Síntese de pirazóis e desenvolvimento de novos líquidos iônicos derivados de componentes farmacologicamente ativos
Ano de defesa: | 2011 |
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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
|
Programa de Pós-Graduação: |
Programa de Pós-Graduação em Química
|
Departamento: |
Química
|
País: |
BR
|
Palavras-chave em Português: | |
Palavras-chave em Inglês: | |
Área do conhecimento CNPq: | |
Link de acesso: | http://repositorio.ufsm.br/handle/1/4214 |
Resumo: | The synthesis of two series of N-substituted pyrazoles from the cyclocondensation reaction of β-enaminones ([R1C(O)C(R2)=CHN(Me2)], where R1 = Me, C6H5, 3-MeOC6H4, 4-Me-C6H4, 4-MeO-C6H4, 4-F-C6H4, 4-Cl-C6H4, 4-Br-C6H4, 4-O2N-C6H4, fur-2-il, thien-2-il; R2 = H, 2-MeO-C6H4) and 2-hydroxyethylhydrazine or 1-pentafluorophenylhydrazine was demonstrated. The reactions were performed in five ionic liquids ([BMIM][BF4], [BMIM][Br], [BMIM][OH], [HMIM][HSO4] e [BPy][BF4]) with different physical and chemical properties to establish the best reaction conditions. In addition, a Brönsted (HCl) and a Lewis catalyst (BF3●OEt2) and two molecular solvents (ethanol and water) were evaluated. The best ionic liquid found for all reactions was [BMIM][BF4]; molecular solvent ethanol for reaction with 2- hydroxyethylhydrazine; and water for reaction with 1-pentafluorophenylhydrazine. On the other hand, in the case of the reaction with 2-hydroxyethylhydrazine, BF3●OEt2 was found to be the best catalyst, while with 1- pentafluorophenylhydrazine, HCl, was found to be the best one, when comparing both reactions in [BMIM][BF4]. In general, the results showed it is advantage in yields and reaction time the use of ionic liquids in relation to molecular solvents. This work also shows the synthesis and characterization of a series of ionic liquids containing a pharmacological cation and/or anion. The new ionic liquids were synthesized from the metathesis reaction between the lidochaine, benzalkonium or didecyldimethylamonium salts, to furnish the cation part; and sodium diclofenac, sodium flurbiprofenate, sodium flufenamicate, sodium salicylate, sodium saccharinate and potassium acesulfamate, to furnish the anion part. The new ionic liquids were obtained in moderate to good yields (56-89%) and were identified and characterized through the NMR, DSC and TGA data. |
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2017-05-122017-05-122011-01-12MOREIRA, Dayse das Neves. Synthesis of pyrazoles and development of new ionic liquids derived from active pharmaceutical components. 2011. 214 f. Tese (Doutorado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2011.http://repositorio.ufsm.br/handle/1/4214The synthesis of two series of N-substituted pyrazoles from the cyclocondensation reaction of β-enaminones ([R1C(O)C(R2)=CHN(Me2)], where R1 = Me, C6H5, 3-MeOC6H4, 4-Me-C6H4, 4-MeO-C6H4, 4-F-C6H4, 4-Cl-C6H4, 4-Br-C6H4, 4-O2N-C6H4, fur-2-il, thien-2-il; R2 = H, 2-MeO-C6H4) and 2-hydroxyethylhydrazine or 1-pentafluorophenylhydrazine was demonstrated. The reactions were performed in five ionic liquids ([BMIM][BF4], [BMIM][Br], [BMIM][OH], [HMIM][HSO4] e [BPy][BF4]) with different physical and chemical properties to establish the best reaction conditions. In addition, a Brönsted (HCl) and a Lewis catalyst (BF3●OEt2) and two molecular solvents (ethanol and water) were evaluated. The best ionic liquid found for all reactions was [BMIM][BF4]; molecular solvent ethanol for reaction with 2- hydroxyethylhydrazine; and water for reaction with 1-pentafluorophenylhydrazine. On the other hand, in the case of the reaction with 2-hydroxyethylhydrazine, BF3●OEt2 was found to be the best catalyst, while with 1- pentafluorophenylhydrazine, HCl, was found to be the best one, when comparing both reactions in [BMIM][BF4]. In general, the results showed it is advantage in yields and reaction time the use of ionic liquids in relation to molecular solvents. This work also shows the synthesis and characterization of a series of ionic liquids containing a pharmacological cation and/or anion. The new ionic liquids were synthesized from the metathesis reaction between the lidochaine, benzalkonium or didecyldimethylamonium salts, to furnish the cation part; and sodium diclofenac, sodium flurbiprofenate, sodium flufenamicate, sodium salicylate, sodium saccharinate and potassium acesulfamate, to furnish the anion part. The new ionic liquids were obtained in moderate to good yields (56-89%) and were identified and characterized through the NMR, DSC and TGA data.Este trabalho descreve a síntese de duas séries de pirazóis N-substituídos, a partir da reação de ciclocondensação entre β-enaminonas ([R1C(O)C(R2)=CHN(Me2)], onde R1 = Me, C6H5, 3-MeO-C6H4, 4-Me-C6H4, 4-MeO-C6H4, 4-F-C6H4, 4-Cl-C6H4, 4- Br-C6H4, 4-O2N-C6H4, fur-2-il, tien-2-il; R2 = H, 2-MeO-C6H4) e 2-hidroxietilidrazina ou 1-pentafluorfenilidrazina. As reações foram realizadas em diferentes líquidos iônicos ([BMIM][BF4], [BMIM][Br], [BMIM][OH], [HMIM][HSO4] e [BPy][BF4]) com propriedades físicas e químicas diferentes a fim de estabelecer as melhores condições para a obtenção dos 1-hidroxietilpirazóis e dos 1-pentafluorfenilpirazóis. Além disso, também foram avaliados diferentes catalisadores (HCl e BF3●OEt2) e dois solventes moleculares (etanol e água). Em ambos os casos, o líquido iônico [BMIM][BF4] apresentou os melhores resultados. No entanto, quanto ao catalisador avaliado, foi verificado um comportamento distinto. A reação entre hidroxietilidrazina e enaminonas [BMIM][BF4] foi melhor quando BF3●OEt2 foi utilizado como catalisador, enquanto que para a reação da pentafluorfenilidrazina, HCl se mostrou mais adequado. Além disso, o melhor solvente molecular encontrado para a reação com a 2-hidroxietilidrazina foi o etanol enquanto que no caso da 1- pentafluorfenilidrazina, a água apresentou resultados superiores em termos de tempo reacional e rendimento. Através dos resultados obtidos foi possível observar que a utilização de líquidos iônicos apresenta vantagens em relação a utilização de solventes moleculares. Nesta tese, também foram sintetizadas series de líquidos iônicos contendo componentes farmacologicamente ativos, tanto no cátion quanto no ânion do referido composto. Os novos líquidos iônicos duais foram sintetizados através de uma reação de metátese entre sais de lidocaína, benzalcônio ou didecildimetilamônio, os quais forneceram a parte catiônica, com diferentes sais como, diclofenaco de sódio, flurbiprofenato de sódio, flufenamicato de sódio, salicilato de sódio, sacarinato de sódio e acesulfamato de potássio. Esses compostos foram obtidos em rendimentos moderados a bons (56-89%), e foram identificados e caraterizados através de dados de RMN, DSC e TGA.Coordenação de Aperfeiçoamento de Pessoal de Nível Superiorapplication/pdfporUniversidade Federal de Santa MariaPrograma de Pós-Graduação em QuímicaUFSMBRQuímicaβ-enaminonas2-hidroxietilidrazina1-pentafluorfenilidrazinaPirazóisReações de ciclocondensaçãoLíquidos iônicosβ-enaminones2-hydroxyethylhydrazine1-pentafluorophenylhydrazinePyrazolesCyclocondensation reactionsIonic liquidsCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese de pirazóis e desenvolvimento de novos líquidos iônicos derivados de componentes farmacologicamente ativosSynthesis of pyrazoles and development of new ionic liquids derived from active pharmaceutical componentsinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisMartins, Marcos Antonio Pintohttp://lattes.cnpq.br/6457412713967642Bonacorso, Helio Gauzehttp://lattes.cnpq.br/7275608974248322Zanatta, Nilohttp://lattes.cnpq.br/0719465062354576Siqueira, Geonir Machadohttp://lattes.cnpq.br/3245577879591660D'Oca, Marcelo Gonçalves Monteshttp://lattes.cnpq.br/6909434144537391http://lattes.cnpq.br/0161193498921169Moreira, Dayse das Neves100600000000400300300300300300300c28419d9-6027-4f9c-acd2-76e8067a85d1edd78206-9c43-48f2-a723-24bc697e581cdbcce58b-96b0-4f45-a78d-ca6f339e038d2f7bd6ce-78fa-4968-ac66-2d1407e90f603b4bc502-9bc1-4539-9874-d13383d8e3dca10ffa2f-581f-4ead-8022-d48a8364647finfo:eu-repo/semantics/openAccessreponame:Manancial - Repositório Digital da UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALMOREIRA, DAYSE DAS NEVES.pdfapplication/pdf7309882http://repositorio.ufsm.br/bitstream/1/4214/1/MOREIRA%2c%20DAYSE%20DAS%20NEVES.pdf8a46b9b079d8e68e8793f0cd37b38bf4MD51TEXTMOREIRA, DAYSE DAS NEVES.pdf.txtMOREIRA, DAYSE DAS NEVES.pdf.txtExtracted texttext/plain186127http://repositorio.ufsm.br/bitstream/1/4214/2/MOREIRA%2c%20DAYSE%20DAS%20NEVES.pdf.txt94f4b691a0cf4e3361f8ce4c0f3327f7MD52THUMBNAILMOREIRA, DAYSE DAS NEVES.pdf.jpgMOREIRA, DAYSE DAS NEVES.pdf.jpgIM Thumbnailimage/jpeg6181http://repositorio.ufsm.br/bitstream/1/4214/3/MOREIRA%2c%20DAYSE%20DAS%20NEVES.pdf.jpg6b3fe003a3abec187a1cce77baef57e6MD531/42142023-06-15 12:54:31.186oai:repositorio.ufsm.br:1/4214Repositório Institucionalhttp://repositorio.ufsm.br/PUBhttp://repositorio.ufsm.br/oai/requestopendoar:39132023-06-15T15:54:31Manancial - Repositório Digital da UFSM - Universidade Federal de Santa Maria (UFSM)false |
dc.title.por.fl_str_mv |
Síntese de pirazóis e desenvolvimento de novos líquidos iônicos derivados de componentes farmacologicamente ativos |
dc.title.alternative.eng.fl_str_mv |
Synthesis of pyrazoles and development of new ionic liquids derived from active pharmaceutical components |
title |
Síntese de pirazóis e desenvolvimento de novos líquidos iônicos derivados de componentes farmacologicamente ativos |
spellingShingle |
Síntese de pirazóis e desenvolvimento de novos líquidos iônicos derivados de componentes farmacologicamente ativos Moreira, Dayse das Neves β-enaminonas 2-hidroxietilidrazina 1-pentafluorfenilidrazina Pirazóis Reações de ciclocondensação Líquidos iônicos β-enaminones 2-hydroxyethylhydrazine 1-pentafluorophenylhydrazine Pyrazoles Cyclocondensation reactions Ionic liquids CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Síntese de pirazóis e desenvolvimento de novos líquidos iônicos derivados de componentes farmacologicamente ativos |
title_full |
Síntese de pirazóis e desenvolvimento de novos líquidos iônicos derivados de componentes farmacologicamente ativos |
title_fullStr |
Síntese de pirazóis e desenvolvimento de novos líquidos iônicos derivados de componentes farmacologicamente ativos |
title_full_unstemmed |
Síntese de pirazóis e desenvolvimento de novos líquidos iônicos derivados de componentes farmacologicamente ativos |
title_sort |
Síntese de pirazóis e desenvolvimento de novos líquidos iônicos derivados de componentes farmacologicamente ativos |
author |
Moreira, Dayse das Neves |
author_facet |
Moreira, Dayse das Neves |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Martins, Marcos Antonio Pinto |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/6457412713967642 |
dc.contributor.referee1.fl_str_mv |
Bonacorso, Helio Gauze |
dc.contributor.referee1Lattes.fl_str_mv |
http://lattes.cnpq.br/7275608974248322 |
dc.contributor.referee2.fl_str_mv |
Zanatta, Nilo |
dc.contributor.referee2Lattes.fl_str_mv |
http://lattes.cnpq.br/0719465062354576 |
dc.contributor.referee3.fl_str_mv |
Siqueira, Geonir Machado |
dc.contributor.referee3Lattes.fl_str_mv |
http://lattes.cnpq.br/3245577879591660 |
dc.contributor.referee4.fl_str_mv |
D'Oca, Marcelo Gonçalves Montes |
dc.contributor.referee4Lattes.fl_str_mv |
http://lattes.cnpq.br/6909434144537391 |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/0161193498921169 |
dc.contributor.author.fl_str_mv |
Moreira, Dayse das Neves |
contributor_str_mv |
Martins, Marcos Antonio Pinto Bonacorso, Helio Gauze Zanatta, Nilo Siqueira, Geonir Machado D'Oca, Marcelo Gonçalves Montes |
dc.subject.por.fl_str_mv |
β-enaminonas 2-hidroxietilidrazina 1-pentafluorfenilidrazina Pirazóis Reações de ciclocondensação Líquidos iônicos |
topic |
β-enaminonas 2-hidroxietilidrazina 1-pentafluorfenilidrazina Pirazóis Reações de ciclocondensação Líquidos iônicos β-enaminones 2-hydroxyethylhydrazine 1-pentafluorophenylhydrazine Pyrazoles Cyclocondensation reactions Ionic liquids CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.eng.fl_str_mv |
β-enaminones 2-hydroxyethylhydrazine 1-pentafluorophenylhydrazine Pyrazoles Cyclocondensation reactions Ionic liquids |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
The synthesis of two series of N-substituted pyrazoles from the cyclocondensation reaction of β-enaminones ([R1C(O)C(R2)=CHN(Me2)], where R1 = Me, C6H5, 3-MeOC6H4, 4-Me-C6H4, 4-MeO-C6H4, 4-F-C6H4, 4-Cl-C6H4, 4-Br-C6H4, 4-O2N-C6H4, fur-2-il, thien-2-il; R2 = H, 2-MeO-C6H4) and 2-hydroxyethylhydrazine or 1-pentafluorophenylhydrazine was demonstrated. The reactions were performed in five ionic liquids ([BMIM][BF4], [BMIM][Br], [BMIM][OH], [HMIM][HSO4] e [BPy][BF4]) with different physical and chemical properties to establish the best reaction conditions. In addition, a Brönsted (HCl) and a Lewis catalyst (BF3●OEt2) and two molecular solvents (ethanol and water) were evaluated. The best ionic liquid found for all reactions was [BMIM][BF4]; molecular solvent ethanol for reaction with 2- hydroxyethylhydrazine; and water for reaction with 1-pentafluorophenylhydrazine. On the other hand, in the case of the reaction with 2-hydroxyethylhydrazine, BF3●OEt2 was found to be the best catalyst, while with 1- pentafluorophenylhydrazine, HCl, was found to be the best one, when comparing both reactions in [BMIM][BF4]. In general, the results showed it is advantage in yields and reaction time the use of ionic liquids in relation to molecular solvents. This work also shows the synthesis and characterization of a series of ionic liquids containing a pharmacological cation and/or anion. The new ionic liquids were synthesized from the metathesis reaction between the lidochaine, benzalkonium or didecyldimethylamonium salts, to furnish the cation part; and sodium diclofenac, sodium flurbiprofenate, sodium flufenamicate, sodium salicylate, sodium saccharinate and potassium acesulfamate, to furnish the anion part. The new ionic liquids were obtained in moderate to good yields (56-89%) and were identified and characterized through the NMR, DSC and TGA data. |
publishDate |
2011 |
dc.date.issued.fl_str_mv |
2011-01-12 |
dc.date.accessioned.fl_str_mv |
2017-05-12 |
dc.date.available.fl_str_mv |
2017-05-12 |
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.citation.fl_str_mv |
MOREIRA, Dayse das Neves. Synthesis of pyrazoles and development of new ionic liquids derived from active pharmaceutical components. 2011. 214 f. Tese (Doutorado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2011. |
dc.identifier.uri.fl_str_mv |
http://repositorio.ufsm.br/handle/1/4214 |
identifier_str_mv |
MOREIRA, Dayse das Neves. Synthesis of pyrazoles and development of new ionic liquids derived from active pharmaceutical components. 2011. 214 f. Tese (Doutorado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2011. |
url |
http://repositorio.ufsm.br/handle/1/4214 |
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por |
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100600000000 |
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Universidade Federal de Santa Maria |
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Programa de Pós-Graduação em Química |
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UFSM |
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Química |
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Universidade Federal de Santa Maria |
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