Síntese de 4-trifluormetil-5-(propan-1-ol-3-il)-1H-piridin-2-iminas N-substituídas
Ano de defesa: | 2013 |
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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
|
Programa de Pós-Graduação: |
Programa de Pós-Graduação em Química
|
Departamento: |
Química
|
País: |
BR
|
Palavras-chave em Português: | |
Área do conhecimento CNPq: | |
Link de acesso: | http://repositorio.ufsm.br/handle/1/10540 |
Resumo: | This work presents a simple and accessible synthetic route for the preparation of a series, of nineteen new N-substituted 4-trifluormethyl-5- (propan-1-ol-3-yl)-pyridin-2-(1H)-imines, obtained from the reaction between 3- (3,4-dihydro-2H-pyran-5-yl)-4,4,4-trifluorobut-2-enenitrile with the following amines: methylamine, ethylamine, propylamine, iso-propylamine, butylamine, sec-butylamine, benzylamine, phenethylamine, 2-methoxy-phenethylamine, 4- methoxy-phenethylamine, 3,4-methoxy-phenethylamine, 4-fluorophenethylamine, 2-chloro-phenethylamine, 3-chloro-phenethylamine, 4-chlorophenethylamine, 2-(1-cyclohexenyl)-ethylamine, 2-N-morpholyl-ethylamine, N,N-dimethyl-ethyl-1,2-diamine e N,N-diethyl-ethyl-1,2-diamine. The 2-pyridinimines were synthetized through a solvent free methodology and in a short reaction time. The purification step was performed with liquidliquid extractions. After evaporation of the solvent, the product was washed with hot hexane to remove any trace of residual amine. The products were obtained with yield between 29-82%. The 2-pyridinimines obtained in this work were characterized by 1H and 13C NMR, 2D NMR, Mass Spectrometry, and Infrared Spectroscopy and their purity confirmed by Elemental Analysis and/or High Resolution Mass Spectrometry. |
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2014-06-122014-06-122013-03-08MARANGONI, Mário André. Synthesis of N-substituted 4-trifluoromethyl-5-(propan-1-ol-3-yl)-pyridin-2-(1H)-imines". 2013. 137 f. Dissertação (Mestrado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2013.http://repositorio.ufsm.br/handle/1/10540This work presents a simple and accessible synthetic route for the preparation of a series, of nineteen new N-substituted 4-trifluormethyl-5- (propan-1-ol-3-yl)-pyridin-2-(1H)-imines, obtained from the reaction between 3- (3,4-dihydro-2H-pyran-5-yl)-4,4,4-trifluorobut-2-enenitrile with the following amines: methylamine, ethylamine, propylamine, iso-propylamine, butylamine, sec-butylamine, benzylamine, phenethylamine, 2-methoxy-phenethylamine, 4- methoxy-phenethylamine, 3,4-methoxy-phenethylamine, 4-fluorophenethylamine, 2-chloro-phenethylamine, 3-chloro-phenethylamine, 4-chlorophenethylamine, 2-(1-cyclohexenyl)-ethylamine, 2-N-morpholyl-ethylamine, N,N-dimethyl-ethyl-1,2-diamine e N,N-diethyl-ethyl-1,2-diamine. The 2-pyridinimines were synthetized through a solvent free methodology and in a short reaction time. The purification step was performed with liquidliquid extractions. After evaporation of the solvent, the product was washed with hot hexane to remove any trace of residual amine. The products were obtained with yield between 29-82%. The 2-pyridinimines obtained in this work were characterized by 1H and 13C NMR, 2D NMR, Mass Spectrometry, and Infrared Spectroscopy and their purity confirmed by Elemental Analysis and/or High Resolution Mass Spectrometry.Este trabalho apresenta uma rota sintética simples e acessível para a preparação de uma série inédita com dezenove compostos 4-trifluormetil-5- (propan-1-ol-3-il)-1H-piridin-2-iminas N-substituídas, a partir da reação entre o 3-(3,4-diidro-2H-piran-5-il)-4,4,4-trifluorbut-2-enonitrila com as seguintes aminas primárias: metilamina, etilamina, propilamina, iso-propilamina, butilamina, sec-butilamina, benzilamina, fenetilamina, 2-metóxi-fenetilamina, 4- metóxi-fenetilamina, 3,4-metóxi-fenetilamina, 4-fluor-fenetilamina, 2-clorofenetilamina, 3-cloro-fenetilamina, 4-cloro-fenetilamina, 2-(1-cicloexenil)- etilamina, 2-N-morfolil-etilamina, N,N-dimetil-etil-1,2-diamina e N,N-dietil-etil- 1,2-diamina. A síntese destes compostos foi realizada através da utilização de uma metodologia livre do uso de solventes em curtos tempos reacionais. A etapa de purificação foi realizada com extrações líquido-líquido. Posteriormente, o produto proveniente da extração, foi lavado com hexano a quente, a fim de remover algum traço de amina residual. Os rendimentos obtidos dos compostos foram em torno de 29-82%. As 2-piridiniminas obtidas neste trabalho foram caracterizadas por Ressonância Magnética Nuclear de Hidrogênio, Ressonância Magnética Nuclear de Carbono-13, Espectrometria de Massas e Espectroscopia de Infravermelho, seus graus de pureza comprovadas via Análise Elementar e/ou Espectrometria de Massas de Alta Resolução.Coordenação de Aperfeiçoamento de Pessoal de Nível Superiorapplication/pdfporUniversidade Federal de Santa MariaPrograma de Pós-Graduação em QuímicaUFSMBRQuímicaQuímica2-piridiniminasSolvent free1-ciano-buta-1,3-dienosCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese de 4-trifluormetil-5-(propan-1-ol-3-il)-1H-piridin-2-iminas N-substituídasSynthesis of N-substituted 4-trifluoromethyl-5-(propan-1-ol-3-yl)-pyridin-2-(1H)-imines"info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisZanatta, Nilohttp://lattes.cnpq.br/0719465062354576Fantinel, Leonardohttp://lattes.cnpq.br/3934644027018397http://lattes.cnpq.br/4272189612869632Marangoni, Mário André100600000000400500300300233dc1de-ab03-4f57-9b85-e40dc01a2d4f9ad81139-6ca6-40d5-a3d6-5ba26af2fadcb0e1e2a5-71c6-4a3f-9161-9fa6805b8b49info:eu-repo/semantics/openAccessreponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALMARANGONI, MARIO ANDRE.pdfapplication/pdf9171946http://repositorio.ufsm.br/bitstream/1/10540/1/MARANGONI%2c%20MARIO%20ANDRE.pdf211b0c974cddcef8fb9adc1c0ca5e988MD51TEXTMARANGONI, MARIO ANDRE.pdf.txtMARANGONI, MARIO ANDRE.pdf.txtExtracted texttext/plain113028http://repositorio.ufsm.br/bitstream/1/10540/2/MARANGONI%2c%20MARIO%20ANDRE.pdf.txtedda135451085c23a9054b45f936a08bMD52THUMBNAILMARANGONI, MARIO ANDRE.pdf.jpgMARANGONI, MARIO ANDRE.pdf.jpgIM Thumbnailimage/jpeg5937http://repositorio.ufsm.br/bitstream/1/10540/3/MARANGONI%2c%20MARIO%20ANDRE.pdf.jpgc00c760c4f5b7bceffd554829f478b3fMD531/105402023-06-12 16:20:28.875oai:repositorio.ufsm.br:1/10540Biblioteca Digital de Teses e Dissertaçõeshttps://repositorio.ufsm.br/ONGhttps://repositorio.ufsm.br/oai/requestatendimento.sib@ufsm.br||tedebc@gmail.comopendoar:2023-06-12T19:20:28Biblioteca Digital de Teses e Dissertações do UFSM - Universidade Federal de Santa Maria (UFSM)false |
dc.title.por.fl_str_mv |
Síntese de 4-trifluormetil-5-(propan-1-ol-3-il)-1H-piridin-2-iminas N-substituídas |
dc.title.alternative.eng.fl_str_mv |
Synthesis of N-substituted 4-trifluoromethyl-5-(propan-1-ol-3-yl)-pyridin-2-(1H)-imines" |
title |
Síntese de 4-trifluormetil-5-(propan-1-ol-3-il)-1H-piridin-2-iminas N-substituídas |
spellingShingle |
Síntese de 4-trifluormetil-5-(propan-1-ol-3-il)-1H-piridin-2-iminas N-substituídas Marangoni, Mário André Química 2-piridiniminas Solvent free 1-ciano-buta-1,3-dienos CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Síntese de 4-trifluormetil-5-(propan-1-ol-3-il)-1H-piridin-2-iminas N-substituídas |
title_full |
Síntese de 4-trifluormetil-5-(propan-1-ol-3-il)-1H-piridin-2-iminas N-substituídas |
title_fullStr |
Síntese de 4-trifluormetil-5-(propan-1-ol-3-il)-1H-piridin-2-iminas N-substituídas |
title_full_unstemmed |
Síntese de 4-trifluormetil-5-(propan-1-ol-3-il)-1H-piridin-2-iminas N-substituídas |
title_sort |
Síntese de 4-trifluormetil-5-(propan-1-ol-3-il)-1H-piridin-2-iminas N-substituídas |
author |
Marangoni, Mário André |
author_facet |
Marangoni, Mário André |
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 |
Fantinel, Leonardo |
dc.contributor.referee1Lattes.fl_str_mv |
http://lattes.cnpq.br/3934644027018397 |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/4272189612869632 |
dc.contributor.author.fl_str_mv |
Marangoni, Mário André |
contributor_str_mv |
Zanatta, Nilo Fantinel, Leonardo |
dc.subject.por.fl_str_mv |
Química 2-piridiniminas Solvent free 1-ciano-buta-1,3-dienos |
topic |
Química 2-piridiniminas Solvent free 1-ciano-buta-1,3-dienos CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
This work presents a simple and accessible synthetic route for the preparation of a series, of nineteen new N-substituted 4-trifluormethyl-5- (propan-1-ol-3-yl)-pyridin-2-(1H)-imines, obtained from the reaction between 3- (3,4-dihydro-2H-pyran-5-yl)-4,4,4-trifluorobut-2-enenitrile with the following amines: methylamine, ethylamine, propylamine, iso-propylamine, butylamine, sec-butylamine, benzylamine, phenethylamine, 2-methoxy-phenethylamine, 4- methoxy-phenethylamine, 3,4-methoxy-phenethylamine, 4-fluorophenethylamine, 2-chloro-phenethylamine, 3-chloro-phenethylamine, 4-chlorophenethylamine, 2-(1-cyclohexenyl)-ethylamine, 2-N-morpholyl-ethylamine, N,N-dimethyl-ethyl-1,2-diamine e N,N-diethyl-ethyl-1,2-diamine. The 2-pyridinimines were synthetized through a solvent free methodology and in a short reaction time. The purification step was performed with liquidliquid extractions. After evaporation of the solvent, the product was washed with hot hexane to remove any trace of residual amine. The products were obtained with yield between 29-82%. The 2-pyridinimines obtained in this work were characterized by 1H and 13C NMR, 2D NMR, Mass Spectrometry, and Infrared Spectroscopy and their purity confirmed by Elemental Analysis and/or High Resolution Mass Spectrometry. |
publishDate |
2013 |
dc.date.issued.fl_str_mv |
2013-03-08 |
dc.date.accessioned.fl_str_mv |
2014-06-12 |
dc.date.available.fl_str_mv |
2014-06-12 |
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.citation.fl_str_mv |
MARANGONI, Mário André. Synthesis of N-substituted 4-trifluoromethyl-5-(propan-1-ol-3-yl)-pyridin-2-(1H)-imines". 2013. 137 f. Dissertação (Mestrado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2013. |
dc.identifier.uri.fl_str_mv |
http://repositorio.ufsm.br/handle/1/10540 |
identifier_str_mv |
MARANGONI, Mário André. Synthesis of N-substituted 4-trifluoromethyl-5-(propan-1-ol-3-yl)-pyridin-2-(1H)-imines". 2013. 137 f. Dissertação (Mestrado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2013. |
url |
http://repositorio.ufsm.br/handle/1/10540 |
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por |
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100600000000 |
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400 500 300 300 |
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Universidade Federal de Santa Maria |
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UFSM |
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Química |
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Universidade Federal de Santa Maria |
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