Síntese de 2-[3h-pirazol-2-il]trifluormetilpirimidinas Alquil, aril e heteroaril substituidas
Ano de defesa: | 2004 |
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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/1/10391 |
Resumo: | This work describes a general methodology for the synthesis of a novel series of 4-alkyl, 4-aryl, heteroaryl-2-[5-methyl-4-(2-hidroxyethyl)-3-oxo-1,2-dihydro-3H-pyrazol-2-yl]-6(4)-trifluoromethylpyrimidines. The precursors β-alkoxyvinyl trihalomethyl ketones of the general formula, F3C-C(O)-C(R2)=C(R)OR1, where R= H, CH3, i-Pr, Ph, 4-OCH3Ph, 2-C4H3O, 2-C4H3S, R1= CH3, C2H5 and R2 = H, CH3, R-R2= -(CH2)3-, were obtained from trifluoroacetylation reactions of enoleters and acetals derived from alkyl, cicloalkyl, methyl Ketones and 4-substituted acetophenones, propiophenones. And the precursor amidínico synthesized from 2-acetyl-butyrolactone with aminoguanidine bicarbonate in the presence of acetate of ammonium. The compounds objective of this study was obtained from the reaction of cyclocondensation reaction of 4-alkoxy-1,1,1-trifluoro-3-alken-2-ones with 1-amidino-4-(2-hydroxyethyl)-3-methyl-3-pyrazolin-5-one in the presence of anhydrous potassium carbonate. With yield of 35-80%. All the compounds 3H-pyzolil-pyrimidine were identified by 1H, 13C and 19F NMR spectra, IR, CG-MS and the purity of the compounds confirmed for it analyzes elemental. |
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2017-05-152017-05-152004-07-14MARTINS, Demétrius Bernardes. Synthesis of 2-[3h-pyrazol-2-yl]trifluoromethylpyrimidines alkyl, aryl and heteroaril substituted. 2004. 111 f. Dissertação (Mestrado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2004.http://repositorio.ufsm.br/handle/1/10391This work describes a general methodology for the synthesis of a novel series of 4-alkyl, 4-aryl, heteroaryl-2-[5-methyl-4-(2-hidroxyethyl)-3-oxo-1,2-dihydro-3H-pyrazol-2-yl]-6(4)-trifluoromethylpyrimidines. The precursors β-alkoxyvinyl trihalomethyl ketones of the general formula, F3C-C(O)-C(R2)=C(R)OR1, where R= H, CH3, i-Pr, Ph, 4-OCH3Ph, 2-C4H3O, 2-C4H3S, R1= CH3, C2H5 and R2 = H, CH3, R-R2= -(CH2)3-, were obtained from trifluoroacetylation reactions of enoleters and acetals derived from alkyl, cicloalkyl, methyl Ketones and 4-substituted acetophenones, propiophenones. And the precursor amidínico synthesized from 2-acetyl-butyrolactone with aminoguanidine bicarbonate in the presence of acetate of ammonium. The compounds objective of this study was obtained from the reaction of cyclocondensation reaction of 4-alkoxy-1,1,1-trifluoro-3-alken-2-ones with 1-amidino-4-(2-hydroxyethyl)-3-methyl-3-pyrazolin-5-one in the presence of anhydrous potassium carbonate. With yield of 35-80%. All the compounds 3H-pyzolil-pyrimidine were identified by 1H, 13C and 19F NMR spectra, IR, CG-MS and the purity of the compounds confirmed for it analyzes elemental.Este trabalho descreve uma metodologia geral para síntese de uma série de novas 4-alquil-, 4-aril-, 4-heteroaril-2[5-metil-4-(2-hidroxietil)3-oxo-1,2-diidro-3H-pirazol-2-il]-6(4)-trifluormetilpirimidinas. Os precursores β-alcoxivinil trifluorometil cetonas de formula geral F3C-C(O)-C(R2)=C(R)OR1, onde R= H, CH3, i-Pr, Ph, 4-OCH3Ph, 2-C4H3O, 2-C4H3S, R1= CH3, C2H5 e R2 = H, CH3, R-R2= -(CH2)3- foram obtidas a partir de reações de trifluoracetilação de enoléteres e acetais derivados de alquil, cilcloalquil (heteroaril) metil cetonas, acetofenonas e propiofenonas 4-substituidas. E o precursor amidínico sintetizado a partir de 2-acetil-butirolactona reagindo com aminoguanidina bicarbonato na presença de acetato de amônio. Os compostos alvo deste estudo foram obtidos a partir da reação de ciclocondensação de 4-metoxi-4-alquil(aril)(heteroaril)-1,1,1-trifluor-3-alquen-2-onas frente a 5-metil-4-(2-hidroxietil)-3-oxo-1,2-diihidro-3H-2-amidinopirazol na presença de carbonato de potássio anidro, com rendimentos que variaram de 35 80%. Todos os compostos 3H-pizolil-pirimidina foram identificados por técnicas espectroscopicas de RMN (1H, 13C, 19F), IR, e CG-MS e a pureza dos compostos confirmada por analise elementar .Coordenação de Aperfeiçoamento de Pessoal de Nível Superiorapplication/pdfporUniversidade Federal de Santa MariaPrograma de Pós-Graduação em QuímicaUFSMBRQuímicaQuímicaQuímica orgânicaCompostos heterocíclicosPirimidinasSíntese químicaCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese de 2-[3h-pirazol-2-il]trifluormetilpirimidinas Alquil, aril e heteroaril substituidasSynthesis of 2-[3h-pyrazol-2-yl]trifluoromethylpyrimidines alkyl, aryl and heteroaril substitutedinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisBonacorso, Helio Gauzehttp://lattes.cnpq.br/7275608974248322Braibante, Mara Elisa Forteshttp://lattes.cnpq.br/0685197822607977Zanatta, Nilohttp://lattes.cnpq.br/0719465062354576http://lattes.cnpq.br/9853693835496512Martins, Demétrius Bernardes10060000000040050030030050006c852ad-d805-43c3-99d6-93a6a86f507cd2f6e3ea-7dad-4d02-ae8b-fc3e8d5c808d2c128d4d-5411-4956-940a-6ba1d883805d2f7bd6ce-78fa-4968-ac66-2d1407e90f60info:eu-repo/semantics/openAccessreponame:Manancial - Repositório Digital da UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALDEMETRIUS MARTINS.pdfapplication/pdf1433478http://repositorio.ufsm.br/bitstream/1/10391/1/DEMETRIUS%20MARTINS.pdf1a4c41c6a16043b5496f620cc089f7a3MD51TEXTDEMETRIUS MARTINS.pdf.txtDEMETRIUS MARTINS.pdf.txtExtracted texttext/plain105816http://repositorio.ufsm.br/bitstream/1/10391/2/DEMETRIUS%20MARTINS.pdf.txt9a39e0c1f023956718d297f1ea230283MD52THUMBNAILDEMETRIUS MARTINS.pdf.jpgDEMETRIUS MARTINS.pdf.jpgIM Thumbnailimage/jpeg4573http://repositorio.ufsm.br/bitstream/1/10391/3/DEMETRIUS%20MARTINS.pdf.jpg613bd8d0cbed326f1add7652f3e7d389MD531/103912022-06-01 11:40:56.994oai:repositorio.ufsm.br:1/10391Repositório Institucionalhttp://repositorio.ufsm.br/PUBhttp://repositorio.ufsm.br/oai/requestopendoar:39132022-06-01T14:40:56Manancial - Repositório Digital da UFSM - Universidade Federal de Santa Maria (UFSM)false |
dc.title.por.fl_str_mv |
Síntese de 2-[3h-pirazol-2-il]trifluormetilpirimidinas Alquil, aril e heteroaril substituidas |
dc.title.alternative.eng.fl_str_mv |
Synthesis of 2-[3h-pyrazol-2-yl]trifluoromethylpyrimidines alkyl, aryl and heteroaril substituted |
title |
Síntese de 2-[3h-pirazol-2-il]trifluormetilpirimidinas Alquil, aril e heteroaril substituidas |
spellingShingle |
Síntese de 2-[3h-pirazol-2-il]trifluormetilpirimidinas Alquil, aril e heteroaril substituidas Martins, Demétrius Bernardes Química Química orgânica Compostos heterocíclicos Pirimidinas Síntese química CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Síntese de 2-[3h-pirazol-2-il]trifluormetilpirimidinas Alquil, aril e heteroaril substituidas |
title_full |
Síntese de 2-[3h-pirazol-2-il]trifluormetilpirimidinas Alquil, aril e heteroaril substituidas |
title_fullStr |
Síntese de 2-[3h-pirazol-2-il]trifluormetilpirimidinas Alquil, aril e heteroaril substituidas |
title_full_unstemmed |
Síntese de 2-[3h-pirazol-2-il]trifluormetilpirimidinas Alquil, aril e heteroaril substituidas |
title_sort |
Síntese de 2-[3h-pirazol-2-il]trifluormetilpirimidinas Alquil, aril e heteroaril substituidas |
author |
Martins, Demétrius Bernardes |
author_facet |
Martins, Demétrius Bernardes |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Bonacorso, Helio Gauze |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/7275608974248322 |
dc.contributor.referee1.fl_str_mv |
Braibante, Mara Elisa Fortes |
dc.contributor.referee1Lattes.fl_str_mv |
http://lattes.cnpq.br/0685197822607977 |
dc.contributor.referee2.fl_str_mv |
Zanatta, Nilo |
dc.contributor.referee2Lattes.fl_str_mv |
http://lattes.cnpq.br/0719465062354576 |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/9853693835496512 |
dc.contributor.author.fl_str_mv |
Martins, Demétrius Bernardes |
contributor_str_mv |
Bonacorso, Helio Gauze Braibante, Mara Elisa Fortes Zanatta, Nilo |
dc.subject.por.fl_str_mv |
Química Química orgânica Compostos heterocíclicos Pirimidinas Síntese química |
topic |
Química Química orgânica Compostos heterocíclicos Pirimidinas Síntese química CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
This work describes a general methodology for the synthesis of a novel series of 4-alkyl, 4-aryl, heteroaryl-2-[5-methyl-4-(2-hidroxyethyl)-3-oxo-1,2-dihydro-3H-pyrazol-2-yl]-6(4)-trifluoromethylpyrimidines. The precursors β-alkoxyvinyl trihalomethyl ketones of the general formula, F3C-C(O)-C(R2)=C(R)OR1, where R= H, CH3, i-Pr, Ph, 4-OCH3Ph, 2-C4H3O, 2-C4H3S, R1= CH3, C2H5 and R2 = H, CH3, R-R2= -(CH2)3-, were obtained from trifluoroacetylation reactions of enoleters and acetals derived from alkyl, cicloalkyl, methyl Ketones and 4-substituted acetophenones, propiophenones. And the precursor amidínico synthesized from 2-acetyl-butyrolactone with aminoguanidine bicarbonate in the presence of acetate of ammonium. The compounds objective of this study was obtained from the reaction of cyclocondensation reaction of 4-alkoxy-1,1,1-trifluoro-3-alken-2-ones with 1-amidino-4-(2-hydroxyethyl)-3-methyl-3-pyrazolin-5-one in the presence of anhydrous potassium carbonate. With yield of 35-80%. All the compounds 3H-pyzolil-pyrimidine were identified by 1H, 13C and 19F NMR spectra, IR, CG-MS and the purity of the compounds confirmed for it analyzes elemental. |
publishDate |
2004 |
dc.date.issued.fl_str_mv |
2004-07-14 |
dc.date.accessioned.fl_str_mv |
2017-05-15 |
dc.date.available.fl_str_mv |
2017-05-15 |
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 |
MARTINS, Demétrius Bernardes. Synthesis of 2-[3h-pyrazol-2-yl]trifluoromethylpyrimidines alkyl, aryl and heteroaril substituted. 2004. 111 f. Dissertação (Mestrado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2004. |
dc.identifier.uri.fl_str_mv |
http://repositorio.ufsm.br/handle/1/10391 |
identifier_str_mv |
MARTINS, Demétrius Bernardes. Synthesis of 2-[3h-pyrazol-2-yl]trifluoromethylpyrimidines alkyl, aryl and heteroaril substituted. 2004. 111 f. Dissertação (Mestrado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2004. |
url |
http://repositorio.ufsm.br/handle/1/10391 |
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Universidade Federal de Santa Maria |
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