Síntese de 1,4-diazaciclo-2-ilidenos N-pirrolil/furanil substituídos
Ano de defesa: | 2018 |
---|---|
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: | |
Área do conhecimento CNPq: | |
Link de acesso: | http://repositorio.ufsm.br/handle/1/16096 |
Resumo: | This work presents the synthesis of piperazines, 1,4-diazepanes and 1,4-diazocanes pyrrolyl or furanyl-functionalized at the N4 position of the diazacycle. In this manner, four series of compounds were prepared, with a larger emphasis on seven-membered heterocycles (1,4- diazepanes), given the pronounced biological and pharmacological that this class of compounds usually present. The one-pot methodology developed for this work consists in the reaction of 5-bromo-1,1,1-trifluoro-4-methoxypent-3-en-2-one (enone) with terminal aliphatic diamines (1,2-diaminethane, 1,3-diaminepropane and 1,4-diaminebutane, in a molar ratio of 2:1), resulting in the addition of one molecule of diamine at the 4 position of two molecules of the enone. The dimer γ-bromo-β-aminovinyl trifluoromethyl ketone formed presented itself to be extremely reactive and the vinylic nitrogen being was able to attack the other CH2Br center. At this point, a second nitrogen nucleophile (aliphatic and aromatic amines) was added to promote the cyclocondensation reaction and prepare trifluoromethyl pyrroles connected directly at the 4 position of the heterocycle formed by the dimer. The final products were obtained with 40 – 71% overall yield. During the optimization of reaction conditions, it was observed the formation of a byproduct, that was identified as being the corresponding 1,4-diazacycle with a trifluoromethylated furan at N4 position (instead of the pyrrole), which is resulting of the cyclocondensation reaction of the enaminone in basic media. In this form, conditions for the synthesis of the compounds bearing a furan were investigated. Since the amine acted both as base and nucleophile in the preparation of the pyrroles derivatives, the reaction to prepare the furan was carried out using a non-nucleophilic base (Na2CO3) and the final compounds were obtained in 91 – 96% overall yields. The products obtained in this work were fully characterized by nuclear magnetic resonance of hydrogen and carbon 13, low-resolution mass spectrometry, elemental analysis, melting points and single crystal X-ray diffraction. |
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2019-04-08T15:16:19Z2019-04-08T15:16:19Z2018-08-06http://repositorio.ufsm.br/handle/1/16096This work presents the synthesis of piperazines, 1,4-diazepanes and 1,4-diazocanes pyrrolyl or furanyl-functionalized at the N4 position of the diazacycle. In this manner, four series of compounds were prepared, with a larger emphasis on seven-membered heterocycles (1,4- diazepanes), given the pronounced biological and pharmacological that this class of compounds usually present. The one-pot methodology developed for this work consists in the reaction of 5-bromo-1,1,1-trifluoro-4-methoxypent-3-en-2-one (enone) with terminal aliphatic diamines (1,2-diaminethane, 1,3-diaminepropane and 1,4-diaminebutane, in a molar ratio of 2:1), resulting in the addition of one molecule of diamine at the 4 position of two molecules of the enone. The dimer γ-bromo-β-aminovinyl trifluoromethyl ketone formed presented itself to be extremely reactive and the vinylic nitrogen being was able to attack the other CH2Br center. At this point, a second nitrogen nucleophile (aliphatic and aromatic amines) was added to promote the cyclocondensation reaction and prepare trifluoromethyl pyrroles connected directly at the 4 position of the heterocycle formed by the dimer. The final products were obtained with 40 – 71% overall yield. During the optimization of reaction conditions, it was observed the formation of a byproduct, that was identified as being the corresponding 1,4-diazacycle with a trifluoromethylated furan at N4 position (instead of the pyrrole), which is resulting of the cyclocondensation reaction of the enaminone in basic media. In this form, conditions for the synthesis of the compounds bearing a furan were investigated. Since the amine acted both as base and nucleophile in the preparation of the pyrroles derivatives, the reaction to prepare the furan was carried out using a non-nucleophilic base (Na2CO3) and the final compounds were obtained in 91 – 96% overall yields. The products obtained in this work were fully characterized by nuclear magnetic resonance of hydrogen and carbon 13, low-resolution mass spectrometry, elemental analysis, melting points and single crystal X-ray diffraction.A presente dissertação apresenta a síntese de piperazinas, 1,4-diazepanos e 1,4-diazocanos pirrolil ou furanil-funcionalizados na posição N4 do diazaciclo. Desta forma, foram preparadas quatro séries de compostos, com ênfase maior nos heterociclos de sete membros (1,4- diazepanos), visto a pronunciada atividade biológica e farmacológica que compostos estruturalmente relacionados apresentam. A metodologia one-pot desenvolvida para este trabalho consiste na reação de 5-bromo-1,1,1-trifluor-4-metoxipent-3-en-2-ona (enona) com diaminas alifáticas terminais (1,2-diaminoetano, 1,3-diaminopropano e 1,4-diaminobutano, em uma relação 2:1), ocorrendo a adição de uma molécula de diamina na posição β de duas moléculas da enona. O dímero γ-bromo-β-aminovinil trifluormetil cetona formado se mostrou extremamente reativo, sendo que o nitrogênio vinílico se mostrou nucleofílico para atacar o outro centro CH2Br. Neste ponto, foi adicionado um segundo nucleófilo de nitrogênio (aminas alifáticas e arílicas) para promover a reação de ciclocondensação e preparar os pirróis trifluormetilados conectados diretamente à posição 4 do heterociclo formado pelo dímero. Os produtos finais foram obtidos com rendimentos de 40 – 71%. Durante o processo de otimização das condições reacionais foi observada a formação de um subproduto, que foi identificado como sendo o correspondente 1,4-diazaciclo com um furano trifluormetilado na posição N4 (ao invés do pirrol), que é resultante da ciclocondensação da enaminona em meio básico. Desta maneira, foram investigadas condições para a síntese dos compostos contendo os furanos trifluormetilados. Uma vez que a amina atuou como base e nucleófilo na formação dos pirróis, a reação do furano foi feita utilizando uma base não-nucleofílica (Na2CO3), obtendo os compostos finais com rendimentos de 91 – 96%. Os produtos obtidos neste trabalho foram caracterizados por ressonância magnética nuclear de hidrogênio e carbono 13, espectrometria de massas de baixa resolução, análise elementar, ponto de fusão e difração de raios-X de monocristal.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/openAccess1,4-diazaciclo-2-ilidenosN-pirrolil/furanilCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese de 1,4-diazaciclo-2-ilidenos N-pirrolil/furanil substituídosSynthesis of 1,4-diazacyclo-2-ylidenes N-pyrrolyl/furanyl substitutedinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisZanatta, Nilohttp://lattes.cnpq.br/0719465062354576Lüdtke, Diogo Seiberthttp://lattes.cnpq.br/0831151849844477Zeni, Gilson Rogériohttp://lattes.cnpq.br/2355575631197937http://lattes.cnpq.br/7341503512916041Mittersteiner, Mateus100600000000600233dc1de-ab03-4f57-9b85-e40dc01a2d4fc9c2a799-83c4-429c-8887-b1607dbb636da2ac0343-9b3c-4004-96b1-41b889220f939886a90a-985e-4537-825b-61dc895c650areponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALDIS_PPGQUIMICA_2018_MITTERSTEINER_MATEUS.pdfDIS_PPGQUIMICA_2018_MITTERSTEINER_MATEUS.pdfDissertação de Mestradoapplication/pdf4559803http://repositorio.ufsm.br/bitstream/1/16096/1/DIS_PPGQUIMICA_2018_MITTERSTEINER_MATEUS.pdf3bacf93d94d7f102b1d80ad5d17aa3a9MD51CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; 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dc.title.por.fl_str_mv |
Síntese de 1,4-diazaciclo-2-ilidenos N-pirrolil/furanil substituídos |
dc.title.alternative.eng.fl_str_mv |
Synthesis of 1,4-diazacyclo-2-ylidenes N-pyrrolyl/furanyl substituted |
title |
Síntese de 1,4-diazaciclo-2-ilidenos N-pirrolil/furanil substituídos |
spellingShingle |
Síntese de 1,4-diazaciclo-2-ilidenos N-pirrolil/furanil substituídos Mittersteiner, Mateus 1,4-diazaciclo-2-ilidenos N-pirrolil/furanil CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Síntese de 1,4-diazaciclo-2-ilidenos N-pirrolil/furanil substituídos |
title_full |
Síntese de 1,4-diazaciclo-2-ilidenos N-pirrolil/furanil substituídos |
title_fullStr |
Síntese de 1,4-diazaciclo-2-ilidenos N-pirrolil/furanil substituídos |
title_full_unstemmed |
Síntese de 1,4-diazaciclo-2-ilidenos N-pirrolil/furanil substituídos |
title_sort |
Síntese de 1,4-diazaciclo-2-ilidenos N-pirrolil/furanil substituídos |
author |
Mittersteiner, Mateus |
author_facet |
Mittersteiner, Mateus |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Zanatta, Nilo |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/0719465062354576 |
dc.contributor.referee1.fl_str_mv |
Lüdtke, Diogo Seibert |
dc.contributor.referee1Lattes.fl_str_mv |
http://lattes.cnpq.br/0831151849844477 |
dc.contributor.referee2.fl_str_mv |
Zeni, Gilson Rogério |
dc.contributor.referee2Lattes.fl_str_mv |
http://lattes.cnpq.br/2355575631197937 |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/7341503512916041 |
dc.contributor.author.fl_str_mv |
Mittersteiner, Mateus |
contributor_str_mv |
Zanatta, Nilo Lüdtke, Diogo Seibert Zeni, Gilson Rogério |
dc.subject.por.fl_str_mv |
1,4-diazaciclo-2-ilidenos N-pirrolil/furanil |
topic |
1,4-diazaciclo-2-ilidenos N-pirrolil/furanil CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
This work presents the synthesis of piperazines, 1,4-diazepanes and 1,4-diazocanes pyrrolyl or furanyl-functionalized at the N4 position of the diazacycle. In this manner, four series of compounds were prepared, with a larger emphasis on seven-membered heterocycles (1,4- diazepanes), given the pronounced biological and pharmacological that this class of compounds usually present. The one-pot methodology developed for this work consists in the reaction of 5-bromo-1,1,1-trifluoro-4-methoxypent-3-en-2-one (enone) with terminal aliphatic diamines (1,2-diaminethane, 1,3-diaminepropane and 1,4-diaminebutane, in a molar ratio of 2:1), resulting in the addition of one molecule of diamine at the 4 position of two molecules of the enone. The dimer γ-bromo-β-aminovinyl trifluoromethyl ketone formed presented itself to be extremely reactive and the vinylic nitrogen being was able to attack the other CH2Br center. At this point, a second nitrogen nucleophile (aliphatic and aromatic amines) was added to promote the cyclocondensation reaction and prepare trifluoromethyl pyrroles connected directly at the 4 position of the heterocycle formed by the dimer. The final products were obtained with 40 – 71% overall yield. During the optimization of reaction conditions, it was observed the formation of a byproduct, that was identified as being the corresponding 1,4-diazacycle with a trifluoromethylated furan at N4 position (instead of the pyrrole), which is resulting of the cyclocondensation reaction of the enaminone in basic media. In this form, conditions for the synthesis of the compounds bearing a furan were investigated. Since the amine acted both as base and nucleophile in the preparation of the pyrroles derivatives, the reaction to prepare the furan was carried out using a non-nucleophilic base (Na2CO3) and the final compounds were obtained in 91 – 96% overall yields. The products obtained in this work were fully characterized by nuclear magnetic resonance of hydrogen and carbon 13, low-resolution mass spectrometry, elemental analysis, melting points and single crystal X-ray diffraction. |
publishDate |
2018 |
dc.date.issued.fl_str_mv |
2018-08-06 |
dc.date.accessioned.fl_str_mv |
2019-04-08T15:16:19Z |
dc.date.available.fl_str_mv |
2019-04-08T15:16:19Z |
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/1/16096 |
url |
http://repositorio.ufsm.br/handle/1/16096 |
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 |
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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 |
reponame:Biblioteca Digital de Teses e Dissertações do UFSM instname:Universidade Federal de Santa Maria (UFSM) instacron:UFSM |
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Biblioteca Digital de Teses e Dissertações do UFSM |
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