Synthesis of 1,3,8,8a-tetrahydro-3,8-epoxy[1,2-b]isoquinolines and their reactions with oxygen nucleophiles

Detalhes bibliográficos
Autor(a) principal: Alves, M. José
Data de Publicação: 2005
Outros Autores: Fortes, A. Gil, Azóia, Nuno G.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/1822/3414
Resumo: Cycloadditions of 2H-azirines to isobenzofurans is described. The endo and exo products were obtained and were reacted with oxygen nucleophiles. Tetrahydroquinolines or benzofuranols were obtained, usually in excellent yields. Cycloaddition of the less electrophilic azirine (14) was performed at room temperature in the presence of ZnCl2. The cycloadduct was hydrolysed in the reaction conditions, but dehydration to give back the original cycloadduct was obtained in the presence of 4Å molecular sieves. The structure assigned in the literature to the product of hydrolysis of the cycloadduct 10 was rectified.
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spelling Synthesis of 1,3,8,8a-tetrahydro-3,8-epoxy[1,2-b]isoquinolines and their reactions with oxygen nucleophilesScience & TechnologyCycloadditions of 2H-azirines to isobenzofurans is described. The endo and exo products were obtained and were reacted with oxygen nucleophiles. Tetrahydroquinolines or benzofuranols were obtained, usually in excellent yields. Cycloaddition of the less electrophilic azirine (14) was performed at room temperature in the presence of ZnCl2. The cycloadduct was hydrolysed in the reaction conditions, but dehydration to give back the original cycloadduct was obtained in the presence of 4Å molecular sieves. The structure assigned in the literature to the product of hydrolysis of the cycloadduct 10 was rectified.Fundação para a Ciência e Tecnologia. FEDER - POCTI/QUI/32723/2000.ElsevierUniversidade do MinhoAlves, M. JoséFortes, A. GilAzóia, Nuno G.20052005-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/1822/3414eng"Heterocycles". ISSN 0385-5414. 65:6 (2005) 1329-1345.0385-541410.3987/COM-05-10365info: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:RCAAP2023-07-21T12:32:57Zoai:repositorium.sdum.uminho.pt:1822/3414Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T19:28:23.555072Repositório 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 of 1,3,8,8a-tetrahydro-3,8-epoxy[1,2-b]isoquinolines and their reactions with oxygen nucleophiles
title Synthesis of 1,3,8,8a-tetrahydro-3,8-epoxy[1,2-b]isoquinolines and their reactions with oxygen nucleophiles
spellingShingle Synthesis of 1,3,8,8a-tetrahydro-3,8-epoxy[1,2-b]isoquinolines and their reactions with oxygen nucleophiles
Alves, M. José
Science & Technology
title_short Synthesis of 1,3,8,8a-tetrahydro-3,8-epoxy[1,2-b]isoquinolines and their reactions with oxygen nucleophiles
title_full Synthesis of 1,3,8,8a-tetrahydro-3,8-epoxy[1,2-b]isoquinolines and their reactions with oxygen nucleophiles
title_fullStr Synthesis of 1,3,8,8a-tetrahydro-3,8-epoxy[1,2-b]isoquinolines and their reactions with oxygen nucleophiles
title_full_unstemmed Synthesis of 1,3,8,8a-tetrahydro-3,8-epoxy[1,2-b]isoquinolines and their reactions with oxygen nucleophiles
title_sort Synthesis of 1,3,8,8a-tetrahydro-3,8-epoxy[1,2-b]isoquinolines and their reactions with oxygen nucleophiles
author Alves, M. José
author_facet Alves, M. José
Fortes, A. Gil
Azóia, Nuno G.
author_role author
author2 Fortes, A. Gil
Azóia, Nuno G.
author2_role author
author
dc.contributor.none.fl_str_mv Universidade do Minho
dc.contributor.author.fl_str_mv Alves, M. José
Fortes, A. Gil
Azóia, Nuno G.
dc.subject.por.fl_str_mv Science & Technology
topic Science & Technology
description Cycloadditions of 2H-azirines to isobenzofurans is described. The endo and exo products were obtained and were reacted with oxygen nucleophiles. Tetrahydroquinolines or benzofuranols were obtained, usually in excellent yields. Cycloaddition of the less electrophilic azirine (14) was performed at room temperature in the presence of ZnCl2. The cycloadduct was hydrolysed in the reaction conditions, but dehydration to give back the original cycloadduct was obtained in the presence of 4Å molecular sieves. The structure assigned in the literature to the product of hydrolysis of the cycloadduct 10 was rectified.
publishDate 2005
dc.date.none.fl_str_mv 2005
2005-01-01T00:00:00Z
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/1822/3414
url http://hdl.handle.net/1822/3414
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv "Heterocycles". ISSN 0385-5414. 65:6 (2005) 1329-1345.
0385-5414
10.3987/COM-05-10365
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
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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