Publicação
Diels-alder cycloaddition of 2-azadienes to methyl 2-(2,6-dichlorophenyl)-2H-azirine-3-carboxylate in the synthesis of methyl 4-oxo-1,3-diazabicyclo[4.1.0]heptane-6-carboxylates
| Resumo: | A number of fused 4-oxo-1,3-diazabicyclo[4.1.0]heptane-6-carboxylates, a new type of compound, have been obtained by Diels-Alder cycloaddition between nucleophilic 2-azadienes and an electrophilic 2H-azirine. The reactions are completely endo- and regioselective, the azirine being added by its less hindered face to the diene. There are two isomers 7 and 8 formed from dienes 1 due either to isomerization of the cycloadducts 7 and 8 or by isomerization of the C=N bond of the diene during the reaction. The isomer 10 is formed from diene 2e, and a single diastereoisomer structure 4a-i is formed from dienes 11. Some pyrimidones 8a,7c/8c, 7e, 10, 11d have been hydrolyzed leading to functionalised aziridines 12, 13 and 15. |
|---|---|
| Autores principais: | Alves, M. José |
| Outros Autores: | Durães, M. Miguel; Fortes, A. Gil |
| Assunto: | 2-azadienes 2H-azirines Diels-alder cycloaddition |
| Ano: | 2004 |
| País: | Portugal |
| Tipo de documento: | artigo |
| Tipo de acesso: | acesso aberto |
| Instituição associada: | Universidade do Minho |
| Idioma: | inglês |
| Origem: | RepositóriUM - Universidade do Minho |
| _version_ | 1866877929038807040 |
|---|---|
| author | Alves, M. José |
| author2 | Durães, M. Miguel Fortes, A. Gil |
| author2_role | author author |
| author_facet | Alves, M. José Durães, M. Miguel Fortes, A. Gil |
| author_role | author |
| contributor_name_str_mv | Universidade do Minho |
| country_str | PT |
| creators_json_txt | [{\"Person.name\":\"Alves, M. José\"},{\"Person.name\":\"Durães, M. Miguel\"},{\"Person.name\":\"Fortes, A. Gil\"}] |
| datacite.contributors.contributor.contributorName.fl_str_mv | Universidade do Minho |
| datacite.creators.creator.creatorName.fl_str_mv | Alves, M. José Durães, M. Miguel Fortes, A. Gil |
| datacite.date.Accepted.fl_str_mv | 2004-01-01T00:00:00Z |
| datacite.date.available.fl_str_mv | 2005-05-30T12:53:42Z |
| datacite.date.embargoed.fl_str_mv | 2005-05-30T12:53:42Z |
| datacite.rights.fl_str_mv | http://purl.org/coar/access_right/c_abf2 |
| datacite.subjects.subject.fl_str_mv | 2-azadienes 2H-azirines Diels-alder cycloaddition |
| datacite.titles.title.fl_str_mv | Diels-alder cycloaddition of 2-azadienes to methyl 2-(2,6-dichlorophenyl)-2H-azirine-3-carboxylate in the synthesis of methyl 4-oxo-1,3-diazabicyclo[4.1.0]heptane-6-carboxylates |
| dc.contributor.none.fl_str_mv | Universidade do Minho |
| dc.creator.none.fl_str_mv | Alves, M. José Durães, M. Miguel Fortes, A. Gil |
| dc.date.Accepted.fl_str_mv | 2004-01-01T00:00:00Z |
| dc.date.available.fl_str_mv | 2005-05-30T12:53:42Z |
| dc.date.embargoed.fl_str_mv | 2005-05-30T12:53:42Z |
| dc.format.none.fl_str_mv | application/pdf |
| dc.identifier.none.fl_str_mv | https://hdl.handle.net/1822/1841 |
| dc.language.none.fl_str_mv | eng |
| dc.publisher.none.fl_str_mv | Elsevier |
| dc.rights.none.fl_str_mv | http://purl.org/coar/access_right/c_abf2 |
| dc.subject.none.fl_str_mv | 2-azadienes 2H-azirines Diels-alder cycloaddition |
| dc.title.fl_str_mv | Diels-alder cycloaddition of 2-azadienes to methyl 2-(2,6-dichlorophenyl)-2H-azirine-3-carboxylate in the synthesis of methyl 4-oxo-1,3-diazabicyclo[4.1.0]heptane-6-carboxylates |
| dc.type.none.fl_str_mv | http://purl.org/coar/resource_type/c_6501 |
| description | A number of fused 4-oxo-1,3-diazabicyclo[4.1.0]heptane-6-carboxylates, a new type of compound, have been obtained by Diels-Alder cycloaddition between nucleophilic 2-azadienes and an electrophilic 2H-azirine. The reactions are completely endo- and regioselective, the azirine being added by its less hindered face to the diene. There are two isomers 7 and 8 formed from dienes 1 due either to isomerization of the cycloadducts 7 and 8 or by isomerization of the C=N bond of the diene during the reaction. The isomer 10 is formed from diene 2e, and a single diastereoisomer structure 4a-i is formed from dienes 11. Some pyrimidones 8a,7c/8c, 7e, 10, 11d have been hydrolyzed leading to functionalised aziridines 12, 13 and 15. |
| dirty | 0 |
| eu_rights_str_mv | openAccess |
| format | article |
| fulltext.url.fl_str_mv | https://prod-dspace.uminho.pt/bitstreams/b81225b2-adce-4772-9682-c4a8fbd20ed9/download |
| id | rum_cfb965ecc80e4029b9fd3f8d2ffd7e3b |
| identifier.url.fl_str_mv | https://hdl.handle.net/1822/1841 |
| instacron_str | repositorium |
| institution | Universidade do Minho |
| instname_str | Universidade do Minho |
| language | eng |
| network_acronym_str | rum |
| network_name_str | RepositóriUM - Universidade do Minho |
| oai_identifier_str | oai:repositorium.uminho.pt:1822/1841 |
| organization_str_mv | urn:organizationAcronym:repositorium |
| person_str_mv | Alves, M. José Durães, M. Miguel Fortes, A. Gil |
| publishDate | 2004 |
| publisher.none.fl_str_mv | Elsevier |
| reponame_str | RepositóriUM - Universidade do Minho |
| repository_id_str | urn:repositoryAcronym:rum |
| service_str_mv | urn:repositoryAcronym:rum |
| spelling | engElsevierengA number of fused 4-oxo-1,3-diazabicyclo[4.1.0]heptane-6-carboxylates, a new type of compound, have been obtained by Diels-Alder cycloaddition between nucleophilic 2-azadienes and an electrophilic 2H-azirine. The reactions are completely endo- and regioselective, the azirine being added by its less hindered face to the diene. There are two isomers 7 and 8 formed from dienes 1 due either to isomerization of the cycloadducts 7 and 8 or by isomerization of the C=N bond of the diene during the reaction. The isomer 10 is formed from diene 2e, and a single diastereoisomer structure 4a-i is formed from dienes 11. Some pyrimidones 8a,7c/8c, 7e, 10, 11d have been hydrolyzed leading to functionalised aziridines 12, 13 and 15.application/pdfengDiels-alder cycloaddition of 2-azadienes to methyl 2-(2,6-dichlorophenyl)-2H-azirine-3-carboxylate in the synthesis of methyl 4-oxo-1,3-diazabicyclo[4.1.0]heptane-6-carboxylatesAlves, M. JoséDurães, M. MiguelFortes, A. GilHostingInstitutionOrganizationalUniversidade do Minhoe-mailmailto:repositorium@usdb.uminho.ptrepositorium@usdb.uminho.ptISSNIsPartOf0040-4020DOIIsPartOf10.1016/j.tet.2004.06.0042005-05-30T12:53:42Z20042004-01-01T00:00:00ZHandlehttps://hdl.handle.net/1822/1841http://purl.org/coar/access_right/c_abf2open access2-azadienes2H-azirinesDiels-alder cycloaddition170159 bytesliteraturehttp://purl.org/coar/resource_type/c_6501journal articlehttp://purl.org/coar/access_right/c_abf2application/pdffulltexthttps://prod-dspace.uminho.pt/bitstreams/b81225b2-adce-4772-9682-c4a8fbd20ed9/download |
| spellingShingle | Diels-alder cycloaddition of 2-azadienes to methyl 2-(2,6-dichlorophenyl)-2H-azirine-3-carboxylate in the synthesis of methyl 4-oxo-1,3-diazabicyclo[4.1.0]heptane-6-carboxylates Alves, M. José 2-azadienes 2H-azirines Diels-alder cycloaddition |
| status | SINGLETON |
| subject.fl_str_mv | 2-azadienes 2H-azirines Diels-alder cycloaddition |
| title | Diels-alder cycloaddition of 2-azadienes to methyl 2-(2,6-dichlorophenyl)-2H-azirine-3-carboxylate in the synthesis of methyl 4-oxo-1,3-diazabicyclo[4.1.0]heptane-6-carboxylates |
| title_full | Diels-alder cycloaddition of 2-azadienes to methyl 2-(2,6-dichlorophenyl)-2H-azirine-3-carboxylate in the synthesis of methyl 4-oxo-1,3-diazabicyclo[4.1.0]heptane-6-carboxylates |
| title_fullStr | Diels-alder cycloaddition of 2-azadienes to methyl 2-(2,6-dichlorophenyl)-2H-azirine-3-carboxylate in the synthesis of methyl 4-oxo-1,3-diazabicyclo[4.1.0]heptane-6-carboxylates |
| title_full_unstemmed | Diels-alder cycloaddition of 2-azadienes to methyl 2-(2,6-dichlorophenyl)-2H-azirine-3-carboxylate in the synthesis of methyl 4-oxo-1,3-diazabicyclo[4.1.0]heptane-6-carboxylates |
| title_short | Diels-alder cycloaddition of 2-azadienes to methyl 2-(2,6-dichlorophenyl)-2H-azirine-3-carboxylate in the synthesis of methyl 4-oxo-1,3-diazabicyclo[4.1.0]heptane-6-carboxylates |
| title_sort | Diels-alder cycloaddition of 2-azadienes to methyl 2-(2,6-dichlorophenyl)-2H-azirine-3-carboxylate in the synthesis of methyl 4-oxo-1,3-diazabicyclo[4.1.0]heptane-6-carboxylates |
| topic | 2-azadienes 2H-azirines Diels-alder cycloaddition |
| topic_facet | 2-azadienes 2H-azirines Diels-alder cycloaddition |
| url | https://hdl.handle.net/1822/1841 |
| visible | 1 |