Synthesis and Ring Transformation of Oxygen and Nitrogen Spiro Bisheterocycles

Detalhes bibliográficos
Autor(a) principal: Talhi, Oualid
Data de Publicação: 2015
Outros Autores: Pinto, Diana C. G. A., Almeida Paz, Filipe A., Hamdi, Maamar, 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/10773/20280
Resumo: A facile and rapid access to bridgehead oxygen-and nitrogen-containing spiro bisheterocycles is reported. It involves a one-pot spiro-to-spiro ring transformation of the key spiro[chromanone-hydantoin] compounds into new substituted spiro [hydantoin-diazole], spiro [hydantoin-isoxazole], spiro [hydantoin-diazepine], spiro [hydantoinoxazepine], and spiro [hydantoin-benzodiazepine] upon reaction with appropriate bisnucleophilic agents. The hydantoin cycle is preserved during these chemical reactions affording the spiro bisheterocycles in optimal yields (42-71%). This relevant spiro-to-spiro ring transformation was confirmed by NMR and single-crystal X-ray diffraction studies.
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spelling Synthesis and Ring Transformation of Oxygen and Nitrogen Spiro Bisheterocyclesspiro bisheterocyclesoxygen and nitrogen heterocyclesbisnucleophilesNMRX-ray diffractionA facile and rapid access to bridgehead oxygen-and nitrogen-containing spiro bisheterocycles is reported. It involves a one-pot spiro-to-spiro ring transformation of the key spiro[chromanone-hydantoin] compounds into new substituted spiro [hydantoin-diazole], spiro [hydantoin-isoxazole], spiro [hydantoin-diazepine], spiro [hydantoinoxazepine], and spiro [hydantoin-benzodiazepine] upon reaction with appropriate bisnucleophilic agents. The hydantoin cycle is preserved during these chemical reactions affording the spiro bisheterocycles in optimal yields (42-71%). This relevant spiro-to-spiro ring transformation was confirmed by NMR and single-crystal X-ray diffraction studies.GEORG THIEME VERLAG KG2017-12-07T19:41:35Z2015-01-01T00:00:00Z2015info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10773/20280eng0936-521410.1055/s-0034-1379613Talhi, OualidPinto, Diana C. G. A.Almeida Paz, Filipe A.Hamdi, MaamarSilva, 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:RCAAP2024-02-22T11:39:44Zoai:ria.ua.pt:10773/20280Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-20T02:54:59.647737Repositório 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 Synthesis and Ring Transformation of Oxygen and Nitrogen Spiro Bisheterocycles
title Synthesis and Ring Transformation of Oxygen and Nitrogen Spiro Bisheterocycles
spellingShingle Synthesis and Ring Transformation of Oxygen and Nitrogen Spiro Bisheterocycles
Talhi, Oualid
spiro bisheterocycles
oxygen and nitrogen heterocycles
bisnucleophiles
NMR
X-ray diffraction
title_short Synthesis and Ring Transformation of Oxygen and Nitrogen Spiro Bisheterocycles
title_full Synthesis and Ring Transformation of Oxygen and Nitrogen Spiro Bisheterocycles
title_fullStr Synthesis and Ring Transformation of Oxygen and Nitrogen Spiro Bisheterocycles
title_full_unstemmed Synthesis and Ring Transformation of Oxygen and Nitrogen Spiro Bisheterocycles
title_sort Synthesis and Ring Transformation of Oxygen and Nitrogen Spiro Bisheterocycles
author Talhi, Oualid
author_facet Talhi, Oualid
Pinto, Diana C. G. A.
Almeida Paz, Filipe A.
Hamdi, Maamar
Silva, Artur M. S.
author_role author
author2 Pinto, Diana C. G. A.
Almeida Paz, Filipe A.
Hamdi, Maamar
Silva, Artur M. S.
author2_role author
author
author
author
dc.contributor.author.fl_str_mv Talhi, Oualid
Pinto, Diana C. G. A.
Almeida Paz, Filipe A.
Hamdi, Maamar
Silva, Artur M. S.
dc.subject.por.fl_str_mv spiro bisheterocycles
oxygen and nitrogen heterocycles
bisnucleophiles
NMR
X-ray diffraction
topic spiro bisheterocycles
oxygen and nitrogen heterocycles
bisnucleophiles
NMR
X-ray diffraction
description A facile and rapid access to bridgehead oxygen-and nitrogen-containing spiro bisheterocycles is reported. It involves a one-pot spiro-to-spiro ring transformation of the key spiro[chromanone-hydantoin] compounds into new substituted spiro [hydantoin-diazole], spiro [hydantoin-isoxazole], spiro [hydantoin-diazepine], spiro [hydantoinoxazepine], and spiro [hydantoin-benzodiazepine] upon reaction with appropriate bisnucleophilic agents. The hydantoin cycle is preserved during these chemical reactions affording the spiro bisheterocycles in optimal yields (42-71%). This relevant spiro-to-spiro ring transformation was confirmed by NMR and single-crystal X-ray diffraction studies.
publishDate 2015
dc.date.none.fl_str_mv 2015-01-01T00:00:00Z
2015
2017-12-07T19:41:35Z
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/10773/20280
url http://hdl.handle.net/10773/20280
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 0936-5214
10.1055/s-0034-1379613
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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