A novel and efficient route for the syntheses of hydroxylated 2,3-diarylxanthones

Detalhes bibliográficos
Autor(a) principal: Santos, Clementina M.M.
Data de Publicação: 2007
Outros Autores: Silva, Artur, Cavaleiro, José
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10198/3240
Resumo: A novel, efficient and general route for the synthesis of hy-droxylated 2,3-diarylxanthones is described. 3-Bromo-2-styrylchromones, the key intermediate of this synthesis, is obtained by a Baker-Venkataraman rearrangement of appropriate 2’-cinnamoyloxyacetophenones, followed by a one-pot reaction with phenyltrimethylammonium tribromide. The Heck reaction of these bromochromones with substituted styrenes gives methoxylated 2,3-diarylxanthones. The cleavage of the methyl groups with BBr3 gives the desired hydroxylated 2,3-diarylxanthones.
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spelling A novel and efficient route for the syntheses of hydroxylated 2,3-diarylxanthonesHydroxylated diarylxanthones3-bromo-2-styrylchromonesHeck reactionPhenyltrimethylammonium tribromideDemethylationA novel, efficient and general route for the synthesis of hy-droxylated 2,3-diarylxanthones is described. 3-Bromo-2-styrylchromones, the key intermediate of this synthesis, is obtained by a Baker-Venkataraman rearrangement of appropriate 2’-cinnamoyloxyacetophenones, followed by a one-pot reaction with phenyltrimethylammonium tribromide. The Heck reaction of these bromochromones with substituted styrenes gives methoxylated 2,3-diarylxanthones. The cleavage of the methyl groups with BBr3 gives the desired hydroxylated 2,3-diarylxanthones.Thieme VerlagBiblioteca Digital do IPBSantos, Clementina M.M.Silva, ArturCavaleiro, José2011-02-02T16:14:15Z20072007-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10198/3240engSantos, Clementina; Silva, Artur; Cavaleiro, José (2007). A novel and efficient route for the syntheses of hydroxylated 2,3-diarylxanthones. Synlett. 20, p. 3113-311610.1055/s-2007-990900info: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:RCAAP2023-11-21T10:08:21Zoai:bibliotecadigital.ipb.pt:10198/3240Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T22:56:08.567295Repositório 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 novel and efficient route for the syntheses of hydroxylated 2,3-diarylxanthones
title A novel and efficient route for the syntheses of hydroxylated 2,3-diarylxanthones
spellingShingle A novel and efficient route for the syntheses of hydroxylated 2,3-diarylxanthones
Santos, Clementina M.M.
Hydroxylated diarylxanthones
3-bromo-2-styrylchromones
Heck reaction
Phenyltrimethylammonium tribromide
Demethylation
title_short A novel and efficient route for the syntheses of hydroxylated 2,3-diarylxanthones
title_full A novel and efficient route for the syntheses of hydroxylated 2,3-diarylxanthones
title_fullStr A novel and efficient route for the syntheses of hydroxylated 2,3-diarylxanthones
title_full_unstemmed A novel and efficient route for the syntheses of hydroxylated 2,3-diarylxanthones
title_sort A novel and efficient route for the syntheses of hydroxylated 2,3-diarylxanthones
author Santos, Clementina M.M.
author_facet Santos, Clementina M.M.
Silva, Artur
Cavaleiro, José
author_role author
author2 Silva, Artur
Cavaleiro, José
author2_role author
author
dc.contributor.none.fl_str_mv Biblioteca Digital do IPB
dc.contributor.author.fl_str_mv Santos, Clementina M.M.
Silva, Artur
Cavaleiro, José
dc.subject.por.fl_str_mv Hydroxylated diarylxanthones
3-bromo-2-styrylchromones
Heck reaction
Phenyltrimethylammonium tribromide
Demethylation
topic Hydroxylated diarylxanthones
3-bromo-2-styrylchromones
Heck reaction
Phenyltrimethylammonium tribromide
Demethylation
description A novel, efficient and general route for the synthesis of hy-droxylated 2,3-diarylxanthones is described. 3-Bromo-2-styrylchromones, the key intermediate of this synthesis, is obtained by a Baker-Venkataraman rearrangement of appropriate 2’-cinnamoyloxyacetophenones, followed by a one-pot reaction with phenyltrimethylammonium tribromide. The Heck reaction of these bromochromones with substituted styrenes gives methoxylated 2,3-diarylxanthones. The cleavage of the methyl groups with BBr3 gives the desired hydroxylated 2,3-diarylxanthones.
publishDate 2007
dc.date.none.fl_str_mv 2007
2007-01-01T00:00:00Z
2011-02-02T16:14:15Z
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/10198/3240
url http://hdl.handle.net/10198/3240
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv Santos, Clementina; Silva, Artur; Cavaleiro, José (2007). A novel and efficient route for the syntheses of hydroxylated 2,3-diarylxanthones. Synlett. 20, p. 3113-3116
10.1055/s-2007-990900
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 Thieme Verlag
publisher.none.fl_str_mv Thieme Verlag
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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