Síntese de 2-(1h-pirazol-1-il)-5-(1h-pirazol-1-il-1-carbonil) piridinas
Autor(a) principal: | |
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Data de Publicação: | 2008 |
Tipo de documento: | Dissertação |
Idioma: | por |
Título da fonte: | Manancial - Repositório Digital da UFSM |
Texto Completo: | http://repositorio.ufsm.br/handle/1/10419 |
Resumo: | This work describes the synthesis of a new series of 2-[3-alkyl(aryl/heteroaryl)-5-trihalomethyl-5-hydroxy-4,5-dihydro-1H-pyrazol-1-il]-5-[3-alkyl(aryl/heteroaryl)-5-trihalomethyl-5-hydroxy-4,5-dihydro-1H-pyrazol-1-il-1-carbonyl]pyridines by the cyclocondensation reaction of 1,1,1-trihalo-4-alkoxy-4-alkyl(aryl/heteroaryl)-3-alken-2- ones [CX3C(O)CH=CR1OR, where R = Me, Et; R1 = H, Me, Ph, 4-MeOPh, 4-NO2Ph, 4,4 -Biphenyl, 1-Naftyl, 2-Furyl, 2-Thienyl and X = F, Cl] with 6-hydraninonicotinic hydrazide hydrate. Yields of 67 to 97% was obtained when the reactions were performed in ethanol as a solvent to 78 oC for 4 hours. In a subsequent step are described the reactions of dehydration intramolecular of 2- (1H-pyrazol-1-yl)-5-(1H pyrazol-1-yl-1-carbonyl)pyridines. These reactions were carried out in pyridine/benzene in the presence of thionyl chloride and led to the isolation of a series of 2- [3-alkyl (aryl/heteroaryl)-5-trihalomethyl-1H- pyrazol-1-yl]-5-3-alkyl (aryl/heteroaryl)-5-trihalomethyl-1H-pyrazol-1-yl-1-carbonyl]pyridine, with yields of 64 to 86%. All compounds were characterized by analytical experiments 1Hs and 13Cs, 2DCOLOQ NMR, mass spectrometry (GC-MSD) and its purities they were determined by CHN elemental analysis. |
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Síntese de 2-(1h-pirazol-1-il)-5-(1h-pirazol-1-il-1-carbonil) piridinasSynthesis of 2-(1h-pyrazol-1-il)-5-(1h-pyrazol-1-il-1-carbonyl) pyridinesQuímicaQuímica orgânicaCompostos químicosCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICAThis work describes the synthesis of a new series of 2-[3-alkyl(aryl/heteroaryl)-5-trihalomethyl-5-hydroxy-4,5-dihydro-1H-pyrazol-1-il]-5-[3-alkyl(aryl/heteroaryl)-5-trihalomethyl-5-hydroxy-4,5-dihydro-1H-pyrazol-1-il-1-carbonyl]pyridines by the cyclocondensation reaction of 1,1,1-trihalo-4-alkoxy-4-alkyl(aryl/heteroaryl)-3-alken-2- ones [CX3C(O)CH=CR1OR, where R = Me, Et; R1 = H, Me, Ph, 4-MeOPh, 4-NO2Ph, 4,4 -Biphenyl, 1-Naftyl, 2-Furyl, 2-Thienyl and X = F, Cl] with 6-hydraninonicotinic hydrazide hydrate. Yields of 67 to 97% was obtained when the reactions were performed in ethanol as a solvent to 78 oC for 4 hours. In a subsequent step are described the reactions of dehydration intramolecular of 2- (1H-pyrazol-1-yl)-5-(1H pyrazol-1-yl-1-carbonyl)pyridines. These reactions were carried out in pyridine/benzene in the presence of thionyl chloride and led to the isolation of a series of 2- [3-alkyl (aryl/heteroaryl)-5-trihalomethyl-1H- pyrazol-1-yl]-5-3-alkyl (aryl/heteroaryl)-5-trihalomethyl-1H-pyrazol-1-yl-1-carbonyl]pyridine, with yields of 64 to 86%. All compounds were characterized by analytical experiments 1Hs and 13Cs, 2DCOLOQ NMR, mass spectrometry (GC-MSD) and its purities they were determined by CHN elemental analysis.Coordenação de Aperfeiçoamento de Pessoal de Nível SuperiorEsta dissertação apresenta a síntese de uma nova série de 2-[3-alquil (aril/heteroaril)-5-trialometil-5-hidroxi-4,5-diidro-1H-pirazol-1-il]-5-[3- alquil(aril/heteroaril)-5-trialometil-5-hidroxi-4,5-diidro-1H-pirazol-1-il-1- carbonil]piridinas, obtida a partir de reações de ciclocondensação de 1,1,1-trialo-4- alquil(aril/heteroaril)-4-alcoxi-3-alquen-2-onas [CX3C(O)CH=CR1OR, onde R = Me, Et; R1 = H, Me, Ph, 4-MeOPh, 4-NO2Ph, 4,4 -Bifenil, 1-Naftil, Fur-2-il e Tien-2-il e X = F, Cl] com hidrazida 6-hidrazino nicotínica. Rendimentos de 67 a 97% foram obtidos quando as reações foram executadas em etanol como solvente a 78 oC por 4 horas. Numa etapa posterior, são descritas as reações de desidratação intramolecular de 2- (1H-pirazol-1-il)-5-(1H-pirazol-1-il-1-carbonil) piridinas. Estas reações foram realizadas em meio piridina/benzeno, na presença de cloreto de tionila e levaram ao isolamento de uma série de 2-[3-alquil(aril/heteroaril)-5-trifluormetil-1H-pirazol-1-il]-5-[3-alquil (aril/ heteroaril)-5-trifluormetil-1H-pirazol-1-il-1-carbonil]piridina, com rendimentos de 64 a 86%. Os compostos foram caracterizados por experimentos de RMN de 1H, RMN de 13C {1H} e RMN 2D COLOQ, espectroscopia de massas (GC-MSD) e as suas purezas foram determinadas por análise elementar CHN.Universidade Federal de Santa MariaBRQuímicaUFSMPrograma de Pós-Graduação em QuímicaBonacorso, Helio Gauzehttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4788537E0Martins, Marcos Antonio Pintohttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4783192P3Flores, Alex Fabiani Clarohttp://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4782774Y0Paim, Gisele Rocha2017-05-162017-05-162008-02-20info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisapplication/pdfapplication/pdfPAIM, Gisele Rocha. Synthesis of 2-(1h-pyrazol-1-il)-5-(1h-pyrazol-1-il-1-carbonyl) pyridines. 2008. 134 f. Dissertação (Mestrado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2008.http://repositorio.ufsm.br/handle/1/10419porinfo:eu-repo/semantics/openAccessreponame:Manancial - Repositório Digital da UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSM2017-07-25T15:03:13Zoai:repositorio.ufsm.br:1/10419Biblioteca Digital de Teses e Dissertaçõeshttps://repositorio.ufsm.br/ONGhttps://repositorio.ufsm.br/oai/requestatendimento.sib@ufsm.br||tedebc@gmail.comopendoar:2017-07-25T15:03:13Manancial - Repositório Digital da UFSM - Universidade Federal de Santa Maria (UFSM)false |
dc.title.none.fl_str_mv |
Síntese de 2-(1h-pirazol-1-il)-5-(1h-pirazol-1-il-1-carbonil) piridinas Synthesis of 2-(1h-pyrazol-1-il)-5-(1h-pyrazol-1-il-1-carbonyl) pyridines |
title |
Síntese de 2-(1h-pirazol-1-il)-5-(1h-pirazol-1-il-1-carbonil) piridinas |
spellingShingle |
Síntese de 2-(1h-pirazol-1-il)-5-(1h-pirazol-1-il-1-carbonil) piridinas Paim, Gisele Rocha Química Química orgânica Compostos químicos CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Síntese de 2-(1h-pirazol-1-il)-5-(1h-pirazol-1-il-1-carbonil) piridinas |
title_full |
Síntese de 2-(1h-pirazol-1-il)-5-(1h-pirazol-1-il-1-carbonil) piridinas |
title_fullStr |
Síntese de 2-(1h-pirazol-1-il)-5-(1h-pirazol-1-il-1-carbonil) piridinas |
title_full_unstemmed |
Síntese de 2-(1h-pirazol-1-il)-5-(1h-pirazol-1-il-1-carbonil) piridinas |
title_sort |
Síntese de 2-(1h-pirazol-1-il)-5-(1h-pirazol-1-il-1-carbonil) piridinas |
author |
Paim, Gisele Rocha |
author_facet |
Paim, Gisele Rocha |
author_role |
author |
dc.contributor.none.fl_str_mv |
Bonacorso, Helio Gauze http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4788537E0 Martins, Marcos Antonio Pinto http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4783192P3 Flores, Alex Fabiani Claro http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4782774Y0 |
dc.contributor.author.fl_str_mv |
Paim, Gisele Rocha |
dc.subject.por.fl_str_mv |
Química Química orgânica Compostos químicos CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
topic |
Química Química orgânica Compostos químicos CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
This work describes the synthesis of a new series of 2-[3-alkyl(aryl/heteroaryl)-5-trihalomethyl-5-hydroxy-4,5-dihydro-1H-pyrazol-1-il]-5-[3-alkyl(aryl/heteroaryl)-5-trihalomethyl-5-hydroxy-4,5-dihydro-1H-pyrazol-1-il-1-carbonyl]pyridines by the cyclocondensation reaction of 1,1,1-trihalo-4-alkoxy-4-alkyl(aryl/heteroaryl)-3-alken-2- ones [CX3C(O)CH=CR1OR, where R = Me, Et; R1 = H, Me, Ph, 4-MeOPh, 4-NO2Ph, 4,4 -Biphenyl, 1-Naftyl, 2-Furyl, 2-Thienyl and X = F, Cl] with 6-hydraninonicotinic hydrazide hydrate. Yields of 67 to 97% was obtained when the reactions were performed in ethanol as a solvent to 78 oC for 4 hours. In a subsequent step are described the reactions of dehydration intramolecular of 2- (1H-pyrazol-1-yl)-5-(1H pyrazol-1-yl-1-carbonyl)pyridines. These reactions were carried out in pyridine/benzene in the presence of thionyl chloride and led to the isolation of a series of 2- [3-alkyl (aryl/heteroaryl)-5-trihalomethyl-1H- pyrazol-1-yl]-5-3-alkyl (aryl/heteroaryl)-5-trihalomethyl-1H-pyrazol-1-yl-1-carbonyl]pyridine, with yields of 64 to 86%. All compounds were characterized by analytical experiments 1Hs and 13Cs, 2DCOLOQ NMR, mass spectrometry (GC-MSD) and its purities they were determined by CHN elemental analysis. |
publishDate |
2008 |
dc.date.none.fl_str_mv |
2008-02-20 2017-05-16 2017-05-16 |
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 |
PAIM, Gisele Rocha. Synthesis of 2-(1h-pyrazol-1-il)-5-(1h-pyrazol-1-il-1-carbonyl) pyridines. 2008. 134 f. Dissertação (Mestrado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2008. http://repositorio.ufsm.br/handle/1/10419 |
identifier_str_mv |
PAIM, Gisele Rocha. Synthesis of 2-(1h-pyrazol-1-il)-5-(1h-pyrazol-1-il-1-carbonyl) pyridines. 2008. 134 f. Dissertação (Mestrado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2008. |
url |
http://repositorio.ufsm.br/handle/1/10419 |
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_ |
1805922048009043968 |