Síntese de 4,5-bis(trifluormetil)-1h-pirazóis através de reações eletrofílicas e nucleofílicas empregando NIS e MFSDA
Ano de defesa: | 2019 |
---|---|
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/1/16761 |
Resumo: | This dissertation describes the development of an efficient methodology for the functionalization of position 4 of 3-alkyl(aryl)-1-aryl-5-trifluoromethyl-1H-pyrazoles systems by halogenation and subsequent reaction with trifluoromethylating reagent MFSDA, thus obtaining a series of six unpublished examples of 4-iodo-5-trifluoromethyl-1H -pyrazoles in addition to seven unpublished compounds of the 4,5- bis(trifluoromethyl)-1H-pyrazoles series. Initially eight examples of 1-aryl-3-alkyl (aryl) -5-trifluoromethyl-1H-pyrazoles where aryl = C6H5, 4-FC6H4, 4-ClC6H4 and alkyl = Me, c-Pr, i-Pr, n-Bu from the cyclocondensation reaction [3 + 2] between 4-alkyl (aryl) -4-alkoxy-1,1,1-trifluoro-3-alken-2-ones and arylhydrazines in yields of 91-94%. The synthesized starting materials were then subjected to CF3COOH -catalyzed electrophilic iodination using the N-iodosuccinimide (NIS) reagent resulting in a series of 4-iodo-5-trifluoromethyl-1H-pyrazoles in yields of 75-87%. Subsequently the optimization of the methodology of insertion of trifluoromethyl at the 4-position of the series of 4-iodo-5-trifluoromethyl-1H-pyrazoles through nucleophilic substitution using the MFSDA reagent was performed. For this, different copper salts and additives were tested, besides the study of the reaction in argon atmosphere. By optimizing the methodology it was possible to synthesize an unpublished series of 4,5-bis(trifluoromethyl)-1H-pyrazoles in yields of up to 79%. |
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Biblioteca Digital de Teses e Dissertações do UFSM |
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|
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2019-06-05T20:50:02Z2019-06-05T20:50:02Z2019-02-27http://repositorio.ufsm.br/handle/1/16761This dissertation describes the development of an efficient methodology for the functionalization of position 4 of 3-alkyl(aryl)-1-aryl-5-trifluoromethyl-1H-pyrazoles systems by halogenation and subsequent reaction with trifluoromethylating reagent MFSDA, thus obtaining a series of six unpublished examples of 4-iodo-5-trifluoromethyl-1H -pyrazoles in addition to seven unpublished compounds of the 4,5- bis(trifluoromethyl)-1H-pyrazoles series. Initially eight examples of 1-aryl-3-alkyl (aryl) -5-trifluoromethyl-1H-pyrazoles where aryl = C6H5, 4-FC6H4, 4-ClC6H4 and alkyl = Me, c-Pr, i-Pr, n-Bu from the cyclocondensation reaction [3 + 2] between 4-alkyl (aryl) -4-alkoxy-1,1,1-trifluoro-3-alken-2-ones and arylhydrazines in yields of 91-94%. The synthesized starting materials were then subjected to CF3COOH -catalyzed electrophilic iodination using the N-iodosuccinimide (NIS) reagent resulting in a series of 4-iodo-5-trifluoromethyl-1H-pyrazoles in yields of 75-87%. Subsequently the optimization of the methodology of insertion of trifluoromethyl at the 4-position of the series of 4-iodo-5-trifluoromethyl-1H-pyrazoles through nucleophilic substitution using the MFSDA reagent was performed. For this, different copper salts and additives were tested, besides the study of the reaction in argon atmosphere. By optimizing the methodology it was possible to synthesize an unpublished series of 4,5-bis(trifluoromethyl)-1H-pyrazoles in yields of up to 79%.Esta dissertação descreve o desenvolvimento de uma metodologia eficiente na funcionalização da posição 4 de sistemas 3-alquil(aril)-1-aril-5-trifluormetil-1H-pirazóis através da halogenação e posterior reação com reagente trifluormetilante MFSDA, sendo possível, deste modo, a obtenção de uma série de seis exemplos inéditos de 4-iodo-5-trifluormetil-1H-pirazóis além de sete compostos inéditos da série de 4,5-bis(trifluormetil)-1H-pirazóis. Inicialmente foram sintetizados oito exemplos de 1-aril-3-alquil(aril)-5-trifluormetil-1H-pirazóis onde aril= C6H5, 4-FC6H4, 4-ClC6H4 e alquil= Me, c-Pr, i-Pr, n-Bu, a partir de reação de ciclocondensação [3+2] entre 4-alquil(aril)-4-alcóxi-1,1,1-triflúor-3-alquen-2-onas e arilhidrazinas com rendimentos de 91-94%. A seguir os materiais de partida sintetizados foram submetidos a iodação eletrofílica catalisada por CF3COOH utilizando o reagente N-iodosuccinimida (NIS) resultando em uma série de 4-iodo-5-trifluormetil-1H-pirazóis com rendimentos de 75-87%. Subsequentemente foi realizada a otimização da metodologia de inserção de trifluormetila na posição 4 da série de 4-iodo-5-trifluormetil-1H-pirazóis através de substituição nucleofílica utilizando o reagente MFSDA. Para tanto, foram testados diferentes sais de cobre e uso de aditivos, além do estudo da reação em atmosfera de argônio. Com a otimização da metodologia foi possível a síntese de uma série inédita de 4,5-bis(trifluormetil)-1H-pirazóis com rendimentos de até 79%.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/openAccessPirazóisReação de iodaçãoNISReação de trifluormetilaçãoMFSDABis(trifluormetil)PyrazolesIodination reactionTrifluoromethylation reactionBis(trifluoromethyl)CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese de 4,5-bis(trifluormetil)-1h-pirazóis através de reações eletrofílicas e nucleofílicas empregando NIS e MFSDASynthesis of 4,5-bis(trifluoromethyl)-1h-pyrazoles through electrophylic and nucleofylic reactions employing NIS and MFSDAinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisBonacorso, Helio Gauzehttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4788537E0Fantinel, Leonardohttp://lattes.cnpq.br/3934644027018397Severo Filho, Wolmar Alípiohttp://lattes.cnpq.br/1999826579939679http://lattes.cnpq.br/3902571039171981Junges, Andrizia de Freitas10060000000060006c852ad-d805-43c3-99d6-93a6a86f507ca4f46a68-70dc-4ccb-bd93-8795539cec67b0e1e2a5-71c6-4a3f-9161-9fa6805b8b49a07c475c-60f3-4ff9-bff8-2a4f54329a61reponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALDIS_PPGQUIMICA_2019_JUNGES_ANDRIZIA.pdfDIS_PPGQUIMICA_2019_JUNGES_ANDRIZIA.pdfDissertação de Mestradoapplication/pdf5508820http://repositorio.ufsm.br/bitstream/1/16761/1/DIS_PPGQUIMICA_2019_JUNGES_ANDRIZIA.pdf53bbea957d489e658ad55afc6c63dcd5MD51CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; 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dc.title.por.fl_str_mv |
Síntese de 4,5-bis(trifluormetil)-1h-pirazóis através de reações eletrofílicas e nucleofílicas empregando NIS e MFSDA |
dc.title.alternative.eng.fl_str_mv |
Synthesis of 4,5-bis(trifluoromethyl)-1h-pyrazoles through electrophylic and nucleofylic reactions employing NIS and MFSDA |
title |
Síntese de 4,5-bis(trifluormetil)-1h-pirazóis através de reações eletrofílicas e nucleofílicas empregando NIS e MFSDA |
spellingShingle |
Síntese de 4,5-bis(trifluormetil)-1h-pirazóis através de reações eletrofílicas e nucleofílicas empregando NIS e MFSDA Junges, Andrizia de Freitas Pirazóis Reação de iodação NIS Reação de trifluormetilação MFSDA Bis(trifluormetil) Pyrazoles Iodination reaction Trifluoromethylation reaction Bis(trifluoromethyl) CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Síntese de 4,5-bis(trifluormetil)-1h-pirazóis através de reações eletrofílicas e nucleofílicas empregando NIS e MFSDA |
title_full |
Síntese de 4,5-bis(trifluormetil)-1h-pirazóis através de reações eletrofílicas e nucleofílicas empregando NIS e MFSDA |
title_fullStr |
Síntese de 4,5-bis(trifluormetil)-1h-pirazóis através de reações eletrofílicas e nucleofílicas empregando NIS e MFSDA |
title_full_unstemmed |
Síntese de 4,5-bis(trifluormetil)-1h-pirazóis através de reações eletrofílicas e nucleofílicas empregando NIS e MFSDA |
title_sort |
Síntese de 4,5-bis(trifluormetil)-1h-pirazóis através de reações eletrofílicas e nucleofílicas empregando NIS e MFSDA |
author |
Junges, Andrizia de Freitas |
author_facet |
Junges, Andrizia de Freitas |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Bonacorso, Helio Gauze |
dc.contributor.advisor1Lattes.fl_str_mv |
http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4788537E0 |
dc.contributor.referee1.fl_str_mv |
Fantinel, Leonardo |
dc.contributor.referee1Lattes.fl_str_mv |
http://lattes.cnpq.br/3934644027018397 |
dc.contributor.referee2.fl_str_mv |
Severo Filho, Wolmar Alípio |
dc.contributor.referee2Lattes.fl_str_mv |
http://lattes.cnpq.br/1999826579939679 |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/3902571039171981 |
dc.contributor.author.fl_str_mv |
Junges, Andrizia de Freitas |
contributor_str_mv |
Bonacorso, Helio Gauze Fantinel, Leonardo Severo Filho, Wolmar Alípio |
dc.subject.por.fl_str_mv |
Pirazóis Reação de iodação NIS Reação de trifluormetilação MFSDA Bis(trifluormetil) |
topic |
Pirazóis Reação de iodação NIS Reação de trifluormetilação MFSDA Bis(trifluormetil) Pyrazoles Iodination reaction Trifluoromethylation reaction Bis(trifluoromethyl) CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.eng.fl_str_mv |
Pyrazoles Iodination reaction Trifluoromethylation reaction Bis(trifluoromethyl) |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
This dissertation describes the development of an efficient methodology for the functionalization of position 4 of 3-alkyl(aryl)-1-aryl-5-trifluoromethyl-1H-pyrazoles systems by halogenation and subsequent reaction with trifluoromethylating reagent MFSDA, thus obtaining a series of six unpublished examples of 4-iodo-5-trifluoromethyl-1H -pyrazoles in addition to seven unpublished compounds of the 4,5- bis(trifluoromethyl)-1H-pyrazoles series. Initially eight examples of 1-aryl-3-alkyl (aryl) -5-trifluoromethyl-1H-pyrazoles where aryl = C6H5, 4-FC6H4, 4-ClC6H4 and alkyl = Me, c-Pr, i-Pr, n-Bu from the cyclocondensation reaction [3 + 2] between 4-alkyl (aryl) -4-alkoxy-1,1,1-trifluoro-3-alken-2-ones and arylhydrazines in yields of 91-94%. The synthesized starting materials were then subjected to CF3COOH -catalyzed electrophilic iodination using the N-iodosuccinimide (NIS) reagent resulting in a series of 4-iodo-5-trifluoromethyl-1H-pyrazoles in yields of 75-87%. Subsequently the optimization of the methodology of insertion of trifluoromethyl at the 4-position of the series of 4-iodo-5-trifluoromethyl-1H-pyrazoles through nucleophilic substitution using the MFSDA reagent was performed. For this, different copper salts and additives were tested, besides the study of the reaction in argon atmosphere. By optimizing the methodology it was possible to synthesize an unpublished series of 4,5-bis(trifluoromethyl)-1H-pyrazoles in yields of up to 79%. |
publishDate |
2019 |
dc.date.accessioned.fl_str_mv |
2019-06-05T20:50:02Z |
dc.date.available.fl_str_mv |
2019-06-05T20:50:02Z |
dc.date.issued.fl_str_mv |
2019-02-27 |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/masterThesis |
format |
masterThesis |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://repositorio.ufsm.br/handle/1/16761 |
url |
http://repositorio.ufsm.br/handle/1/16761 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.relation.cnpq.fl_str_mv |
100600000000 |
dc.relation.confidence.fl_str_mv |
600 |
dc.relation.authority.fl_str_mv |
06c852ad-d805-43c3-99d6-93a6a86f507c a4f46a68-70dc-4ccb-bd93-8795539cec67 b0e1e2a5-71c6-4a3f-9161-9fa6805b8b49 a07c475c-60f3-4ff9-bff8-2a4f54329a61 |
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 |
reponame:Biblioteca Digital de Teses e Dissertações do UFSM instname:Universidade Federal de Santa Maria (UFSM) instacron:UFSM |
instname_str |
Universidade Federal de Santa Maria (UFSM) |
instacron_str |
UFSM |
institution |
UFSM |
reponame_str |
Biblioteca Digital de Teses e Dissertações do UFSM |
collection |
Biblioteca Digital de Teses e Dissertações do UFSM |
bitstream.url.fl_str_mv |
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