya, Hamdi, Maamar, Talhi, Oualid, Paz, Filipe A. Almeida, Kirsch, Gilbert, Silva, Artur M. S.
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.
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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
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