Síntese de triazolopirimidinas 7-triclorometil e triazolopirimidinonas substituídas a partir de reações entre 4-alcóxi-1,1,1-tricloro-3-alquen-2-onas e 3-amino-1H-1,2,4-triazóis
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
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/1/22458 |
Resumo: | A synthetic strategy was developed for obtaining a series of new 7- trichloromethyl-[1,2,4]-triazolo-[1,5-a]pyrimidines substituted from cyclocondensation reaction between 4-alkoxy-1,1,1-trichloro-3-alken-2-ones (enones 1) of the general formula: RO-C(R2)=C(R1)C(O)CCl3 (where R = Me, Et, R1 = H, Me, R-R1 = -(CH2)2, - (CH 2)3- and R2= H, Me, C6H5, 4-F-C6H4, 4-OMe-C6H4) and 3-amino-1H-[1,2,4]triazol- 5-substituted (H (2), CO2H (3), SMe (4)) via a single step reaction using a simple and efficient method. In a second step, in order to exploit the synthetic versatility of the trichloromethyl group, were performed cyclocondensation reactions in basic medium using the enones 1 and 3-amino-1H-[1,2,4]triazole (2-4) to obtain a series of 1,2,4- triazolo-[1,5-a]pyrimidinones. The 7-trichloromethyl-[1,2,4]triazolo-[1,5-a]pyrimidines and 1,2,4-triazolo-[1,5- a]pyrimidinones were obtained from 50% to 85 % yield, and purified by recrystallization from ethanol. The reaction of enones 1 with 3-amino-1H-[1,2,4]- triazole-5-carboxylic acid 4 led to the formation of the respective triazolopyrimidines, however, under all reaction conditions tested, decarboxylation of the triazole was observed. The most cyclocondensation reaction of enones 1 with 3-amino-1H-[1,2,4] triazole (2,3) led only to obtain the 2,7-isomer of the 1,2,4-triazolo-[1,5-a]pyrimidines. With some enones it was observed the formation of a small amount the 2,5 isomer. As for the triazole pyrimidinones were formed on both isomers depending enone used. The products obtained in this work were characterized by Nuclear Magnetic Resonance of Hydrogen and Carbon-13, Mass Spectrometry and its degree of purity proven via Elemental analysis was also possible to establish some structures by Xray diffraction. |
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oai:repositorio.ufsm.br:1/22458 |
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Manancial - Repositório Digital da UFSM |
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spelling |
2021-10-19T14:01:54Z2021-10-19T14:01:54Z2013-08-02http://repositorio.ufsm.br/handle/1/22458A synthetic strategy was developed for obtaining a series of new 7- trichloromethyl-[1,2,4]-triazolo-[1,5-a]pyrimidines substituted from cyclocondensation reaction between 4-alkoxy-1,1,1-trichloro-3-alken-2-ones (enones 1) of the general formula: RO-C(R2)=C(R1)C(O)CCl3 (where R = Me, Et, R1 = H, Me, R-R1 = -(CH2)2, - (CH 2)3- and R2= H, Me, C6H5, 4-F-C6H4, 4-OMe-C6H4) and 3-amino-1H-[1,2,4]triazol- 5-substituted (H (2), CO2H (3), SMe (4)) via a single step reaction using a simple and efficient method. In a second step, in order to exploit the synthetic versatility of the trichloromethyl group, were performed cyclocondensation reactions in basic medium using the enones 1 and 3-amino-1H-[1,2,4]triazole (2-4) to obtain a series of 1,2,4- triazolo-[1,5-a]pyrimidinones. The 7-trichloromethyl-[1,2,4]triazolo-[1,5-a]pyrimidines and 1,2,4-triazolo-[1,5- a]pyrimidinones were obtained from 50% to 85 % yield, and purified by recrystallization from ethanol. The reaction of enones 1 with 3-amino-1H-[1,2,4]- triazole-5-carboxylic acid 4 led to the formation of the respective triazolopyrimidines, however, under all reaction conditions tested, decarboxylation of the triazole was observed. The most cyclocondensation reaction of enones 1 with 3-amino-1H-[1,2,4] triazole (2,3) led only to obtain the 2,7-isomer of the 1,2,4-triazolo-[1,5-a]pyrimidines. With some enones it was observed the formation of a small amount the 2,5 isomer. As for the triazole pyrimidinones were formed on both isomers depending enone used. The products obtained in this work were characterized by Nuclear Magnetic Resonance of Hydrogen and Carbon-13, Mass Spectrometry and its degree of purity proven via Elemental analysis was also possible to establish some structures by Xray diffraction.Uma estratégia sintética foi desenvolvida para a obtenção de novas 7- triclorometil-[1,2,4]triazolo-[1,5-a]pirimidinas substituídas a partir da ciclocondensação entre 4-alcóxi-1,1,1-tricloro-3-alquen-2-onas (enonas 1) de fórmula geral: RO-C(R2)=C(R1)C(O)CCl3 (onde R = Me, Et; R1 = H, Me; R-R1= - (CH2)2, -(CH2)3 e R2 = H, Me, C6H5, 4-F-C6H4, 4-OMe-C6H4) e 3-amino-1H-(1,2,4)- triazol 5-substituídos (2-4) (H, SMe CO2H), através de um único passo reacional, utilizando uma metodologia simples e eficiente. Em uma segunda etapa, visando explorar a versatilidade sintética do grupo tricolorometila, foram realizadas reações de ciclocondensação em meio básico utilizando as enonas 1 e 3-amino-1H-[1,2,4]triazóis (2-4) para obter uma série de 1,2,4-triazolo-[1,5-a]pirimidinonas. As 7-triclorometil-[1,2,4]triazolo-[1,5-a]pirimidinas e as respectivas 1,2,4- triazolo[1,5-a]pirimidinonas foram obtidas com rendimentos entre 50% a 85%, sendo purificadas através de recristalização em etanol. A reação das enonas 1 com o ácido 3-amino-1H-[1,2,4]-triazol-5-carboxílico 4 levou à formação das respectivas triazolopirimidinas, porém, sob todas as condições reacionais testadas, houve a descarboxilação do triazol durante a síntese. A maior parte das reações de ciclocondensação das enonas 1 com os 3-amino- 1H-[1,2,4]triazóis (2,3), conduzidas em meio ácido, levaram somente à obtenção do isômero-2,7 das 1,2,4-triazolo-[1,5-a]pirimidinas. Com algumas enonas observou-se a formação de uma pequena quantidade do isômero-2,5. Já para a mesma reação de ciclocondensação, realizada em meio básico, as houve a formação de ambos os isômeros das triazolo pirimidinonas dependendo da estrutura da enona utilizada. Os produtos obtidos neste trabalho foram caracterizados por Ressonância Magnética Nuclear de Hidrogênio e Carbono-13, Espectrometria de Massas e seus graus de pureza comprovados via Análise Elementar e também foi possível comprovar algumas estruturas por difração de Raios-X.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/openAccess1,2,4-triazolo-[1,5-a]pirimidinas3-amino-[1,2,4]triazol4-alcóxi- 1,1,1-tricloro-3-alquen-2-onasEnonasEnones1,2,4-triazolo-[1,5-a]pirimidine3-amino-[1,2,4]triazole4-alkoxy-1,1,1- trichloro-3-alken-2-onesCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese de triazolopirimidinas 7-triclorometil e triazolopirimidinonas substituídas a partir de reações entre 4-alcóxi-1,1,1-tricloro-3-alquen-2-onas e 3-amino-1H-1,2,4-triazóisSynthesis of 7-trichloromethyl triazolopyrimidines and triazolopirimidinines substituted from reaction between 4-alkoxy-1,1,1-trichloro-3-alken-2-ones and 3-amino-1H-1,2,4-triazoleinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisZanatta, Nilohttp://lattes.cnpq.br/0719465062354576Rodrigues, Oscar Endrigo DornelesFantinel, Leonardohttp://lattes.cnpq.br/6780911889587685Souza, Laura de Andrade100600000000600600600233dc1de-ab03-4f57-9b85-e40dc01a2d4f74a79d75-2e9f-4907-b012-dfb4582a9745d315e5ef-8c77-48c9-bc87-e90cab9c43e9079f4612-cd36-4354-af6f-25f7736dccd2reponame:Manancial - Repositório Digital da UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMLICENSElicense.txtlicense.txttext/plain; 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dc.title.por.fl_str_mv |
Síntese de triazolopirimidinas 7-triclorometil e triazolopirimidinonas substituídas a partir de reações entre 4-alcóxi-1,1,1-tricloro-3-alquen-2-onas e 3-amino-1H-1,2,4-triazóis |
dc.title.alternative.eng.fl_str_mv |
Synthesis of 7-trichloromethyl triazolopyrimidines and triazolopirimidinines substituted from reaction between 4-alkoxy-1,1,1-trichloro-3-alken-2-ones and 3-amino-1H-1,2,4-triazole |
title |
Síntese de triazolopirimidinas 7-triclorometil e triazolopirimidinonas substituídas a partir de reações entre 4-alcóxi-1,1,1-tricloro-3-alquen-2-onas e 3-amino-1H-1,2,4-triazóis |
spellingShingle |
Síntese de triazolopirimidinas 7-triclorometil e triazolopirimidinonas substituídas a partir de reações entre 4-alcóxi-1,1,1-tricloro-3-alquen-2-onas e 3-amino-1H-1,2,4-triazóis Souza, Laura de Andrade 1,2,4-triazolo-[1,5-a]pirimidinas 3-amino-[1,2,4]triazol 4-alcóxi- 1,1,1-tricloro-3-alquen-2-onas Enonas Enones 1,2,4-triazolo-[1,5-a]pirimidine 3-amino-[1,2,4]triazole 4-alkoxy-1,1,1- trichloro-3-alken-2-ones CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Síntese de triazolopirimidinas 7-triclorometil e triazolopirimidinonas substituídas a partir de reações entre 4-alcóxi-1,1,1-tricloro-3-alquen-2-onas e 3-amino-1H-1,2,4-triazóis |
title_full |
Síntese de triazolopirimidinas 7-triclorometil e triazolopirimidinonas substituídas a partir de reações entre 4-alcóxi-1,1,1-tricloro-3-alquen-2-onas e 3-amino-1H-1,2,4-triazóis |
title_fullStr |
Síntese de triazolopirimidinas 7-triclorometil e triazolopirimidinonas substituídas a partir de reações entre 4-alcóxi-1,1,1-tricloro-3-alquen-2-onas e 3-amino-1H-1,2,4-triazóis |
title_full_unstemmed |
Síntese de triazolopirimidinas 7-triclorometil e triazolopirimidinonas substituídas a partir de reações entre 4-alcóxi-1,1,1-tricloro-3-alquen-2-onas e 3-amino-1H-1,2,4-triazóis |
title_sort |
Síntese de triazolopirimidinas 7-triclorometil e triazolopirimidinonas substituídas a partir de reações entre 4-alcóxi-1,1,1-tricloro-3-alquen-2-onas e 3-amino-1H-1,2,4-triazóis |
author |
Souza, Laura de Andrade |
author_facet |
Souza, Laura de Andrade |
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 |
Rodrigues, Oscar Endrigo Dorneles |
dc.contributor.referee2.fl_str_mv |
Fantinel, Leonardo |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/6780911889587685 |
dc.contributor.author.fl_str_mv |
Souza, Laura de Andrade |
contributor_str_mv |
Zanatta, Nilo Rodrigues, Oscar Endrigo Dorneles Fantinel, Leonardo |
dc.subject.por.fl_str_mv |
1,2,4-triazolo-[1,5-a]pirimidinas 3-amino-[1,2,4]triazol 4-alcóxi- 1,1,1-tricloro-3-alquen-2-onas Enonas Enones |
topic |
1,2,4-triazolo-[1,5-a]pirimidinas 3-amino-[1,2,4]triazol 4-alcóxi- 1,1,1-tricloro-3-alquen-2-onas Enonas Enones 1,2,4-triazolo-[1,5-a]pirimidine 3-amino-[1,2,4]triazole 4-alkoxy-1,1,1- trichloro-3-alken-2-ones CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.eng.fl_str_mv |
1,2,4-triazolo-[1,5-a]pirimidine 3-amino-[1,2,4]triazole 4-alkoxy-1,1,1- trichloro-3-alken-2-ones |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
A synthetic strategy was developed for obtaining a series of new 7- trichloromethyl-[1,2,4]-triazolo-[1,5-a]pyrimidines substituted from cyclocondensation reaction between 4-alkoxy-1,1,1-trichloro-3-alken-2-ones (enones 1) of the general formula: RO-C(R2)=C(R1)C(O)CCl3 (where R = Me, Et, R1 = H, Me, R-R1 = -(CH2)2, - (CH 2)3- and R2= H, Me, C6H5, 4-F-C6H4, 4-OMe-C6H4) and 3-amino-1H-[1,2,4]triazol- 5-substituted (H (2), CO2H (3), SMe (4)) via a single step reaction using a simple and efficient method. In a second step, in order to exploit the synthetic versatility of the trichloromethyl group, were performed cyclocondensation reactions in basic medium using the enones 1 and 3-amino-1H-[1,2,4]triazole (2-4) to obtain a series of 1,2,4- triazolo-[1,5-a]pyrimidinones. The 7-trichloromethyl-[1,2,4]triazolo-[1,5-a]pyrimidines and 1,2,4-triazolo-[1,5- a]pyrimidinones were obtained from 50% to 85 % yield, and purified by recrystallization from ethanol. The reaction of enones 1 with 3-amino-1H-[1,2,4]- triazole-5-carboxylic acid 4 led to the formation of the respective triazolopyrimidines, however, under all reaction conditions tested, decarboxylation of the triazole was observed. The most cyclocondensation reaction of enones 1 with 3-amino-1H-[1,2,4] triazole (2,3) led only to obtain the 2,7-isomer of the 1,2,4-triazolo-[1,5-a]pyrimidines. With some enones it was observed the formation of a small amount the 2,5 isomer. As for the triazole pyrimidinones were formed on both isomers depending enone used. The products obtained in this work were characterized by Nuclear Magnetic Resonance of Hydrogen and Carbon-13, Mass Spectrometry and its degree of purity proven via Elemental analysis was also possible to establish some structures by Xray diffraction. |
publishDate |
2013 |
dc.date.issued.fl_str_mv |
2013-08-02 |
dc.date.accessioned.fl_str_mv |
2021-10-19T14:01:54Z |
dc.date.available.fl_str_mv |
2021-10-19T14:01:54Z |
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/1/22458 |
url |
http://repositorio.ufsm.br/handle/1/22458 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.relation.cnpq.fl_str_mv |
100600000000 |
dc.relation.confidence.fl_str_mv |
600 600 600 |
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/ |
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openAccess |
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Universidade Federal de Santa Maria Centro de Ciências Naturais e Exatas |
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Programa de Pós-Graduação em Química |
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UFSM |
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Brasil |
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Química |
publisher.none.fl_str_mv |
Universidade Federal de Santa Maria Centro de Ciências Naturais e Exatas |
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Universidade Federal de Santa Maria (UFSM) |
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UFSM |
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UFSM |
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Manancial - Repositório Digital da UFSM |
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Manancial - Repositório Digital da UFSM |
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