Síntese de derivados de furanos e isocalcogenocromenos via ciclização eletrofílica
Ano de defesa: | 2010 |
---|---|
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: | |
Área do conhecimento CNPq: | |
Link de acesso: | http://repositorio.ufsm.br/handle/1/21626 |
Resumo: | In this work, a range of (Z)-enynols 4 was prepared from telluroenynes 1 via tellurium-lithium exchange reaction followed by addition of different aldehydes or ketones. Subsequently the substrate 4 was subjected to an electrophilic intramolecular cyclization mediated by palladium salt. This methodology allowed the preparation of functionalized 2,5-dihydrofuran 5 and furan derivates 6, furnishing the corresponding products in good yields. After that, we developed a methodology to obtain isochalcogenchromenes 10 via electrophilic cyclization reaction of 2-alkynylbenzylchalcogenides 9. Using this protocol, a series of 2-alkynylbenzylchalcogenides 9 was prepared by substitution reaction with anions alkylchalcogenolates, followed by Sonogashira cross-couplig reaction. Subsequently, these substrates were cyclized with electrophiles, such as I2, furnishing the correspondent products in moderate to good yields. |
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Biblioteca Digital de Teses e Dissertações do UFSM |
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2021-07-28T17:18:59Z2021-07-28T17:18:59Z2010-09-24http://repositorio.ufsm.br/handle/1/21626In this work, a range of (Z)-enynols 4 was prepared from telluroenynes 1 via tellurium-lithium exchange reaction followed by addition of different aldehydes or ketones. Subsequently the substrate 4 was subjected to an electrophilic intramolecular cyclization mediated by palladium salt. This methodology allowed the preparation of functionalized 2,5-dihydrofuran 5 and furan derivates 6, furnishing the corresponding products in good yields. After that, we developed a methodology to obtain isochalcogenchromenes 10 via electrophilic cyclization reaction of 2-alkynylbenzylchalcogenides 9. Using this protocol, a series of 2-alkynylbenzylchalcogenides 9 was prepared by substitution reaction with anions alkylchalcogenolates, followed by Sonogashira cross-couplig reaction. Subsequently, these substrates were cyclized with electrophiles, such as I2, furnishing the correspondent products in moderate to good yields.No presente trabalho, uma série de (Z)-eninóis 4 foi preparada a partir de teluroeninos 1, via reação de transmetalação telúrio-lítio seguido da captura com diferentes aldeídos ou cetonas. Posteriormente o substrato 4 foi submetido a ciclização eletrofílica intramolecular, mediada por sal de paládio. Esta metodologia permitiu a obtenção de derivados de 2,5-diidrofuranos 5 e furanos 6 funcionalizados, fornecendo os respectivos produtos em bons rendimentos. Em uma segunda etapa do trabalho desenvolveu-se uma metodologia de obtenção de derivados de isocalcogenocromenos 10, via reação de ciclização eletrofílica de 2-alquinilbenzilcalcogenetos 9. Utilizando-se este protocolo, uma série de 2-alquinilbenzilcalcogenetos 9 foi preparada através de reação de substituição com ânions alquilcalcogenolatos, seguido de reação de acoplamento do tipo Sonogashira. Posteriormente, estes substratos foram ciclizados com eletrófilos, como I2, fornecendo os respectivos produtos em rendimentos moderados a bons.Conselho Nacional de Pesquisa e Desenvolvimento Científico e Tecnológico - CNPqCoordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPESFundação de Amparo à Pesquisa do Estado do Rio Grande do Sul - FAPERGSporUniversidade 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/openAccessFuranosCiclização eletrofílicaCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese de derivados de furanos e isocalcogenocromenos via ciclização eletrofílicaSynthesis of furan and isochalcogenchromene derivatives via electrophilic cyclizationinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisZeni, Gilson Rogériohttp://lattes.cnpq.br/2355575631197937Braga, Antonio LuizSchneider, Paulo HenriqueJacob, Raquel GuimarãesDornelles, Lucianohttp://lattes.cnpq.br/2305432767739828Schneider, Caroline Cassalha10060000000060060060060060060060040bcc34b-9304-4b92-ba5d-b8aeb3962ae92fdfd9b8-577b-4735-bb27-9c84ec73eeed70895f0d-f6c9-4428-81ac-bad500be1dc55b7ce564-4a53-4527-8734-1771cfa1f522b976a2fc-6d5b-4ae3-9b55-1cd4002604a26f6ca89d-dfdf-41bb-9190-ea786a030c67reponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALTES_PPGQUIMICA_2010_SCHNEIDER_CAROLINE.pdfTES_PPGQUIMICA_2010_SCHNEIDER_CAROLINE.pdfTeseapplication/pdf21941118http://repositorio.ufsm.br/bitstream/1/21626/1/TES_PPGQUIMICA_2010_SCHNEIDER_CAROLINE.pdffab7415ed9596e91e259b2bfd31bd6acMD51CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; 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dc.title.por.fl_str_mv |
Síntese de derivados de furanos e isocalcogenocromenos via ciclização eletrofílica |
dc.title.alternative.eng.fl_str_mv |
Synthesis of furan and isochalcogenchromene derivatives via electrophilic cyclization |
title |
Síntese de derivados de furanos e isocalcogenocromenos via ciclização eletrofílica |
spellingShingle |
Síntese de derivados de furanos e isocalcogenocromenos via ciclização eletrofílica Schneider, Caroline Cassalha Furanos Ciclização eletrofílica CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Síntese de derivados de furanos e isocalcogenocromenos via ciclização eletrofílica |
title_full |
Síntese de derivados de furanos e isocalcogenocromenos via ciclização eletrofílica |
title_fullStr |
Síntese de derivados de furanos e isocalcogenocromenos via ciclização eletrofílica |
title_full_unstemmed |
Síntese de derivados de furanos e isocalcogenocromenos via ciclização eletrofílica |
title_sort |
Síntese de derivados de furanos e isocalcogenocromenos via ciclização eletrofílica |
author |
Schneider, Caroline Cassalha |
author_facet |
Schneider, Caroline Cassalha |
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 |
Braga, Antonio Luiz |
dc.contributor.referee2.fl_str_mv |
Schneider, Paulo Henrique |
dc.contributor.referee3.fl_str_mv |
Jacob, Raquel Guimarães |
dc.contributor.referee4.fl_str_mv |
Dornelles, Luciano |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/2305432767739828 |
dc.contributor.author.fl_str_mv |
Schneider, Caroline Cassalha |
contributor_str_mv |
Zeni, Gilson Rogério Braga, Antonio Luiz Schneider, Paulo Henrique Jacob, Raquel Guimarães Dornelles, Luciano |
dc.subject.por.fl_str_mv |
Furanos Ciclização eletrofílica |
topic |
Furanos Ciclização eletrofílica CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
In this work, a range of (Z)-enynols 4 was prepared from telluroenynes 1 via tellurium-lithium exchange reaction followed by addition of different aldehydes or ketones. Subsequently the substrate 4 was subjected to an electrophilic intramolecular cyclization mediated by palladium salt. This methodology allowed the preparation of functionalized 2,5-dihydrofuran 5 and furan derivates 6, furnishing the corresponding products in good yields. After that, we developed a methodology to obtain isochalcogenchromenes 10 via electrophilic cyclization reaction of 2-alkynylbenzylchalcogenides 9. Using this protocol, a series of 2-alkynylbenzylchalcogenides 9 was prepared by substitution reaction with anions alkylchalcogenolates, followed by Sonogashira cross-couplig reaction. Subsequently, these substrates were cyclized with electrophiles, such as I2, furnishing the correspondent products in moderate to good yields. |
publishDate |
2010 |
dc.date.issued.fl_str_mv |
2010-09-24 |
dc.date.accessioned.fl_str_mv |
2021-07-28T17:18:59Z |
dc.date.available.fl_str_mv |
2021-07-28T17:18:59Z |
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/1/21626 |
url |
http://repositorio.ufsm.br/handle/1/21626 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.relation.cnpq.fl_str_mv |
100600000000 |
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600 600 600 600 600 600 600 |
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dc.rights.driver.fl_str_mv |
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/ |
eu_rights_str_mv |
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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