Intramolecular addition of acyldiazenecarboxylates onto double bonds in the synthesis of heterocycles

Detalhes bibliográficos
Autor(a) principal: Prata, José V.
Data de Publicação: 2002
Outros Autores: Clemente, Dina-Telma S., Prabhakar, Sundaresan, Lobo, Ana M., Mourato, Isabel, Branco, Paula Sério
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10400.21/11815
Resumo: Appropriate aryl-substituted unsymmetrical azodicarbonyl compounds, generated from bishydrazides by oxidation, undergo intramolecular cyclisations to furnish a variety of useful heterocycles such as N-substituted oxindoles, carbostyrils, benzazepinones, benzazocinones, benzimidazolones, benzoxazinones and pyrazolones in varying degrees of efficiency. Methods are described to remove the N-acyl groups from the heteroaromatic compounds. Under mildly acidic conditions where equal opportunities are available for an ipso or a normal cyclisation it is the former process that occurs preferentially. Evidence is presented in favour of a C-to-C migration in the ipso product for the formation of a methoxy-substituted carbostyril derivative. One of the spiro substances is shown to participate in dienone–phenol rearrangement to provide the corresponding quinolone–phenol in high yield.
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spelling Intramolecular addition of acyldiazenecarboxylates onto double bonds in the synthesis of heterocyclesIntramolecularAcyldiazenecarboxylatesSynthesisHeterocyclesAppropriate aryl-substituted unsymmetrical azodicarbonyl compounds, generated from bishydrazides by oxidation, undergo intramolecular cyclisations to furnish a variety of useful heterocycles such as N-substituted oxindoles, carbostyrils, benzazepinones, benzazocinones, benzimidazolones, benzoxazinones and pyrazolones in varying degrees of efficiency. Methods are described to remove the N-acyl groups from the heteroaromatic compounds. Under mildly acidic conditions where equal opportunities are available for an ipso or a normal cyclisation it is the former process that occurs preferentially. Evidence is presented in favour of a C-to-C migration in the ipso product for the formation of a methoxy-substituted carbostyril derivative. One of the spiro substances is shown to participate in dienone–phenol rearrangement to provide the corresponding quinolone–phenol in high yield.Royal Society of ChemistryRCIPLPrata, José V.Clemente, Dina-Telma S.Prabhakar, SundaresanLobo, Ana M.Mourato, IsabelBranco, Paula Sério2020-06-09T18:15:06Z2002-01-232002-01-23T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10400.21/11815engPRATA, José V.; [et al] – Intramolecular addition of acyldiazenecarboxylates onto double bonds in the synthesis of heterocycles. Journal of the Chemical Society, Perkin Transactions 1. ISSN 1470-4358. N.º 4 (2002), pp. 513-5281470-435810.1039/B110414Dmetadata only accessinfo: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:RCAAP2023-08-03T10:03:32Zoai:repositorio.ipl.pt:10400.21/11815Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T20:19:59.562649Repositório 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 Intramolecular addition of acyldiazenecarboxylates onto double bonds in the synthesis of heterocycles
title Intramolecular addition of acyldiazenecarboxylates onto double bonds in the synthesis of heterocycles
spellingShingle Intramolecular addition of acyldiazenecarboxylates onto double bonds in the synthesis of heterocycles
Prata, José V.
Intramolecular
Acyldiazenecarboxylates
Synthesis
Heterocycles
title_short Intramolecular addition of acyldiazenecarboxylates onto double bonds in the synthesis of heterocycles
title_full Intramolecular addition of acyldiazenecarboxylates onto double bonds in the synthesis of heterocycles
title_fullStr Intramolecular addition of acyldiazenecarboxylates onto double bonds in the synthesis of heterocycles
title_full_unstemmed Intramolecular addition of acyldiazenecarboxylates onto double bonds in the synthesis of heterocycles
title_sort Intramolecular addition of acyldiazenecarboxylates onto double bonds in the synthesis of heterocycles
author Prata, José V.
author_facet Prata, José V.
Clemente, Dina-Telma S.
Prabhakar, Sundaresan
Lobo, Ana M.
Mourato, Isabel
Branco, Paula Sério
author_role author
author2 Clemente, Dina-Telma S.
Prabhakar, Sundaresan
Lobo, Ana M.
Mourato, Isabel
Branco, Paula Sério
author2_role author
author
author
author
author
dc.contributor.none.fl_str_mv RCIPL
dc.contributor.author.fl_str_mv Prata, José V.
Clemente, Dina-Telma S.
Prabhakar, Sundaresan
Lobo, Ana M.
Mourato, Isabel
Branco, Paula Sério
dc.subject.por.fl_str_mv Intramolecular
Acyldiazenecarboxylates
Synthesis
Heterocycles
topic Intramolecular
Acyldiazenecarboxylates
Synthesis
Heterocycles
description Appropriate aryl-substituted unsymmetrical azodicarbonyl compounds, generated from bishydrazides by oxidation, undergo intramolecular cyclisations to furnish a variety of useful heterocycles such as N-substituted oxindoles, carbostyrils, benzazepinones, benzazocinones, benzimidazolones, benzoxazinones and pyrazolones in varying degrees of efficiency. Methods are described to remove the N-acyl groups from the heteroaromatic compounds. Under mildly acidic conditions where equal opportunities are available for an ipso or a normal cyclisation it is the former process that occurs preferentially. Evidence is presented in favour of a C-to-C migration in the ipso product for the formation of a methoxy-substituted carbostyril derivative. One of the spiro substances is shown to participate in dienone–phenol rearrangement to provide the corresponding quinolone–phenol in high yield.
publishDate 2002
dc.date.none.fl_str_mv 2002-01-23
2002-01-23T00:00:00Z
2020-06-09T18:15:06Z
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/10400.21/11815
url http://hdl.handle.net/10400.21/11815
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv PRATA, José V.; [et al] – Intramolecular addition of acyldiazenecarboxylates onto double bonds in the synthesis of heterocycles. Journal of the Chemical Society, Perkin Transactions 1. ISSN 1470-4358. N.º 4 (2002), pp. 513-528
1470-4358
10.1039/B110414D
dc.rights.driver.fl_str_mv metadata only access
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rights_invalid_str_mv metadata only access
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Royal Society of Chemistry
publisher.none.fl_str_mv Royal Society of Chemistry
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
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instname_str Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
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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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