Síntese de 2-[3h-pirazol-2-il]trifluormetilpirimidinas Alquil, aril e heteroaril substituidas
Autor(a) principal: | |
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Data de Publicação: | 2004 |
Tipo de documento: | Dissertação |
Idioma: | por |
Título da fonte: | Manancial - Repositório Digital da UFSM |
Texto Completo: | 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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Síntese de 2-[3h-pirazol-2-il]trifluormetilpirimidinas Alquil, aril e heteroaril substituidasSynthesis of 2-[3h-pyrazol-2-yl]trifluoromethylpyrimidines alkyl, aryl and heteroaril substitutedQuímicaQuímica orgânicaCompostos heterocíclicosPirimidinasSíntese químicaCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICAThis 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.Coordenação de Aperfeiçoamento de Pessoal de Nível SuperiorEste 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 .Universidade Federal de Santa MariaBRQuímicaUFSMPrograma de Pós-Graduação em QuímicaBonacorso, Helio Gauzehttp://lattes.cnpq.br/7275608974248322Braibante, Mara Elisa Forteshttp://lattes.cnpq.br/0685197822607977Zanatta, Nilohttp://lattes.cnpq.br/0719465062354576Martins, Demétrius Bernardes2017-05-152017-05-152004-07-14info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisapplication/pdfapplication/pdfMARTINS, 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/1/10391porinfo:eu-repo/semantics/openAccessreponame:Manancial - Repositório Digital da UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSM2022-06-01T14:40:56Zoai:repositorio.ufsm.br:1/10391Biblioteca Digital de Teses e Dissertaçõeshttps://repositorio.ufsm.br/ONGhttps://repositorio.ufsm.br/oai/requestatendimento.sib@ufsm.br||tedebc@gmail.comopendoar:2022-06-01T14:40:56Manancial - Repositório Digital da UFSM - Universidade Federal de Santa Maria (UFSM)false |
dc.title.none.fl_str_mv |
Síntese de 2-[3h-pirazol-2-il]trifluormetilpirimidinas Alquil, aril e heteroaril substituidas 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.none.fl_str_mv |
Bonacorso, Helio Gauze http://lattes.cnpq.br/7275608974248322 Braibante, Mara Elisa Fortes http://lattes.cnpq.br/0685197822607977 Zanatta, Nilo http://lattes.cnpq.br/0719465062354576 |
dc.contributor.author.fl_str_mv |
Martins, Demétrius Bernardes |
dc.subject.por.fl_str_mv |
Química Química orgânica Compostos heterocíclicos Pirimidinas Síntese química CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
topic |
Química Química orgânica Compostos heterocíclicos Pirimidinas Síntese química 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.none.fl_str_mv |
2004-07-14 2017-05-15 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.uri.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. 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 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
application/pdf application/pdf |
dc.publisher.none.fl_str_mv |
Universidade Federal de Santa Maria BR Química UFSM Programa de Pós-Graduação em Química |
publisher.none.fl_str_mv |
Universidade Federal de Santa Maria BR Química UFSM Programa de Pós-Graduação em Química |
dc.source.none.fl_str_mv |
reponame:Manancial - Repositório Digital da UFSM instname:Universidade Federal de Santa Maria (UFSM) instacron:UFSM |
instname_str |
Universidade Federal de Santa Maria (UFSM) |
instacron_str |
UFSM |
institution |
UFSM |
reponame_str |
Manancial - Repositório Digital da UFSM |
collection |
Manancial - Repositório Digital da UFSM |
repository.name.fl_str_mv |
Manancial - Repositório Digital da UFSM - Universidade Federal de Santa Maria (UFSM) |
repository.mail.fl_str_mv |
atendimento.sib@ufsm.br||tedebc@gmail.com |
_version_ |
1805922095554625536 |