Cycloaddition of methyl 2-(2,6-dichorophenyl)-2H-azirine-3-carboxylate to electron rich 2-azadienes

Detalhes bibliográficos
Autor(a) principal: Alves, M. José
Data de Publicação: 2003
Outros Autores: Durães, M. Miguel, Fortes, A. Gil
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: https://hdl.handle.net/1822/1845
Resumo: Tert-Butyldimethylsililoxy-2-aza-1,3-butadienes react with 2H-azirine 3 leading to Diels-Alder cycloadducts in moderate yields. The reactions are endo- and regio- selective with the azirine being added by its less hindered face. There is only one product in the case of 1b, 4b. There are two isomers (4 and 5) from 1a, 1c and 1d. A different result was obtained with the diene 1e. Diene 1e formed products 4e and 8. Some of compounds 4 and 5 have been hydrolysed leading to functionalized aziridines 7. Compound 8 gave aziridine 9.
id RCAP_53d61f5096375c6a852e74c50277c904
oai_identifier_str oai:repositorium.sdum.uminho.pt:1822/1845
network_acronym_str RCAP
network_name_str Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
repository_id_str 7160
spelling Cycloaddition of methyl 2-(2,6-dichorophenyl)-2H-azirine-3-carboxylate to electron rich 2-azadienes2-azadienes2H-azirinesDiels-alder reactionsScience & TechnologyTert-Butyldimethylsililoxy-2-aza-1,3-butadienes react with 2H-azirine 3 leading to Diels-Alder cycloadducts in moderate yields. The reactions are endo- and regio- selective with the azirine being added by its less hindered face. There is only one product in the case of 1b, 4b. There are two isomers (4 and 5) from 1a, 1c and 1d. A different result was obtained with the diene 1e. Diene 1e formed products 4e and 8. Some of compounds 4 and 5 have been hydrolysed leading to functionalized aziridines 7. Compound 8 gave aziridine 9.Fundação para a Ciência e Tecnologia - POCTI/32723/QUI/2000. FEDER.ElsevierUniversidade do MinhoAlves, M. JoséDurães, M. MiguelFortes, A. Gil20032003-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttps://hdl.handle.net/1822/1845engAlves, M. J., Durães, M. M., & Gil Fortes, A. (2003, June). Cycloaddition of methyl 2-(2,6-dichorophenyl)-2H-azirine-3-carboxylate to electron-rich 2-azadienes. Tetrahedron Letters. Elsevier BV. http://doi.org/10.1016/s0040-4039(03)01138-90040-403910.1016/S0040-4039(03)01138-9info: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:RCAAP2023-07-21T12:45:39Zoai:repositorium.sdum.uminho.pt:1822/1845Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T19:43:31.433347Repositório 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 Cycloaddition of methyl 2-(2,6-dichorophenyl)-2H-azirine-3-carboxylate to electron rich 2-azadienes
title Cycloaddition of methyl 2-(2,6-dichorophenyl)-2H-azirine-3-carboxylate to electron rich 2-azadienes
spellingShingle Cycloaddition of methyl 2-(2,6-dichorophenyl)-2H-azirine-3-carboxylate to electron rich 2-azadienes
Alves, M. José
2-azadienes
2H-azirines
Diels-alder reactions
Science & Technology
title_short Cycloaddition of methyl 2-(2,6-dichorophenyl)-2H-azirine-3-carboxylate to electron rich 2-azadienes
title_full Cycloaddition of methyl 2-(2,6-dichorophenyl)-2H-azirine-3-carboxylate to electron rich 2-azadienes
title_fullStr Cycloaddition of methyl 2-(2,6-dichorophenyl)-2H-azirine-3-carboxylate to electron rich 2-azadienes
title_full_unstemmed Cycloaddition of methyl 2-(2,6-dichorophenyl)-2H-azirine-3-carboxylate to electron rich 2-azadienes
title_sort Cycloaddition of methyl 2-(2,6-dichorophenyl)-2H-azirine-3-carboxylate to electron rich 2-azadienes
author Alves, M. José
author_facet Alves, M. José
Durães, M. Miguel
Fortes, A. Gil
author_role author
author2 Durães, M. Miguel
Fortes, A. Gil
author2_role author
author
dc.contributor.none.fl_str_mv Universidade do Minho
dc.contributor.author.fl_str_mv Alves, M. José
Durães, M. Miguel
Fortes, A. Gil
dc.subject.por.fl_str_mv 2-azadienes
2H-azirines
Diels-alder reactions
Science & Technology
topic 2-azadienes
2H-azirines
Diels-alder reactions
Science & Technology
description Tert-Butyldimethylsililoxy-2-aza-1,3-butadienes react with 2H-azirine 3 leading to Diels-Alder cycloadducts in moderate yields. The reactions are endo- and regio- selective with the azirine being added by its less hindered face. There is only one product in the case of 1b, 4b. There are two isomers (4 and 5) from 1a, 1c and 1d. A different result was obtained with the diene 1e. Diene 1e formed products 4e and 8. Some of compounds 4 and 5 have been hydrolysed leading to functionalized aziridines 7. Compound 8 gave aziridine 9.
publishDate 2003
dc.date.none.fl_str_mv 2003
2003-01-01T00:00:00Z
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 https://hdl.handle.net/1822/1845
url https://hdl.handle.net/1822/1845
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv Alves, M. J., Durães, M. M., & Gil Fortes, A. (2003, June). Cycloaddition of methyl 2-(2,6-dichorophenyl)-2H-azirine-3-carboxylate to electron-rich 2-azadienes. Tetrahedron Letters. Elsevier BV. http://doi.org/10.1016/s0040-4039(03)01138-9
0040-4039
10.1016/S0040-4039(03)01138-9
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
repository.mail.fl_str_mv
_version_ 1799132992177700864

Registros relacionados