Síntese de 1-(selenobutil)-2-fenil-4h-selenofeno[2,3-c]cromenos via reação de ciclização cascata mediada por FeCl3
Ano de defesa: | 2020 |
---|---|
Autor(a) principal: | |
Orientador(a): | |
Banca de defesa: | , |
Tipo de documento: | Dissertação |
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/1/23061 |
Resumo: | The synthesis of heterocyclic compounds is of great importance within the chemistry of materials and the biological area, targeting both the chemical industry and the pharmaceutical industry. Among the different heteroatoms made up of these heterocycles, the selenium atom is capable of bringing different properties to these compounds, mainly in the pharmaceutical area, since most of these heterocyclic compounds contain biological activity. This work aims to synthesize chromene derivatives fused with selenophenes from 1,3-diinyl-aryl-propargyl ethers based on the treatment of these substrates with a mixture of iron (III) chloride and dibutyl diselenide. The same reaction conditions were applied to 1,3-diinyl-aryl-propargylanilines leading to the formation of selenophen quinolines. The reaction parameters were studied and the results obtained were applied to a series of substrates, providing the appropriate products that varied from 33 to 85% of yield. Mechanistic studies indicated that the cooperative action between iron (III) chloride and dibutyl diselenide was essential, having a double action, promoting cyclization and functionalization in the final product with a butylselenoate group. We also proved the synthetic utility of the heterocycles obtained in the Suzukitype cross-coupling reaction, providing the corresponding products coupled with good yields. In addition, the organoselenium portion can be removed from the product structure using n-butyl lithium. Therefore, this work proposed an efficient methodology for the production of twenty-five compounds never reported in the literature, considering a relatively cheap reaction condition with the use of additives that are not harmful to the environment. |
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2021-11-30T11:45:32Z2021-11-30T11:45:32Z2020-02-21http://repositorio.ufsm.br/handle/1/23061The synthesis of heterocyclic compounds is of great importance within the chemistry of materials and the biological area, targeting both the chemical industry and the pharmaceutical industry. Among the different heteroatoms made up of these heterocycles, the selenium atom is capable of bringing different properties to these compounds, mainly in the pharmaceutical area, since most of these heterocyclic compounds contain biological activity. This work aims to synthesize chromene derivatives fused with selenophenes from 1,3-diinyl-aryl-propargyl ethers based on the treatment of these substrates with a mixture of iron (III) chloride and dibutyl diselenide. The same reaction conditions were applied to 1,3-diinyl-aryl-propargylanilines leading to the formation of selenophen quinolines. The reaction parameters were studied and the results obtained were applied to a series of substrates, providing the appropriate products that varied from 33 to 85% of yield. Mechanistic studies indicated that the cooperative action between iron (III) chloride and dibutyl diselenide was essential, having a double action, promoting cyclization and functionalization in the final product with a butylselenoate group. We also proved the synthetic utility of the heterocycles obtained in the Suzukitype cross-coupling reaction, providing the corresponding products coupled with good yields. In addition, the organoselenium portion can be removed from the product structure using n-butyl lithium. Therefore, this work proposed an efficient methodology for the production of twenty-five compounds never reported in the literature, considering a relatively cheap reaction condition with the use of additives that are not harmful to the environment.A síntese de compostos heterocíclicos é de grande importância dentro da química de materiais e da área biológica, visando tanto a indústria química quanto a indústria farmacêutica. Dentre os diversos heteroátomos constituídos nestes heterocíclos, o átomo de selênio é capaz de trazer diversas propriedades para estes compostos, principalmente na área farmacêutica, pois grande parte destes compostos heterocíclicos contêm atividade biológica. Este trabalho tem como objetivo a síntese de derivados de cromeno fundidos com selenofenos a partir de éteres 1,3-diínil-aril-propargílicos baseando-se no tratamento destes substratos com uma mistura de cloreto de ferro (III) e disseleneto de dibutila. As mesmas condições de reação foram aplicadas às 1,3-diínil-arilpropargilanilinas levando à formação de selenofeno quinolinas. Os parâmetros reacionais foram estudados e os resultados obtidos foram aplicados para uma serie de substratos, fornecendo os devidos produtos que variaram de 33 a 85% de rendimento. Os estudos mecanísticos indicaram que a ação cooperativa entre o cloreto de ferro (III) e o disseleneto de dibutila foi essencial, tendo uma ação dupla, promovendo a ciclização e a funcionalização no produto final com um grupamento butilselenoato. Ainda provamos a utilidade sintética dos heterociclos obtidos na reação de acoplamento cruzado do tipo Suzuki, fornecendo os produtos correspondentes acoplados com bons rendimentos. Além disso, a porção organosselênio pode ser removida da estrutura do produto usando n-butil-lítio. Por conseguinte, este trabalho propôs uma metodologia eficiente para a produção de vinte e cinco compostos nunca relatados na literatura, tendo em vista uma condição reacional relativamente barata com a utilização de aditivos não nocivos ao meio ambiente.Coordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPESporUniversidade 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/openAccessCromenosSelenofenosDisselenetosSelenetosHeterociclosFerroChromenesSelenophenesDiselenidesSelenidesHeterocyclesIronCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese de 1-(selenobutil)-2-fenil-4h-selenofeno[2,3-c]cromenos via reação de ciclização cascata mediada por FeCl3Synthesis of 1- (selenobutile) -2-phenyl-4h-selenophene [2,3-c] chromes via FeCl3 mediated cycle reactioninfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisZeni, Gilson Rogériohttp://lattes.cnpq.br/2355575631197937Schumacher, Ricardo FredericoFernandes, Liana da SilvaMendes, Samuel Rodrigueshttp://lattes.cnpq.br/5421408026280347Silva, Guilherme Lutz da100600000000600600600600600600b35c9860-bf5d-4c8a-ab16-02ed6931c067e30f955d-8324-4b6c-a66f-1e3f0ffcd4f17fba4d72-f46d-4f2d-a8cc-3b2aae8b7f2d382563b5-0585-486b-a7a3-07dcac36dcc910fc2a99-9f62-43a4-b380-53ccea1ab31ereponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMCC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; 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dc.title.por.fl_str_mv |
Síntese de 1-(selenobutil)-2-fenil-4h-selenofeno[2,3-c]cromenos via reação de ciclização cascata mediada por FeCl3 |
dc.title.alternative.eng.fl_str_mv |
Synthesis of 1- (selenobutile) -2-phenyl-4h-selenophene [2,3-c] chromes via FeCl3 mediated cycle reaction |
title |
Síntese de 1-(selenobutil)-2-fenil-4h-selenofeno[2,3-c]cromenos via reação de ciclização cascata mediada por FeCl3 |
spellingShingle |
Síntese de 1-(selenobutil)-2-fenil-4h-selenofeno[2,3-c]cromenos via reação de ciclização cascata mediada por FeCl3 Silva, Guilherme Lutz da Cromenos Selenofenos Disselenetos Selenetos Heterociclos Ferro Chromenes Selenophenes Diselenides Selenides Heterocycles Iron CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Síntese de 1-(selenobutil)-2-fenil-4h-selenofeno[2,3-c]cromenos via reação de ciclização cascata mediada por FeCl3 |
title_full |
Síntese de 1-(selenobutil)-2-fenil-4h-selenofeno[2,3-c]cromenos via reação de ciclização cascata mediada por FeCl3 |
title_fullStr |
Síntese de 1-(selenobutil)-2-fenil-4h-selenofeno[2,3-c]cromenos via reação de ciclização cascata mediada por FeCl3 |
title_full_unstemmed |
Síntese de 1-(selenobutil)-2-fenil-4h-selenofeno[2,3-c]cromenos via reação de ciclização cascata mediada por FeCl3 |
title_sort |
Síntese de 1-(selenobutil)-2-fenil-4h-selenofeno[2,3-c]cromenos via reação de ciclização cascata mediada por FeCl3 |
author |
Silva, Guilherme Lutz da |
author_facet |
Silva, Guilherme Lutz da |
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.advisor-co1.fl_str_mv |
Schumacher, Ricardo Frederico |
dc.contributor.referee1.fl_str_mv |
Fernandes, Liana da Silva |
dc.contributor.referee2.fl_str_mv |
Mendes, Samuel Rodrigues |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/5421408026280347 |
dc.contributor.author.fl_str_mv |
Silva, Guilherme Lutz da |
contributor_str_mv |
Zeni, Gilson Rogério Schumacher, Ricardo Frederico Fernandes, Liana da Silva Mendes, Samuel Rodrigues |
dc.subject.por.fl_str_mv |
Cromenos Selenofenos Disselenetos Selenetos Heterociclos Ferro |
topic |
Cromenos Selenofenos Disselenetos Selenetos Heterociclos Ferro Chromenes Selenophenes Diselenides Selenides Heterocycles Iron CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.eng.fl_str_mv |
Chromenes Selenophenes Diselenides Selenides Heterocycles Iron |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
The synthesis of heterocyclic compounds is of great importance within the chemistry of materials and the biological area, targeting both the chemical industry and the pharmaceutical industry. Among the different heteroatoms made up of these heterocycles, the selenium atom is capable of bringing different properties to these compounds, mainly in the pharmaceutical area, since most of these heterocyclic compounds contain biological activity. This work aims to synthesize chromene derivatives fused with selenophenes from 1,3-diinyl-aryl-propargyl ethers based on the treatment of these substrates with a mixture of iron (III) chloride and dibutyl diselenide. The same reaction conditions were applied to 1,3-diinyl-aryl-propargylanilines leading to the formation of selenophen quinolines. The reaction parameters were studied and the results obtained were applied to a series of substrates, providing the appropriate products that varied from 33 to 85% of yield. Mechanistic studies indicated that the cooperative action between iron (III) chloride and dibutyl diselenide was essential, having a double action, promoting cyclization and functionalization in the final product with a butylselenoate group. We also proved the synthetic utility of the heterocycles obtained in the Suzukitype cross-coupling reaction, providing the corresponding products coupled with good yields. In addition, the organoselenium portion can be removed from the product structure using n-butyl lithium. Therefore, this work proposed an efficient methodology for the production of twenty-five compounds never reported in the literature, considering a relatively cheap reaction condition with the use of additives that are not harmful to the environment. |
publishDate |
2020 |
dc.date.issued.fl_str_mv |
2020-02-21 |
dc.date.accessioned.fl_str_mv |
2021-11-30T11:45:32Z |
dc.date.available.fl_str_mv |
2021-11-30T11:45:32Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/masterThesis |
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masterThesis |
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publishedVersion |
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http://repositorio.ufsm.br/handle/1/23061 |
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http://repositorio.ufsm.br/handle/1/23061 |
dc.language.iso.fl_str_mv |
por |
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por |
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100600000000 |
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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 |
rights_invalid_str_mv |
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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