Síntese de derivados de benzo[b]furanos via dupla ciclização intramolecular promovida por t-BuOK
Ano de defesa: | 2016 |
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Autor(a) principal: | |
Orientador(a): | |
Banca de defesa: | , , , |
Tipo de documento: | Tese |
Tipo de acesso: | Acesso aberto |
Idioma: | por |
Instituição de defesa: |
Universidade Federal de Santa Maria
Centro de Ciências Naturais e Exatas |
Programa de Pós-Graduação: |
Programa de Pós-Graduação em Química
|
Departamento: |
Química
|
País: |
Brasil
|
Palavras-chave em Português: | |
Palavras-chave em Inglês: | |
Área do conhecimento CNPq: | |
Link de acesso: | http://repositorio.ufsm.br/handle/1/21521 |
Resumo: | In this work, we reported the developed study for the preparation of substituted benzo[b]furans via double anionic intramolecular cyclization process promoted by t-BuOK. Firstly, a variety of 5H-benzo[d]benzofuro[3,2-b]azepines 2 was prepared by the reaction of 2-((2- ethynyl)benzyloxy)benzonitriles 1 with a catalytic amount of t-BuOK (Equation 1). Subsequently, the aryldiynes 3 were subjected to carbocyclization reaction promoted by t- BuOK, which allowed the synthesis of 5aH-benzo[4,5]cyclohepta[1,2-b]benzofurans 4 in good yields (Equation 2). Both methodologies proceeded selectively through a 5-exo-dig intramolecular cyclization followed by a 7-endo-dig cyclization furnishing the benzo[b]furans in a one pot procedure. |
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Biblioteca Digital de Teses e Dissertações do UFSM |
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2021-07-19T20:13:12Z2021-07-19T20:13:12Z2016-09-23http://repositorio.ufsm.br/handle/1/21521In this work, we reported the developed study for the preparation of substituted benzo[b]furans via double anionic intramolecular cyclization process promoted by t-BuOK. Firstly, a variety of 5H-benzo[d]benzofuro[3,2-b]azepines 2 was prepared by the reaction of 2-((2- ethynyl)benzyloxy)benzonitriles 1 with a catalytic amount of t-BuOK (Equation 1). Subsequently, the aryldiynes 3 were subjected to carbocyclization reaction promoted by t- BuOK, which allowed the synthesis of 5aH-benzo[4,5]cyclohepta[1,2-b]benzofurans 4 in good yields (Equation 2). Both methodologies proceeded selectively through a 5-exo-dig intramolecular cyclization followed by a 7-endo-dig cyclization furnishing the benzo[b]furans in a one pot procedure.Neste trabalho, relata-se o estudo desenvolvido para a preparação de benzo[b]furanos substituídos via processo de dupla ciclização intramolecular aniônica promovido por t-BuOK. Primeiramente, uma variedade de 5H-benzo[d]benzofuro[3,2-b]azepinos 2 foi preparada através da reação das 2-((2-etinil)benziloxi)benzonitrilas 1 com quantidades catalíticas de t- BuOK (Equação 1). Posteriormente, os arildiinos 3 foram submetidos à reação de carbociclização com t-BuOK, o que permitiu a síntese dos 5aH-benzo[4,5]ciclohepta[1,2- b]benzofuranos 4 em bons rendimentos (Equação 2). Ambas metodologias desenvolvidas ocorreram seletivamente através de uma ciclização intramolecular 5-exo-dig seguida de uma ciclização 7-endo-dig, fornecendo os benzo[b]furanos em um procedimento one pot.porUniversidade Federal de Santa MariaCentro de Ciências Naturais e ExatasPrograma de Pós-Graduação em QuímicaUFSMBrasilQuímicaAttribution-NonCommercial-NoDerivatives 4.0 Internationalhttp://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccessCiclizaçãoBenzo[b]furanosHeterociclosCyclizationBenzo[b]furansHeterocyclesCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese de derivados de benzo[b]furanos via dupla ciclização intramolecular promovida por t-BuOKSynthesis of benzo[b]furans derivatives via double intramolecular cyclization promoted by t-BuOKinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisZeni, Gilson Rogériohttp://lattes.cnpq.br/2355575631197937Godoi, Benhur deDornelles, LucianoGariani, Rogério AparecidoSilva, Thiago Barcellos daXXXXXXXXXXXXXXXXGai, Rafaela Mozzaquatro10060000000060060060060060040bcc34b-9304-4b92-ba5d-b8aeb3962ae98efa93e8-8aad-4141-8e47-b79c0bc4732f73af17fe-4603-4a92-9890-9ab29a107d4e4a671e0c-bfb0-436b-bd8f-ab5645f4229ec26063e5-054d-44b3-adff-c8705366db04b15d8bc3-9be3-4fcc-a89c-53eeee7d7510reponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALTES_PPGQUIMICA_2016_GAI_RAFAELA.pdfTES_PPGQUIMICA_2016_GAI_RAFAELA.pdfTese de Doutoradoapplication/pdf26414589http://repositorio.ufsm.br/bitstream/1/21521/1/TES_PPGQUIMICA_2016_GAI_RAFAELA.pdf0a791846d445601cac9aa33194532347MD51CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; 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dc.title.por.fl_str_mv |
Síntese de derivados de benzo[b]furanos via dupla ciclização intramolecular promovida por t-BuOK |
dc.title.alternative.eng.fl_str_mv |
Synthesis of benzo[b]furans derivatives via double intramolecular cyclization promoted by t-BuOK |
title |
Síntese de derivados de benzo[b]furanos via dupla ciclização intramolecular promovida por t-BuOK |
spellingShingle |
Síntese de derivados de benzo[b]furanos via dupla ciclização intramolecular promovida por t-BuOK Gai, Rafaela Mozzaquatro Ciclização Benzo[b]furanos Heterociclos Cyclization Benzo[b]furans Heterocycles CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Síntese de derivados de benzo[b]furanos via dupla ciclização intramolecular promovida por t-BuOK |
title_full |
Síntese de derivados de benzo[b]furanos via dupla ciclização intramolecular promovida por t-BuOK |
title_fullStr |
Síntese de derivados de benzo[b]furanos via dupla ciclização intramolecular promovida por t-BuOK |
title_full_unstemmed |
Síntese de derivados de benzo[b]furanos via dupla ciclização intramolecular promovida por t-BuOK |
title_sort |
Síntese de derivados de benzo[b]furanos via dupla ciclização intramolecular promovida por t-BuOK |
author |
Gai, Rafaela Mozzaquatro |
author_facet |
Gai, Rafaela Mozzaquatro |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Zeni, Gilson Rogério |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/2355575631197937 |
dc.contributor.referee1.fl_str_mv |
Godoi, Benhur de |
dc.contributor.referee2.fl_str_mv |
Dornelles, Luciano |
dc.contributor.referee3.fl_str_mv |
Gariani, Rogério Aparecido |
dc.contributor.referee4.fl_str_mv |
Silva, Thiago Barcellos da |
dc.contributor.authorLattes.fl_str_mv |
XXXXXXXXXXXXXXXX |
dc.contributor.author.fl_str_mv |
Gai, Rafaela Mozzaquatro |
contributor_str_mv |
Zeni, Gilson Rogério Godoi, Benhur de Dornelles, Luciano Gariani, Rogério Aparecido Silva, Thiago Barcellos da |
dc.subject.por.fl_str_mv |
Ciclização Benzo[b]furanos Heterociclos |
topic |
Ciclização Benzo[b]furanos Heterociclos Cyclization Benzo[b]furans Heterocycles CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.eng.fl_str_mv |
Cyclization Benzo[b]furans Heterocycles |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
In this work, we reported the developed study for the preparation of substituted benzo[b]furans via double anionic intramolecular cyclization process promoted by t-BuOK. Firstly, a variety of 5H-benzo[d]benzofuro[3,2-b]azepines 2 was prepared by the reaction of 2-((2- ethynyl)benzyloxy)benzonitriles 1 with a catalytic amount of t-BuOK (Equation 1). Subsequently, the aryldiynes 3 were subjected to carbocyclization reaction promoted by t- BuOK, which allowed the synthesis of 5aH-benzo[4,5]cyclohepta[1,2-b]benzofurans 4 in good yields (Equation 2). Both methodologies proceeded selectively through a 5-exo-dig intramolecular cyclization followed by a 7-endo-dig cyclization furnishing the benzo[b]furans in a one pot procedure. |
publishDate |
2016 |
dc.date.issued.fl_str_mv |
2016-09-23 |
dc.date.accessioned.fl_str_mv |
2021-07-19T20:13:12Z |
dc.date.available.fl_str_mv |
2021-07-19T20:13:12Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/doctoralThesis |
format |
doctoralThesis |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://repositorio.ufsm.br/handle/1/21521 |
url |
http://repositorio.ufsm.br/handle/1/21521 |
dc.language.iso.fl_str_mv |
por |
language |
por |
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100600000000 |
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600 600 600 600 600 |
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Attribution-NonCommercial-NoDerivatives 4.0 International http://creativecommons.org/licenses/by-nc-nd/4.0/ info:eu-repo/semantics/openAccess |
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Attribution-NonCommercial-NoDerivatives 4.0 International http://creativecommons.org/licenses/by-nc-nd/4.0/ |
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openAccess |
dc.publisher.none.fl_str_mv |
Universidade Federal de Santa Maria Centro de Ciências Naturais e Exatas |
dc.publisher.program.fl_str_mv |
Programa de Pós-Graduação em Química |
dc.publisher.initials.fl_str_mv |
UFSM |
dc.publisher.country.fl_str_mv |
Brasil |
dc.publisher.department.fl_str_mv |
Química |
publisher.none.fl_str_mv |
Universidade Federal de Santa Maria Centro de Ciências Naturais e Exatas |
dc.source.none.fl_str_mv |
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