Síntese de 2-(1h-pirazol-1-il)-5-(1h-pirazol-1-il-1-carbonil) piridinas
Autor(a) principal: | |
---|---|
Data de Publicação: | 2008 |
Tipo de documento: | Dissertação |
Idioma: | por |
Título da fonte: | Repositório Institucional Manancial 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. |
id |
UFSM-20_6bd74d552426aa14927efe5f65f54270 |
---|---|
oai_identifier_str |
oai:repositorio.ufsm.br:1/10419 |
network_acronym_str |
UFSM-20 |
network_name_str |
Repositório Institucional Manancial UFSM |
repository_id_str |
3913 |
spelling |
2017-05-162017-05-162008-02-20PAIM, 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/1/10419This 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.Esta 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.Coordenação de Aperfeiçoamento de Pessoal de Nível Superiorapplication/pdfporUniversidade Federal de Santa MariaPrograma de Pós-Graduação em QuímicaUFSMBRQuímicaQuímicaQuímica orgânicaCompostos químicosCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICASíntese 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) pyridinesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisBonacorso, 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=K4782774Y0http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4750098Z3Paim, Gisele Rocha10060000000040050050050050006c852ad-d805-43c3-99d6-93a6a86f507c5ba24abc-fbee-40c9-ad46-4fd9503cde91a8bc3c8e-4034-458b-a211-6be4a0d7001b17a00027-8984-4561-9228-46697f540c2binfo:eu-repo/semantics/openAccessreponame:Repositório Institucional Manancial UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALGISELEPAIM.pdfapplication/pdf2549446http://repositorio.ufsm.br/bitstream/1/10419/1/GISELEPAIM.pdfd624efa0aab323604650c4e5d43e979fMD51TEXTGISELEPAIM.pdf.txtGISELEPAIM.pdf.txtExtracted texttext/plain175715http://repositorio.ufsm.br/bitstream/1/10419/2/GISELEPAIM.pdf.txt3db66443545f9cdc07f92b8922d2ccf9MD52THUMBNAILGISELEPAIM.pdf.jpgGISELEPAIM.pdf.jpgIM Thumbnailimage/jpeg5717http://repositorio.ufsm.br/bitstream/1/10419/3/GISELEPAIM.pdf.jpga870ca50934fedec3bad1dc0a9c29a6aMD531/104192017-07-25 12:03:13.313oai:repositorio.ufsm.br:1/10419Repositório Institucionalhttp://repositorio.ufsm.br/PUBhttp://repositorio.ufsm.br/oai/requestouvidoria@ufsm.bropendoar:39132017-07-25T15:03:13Repositório Institucional Manancial UFSM - Universidade Federal de Santa Maria (UFSM)false |
dc.title.por.fl_str_mv |
Síntese de 2-(1h-pirazol-1-il)-5-(1h-pirazol-1-il-1-carbonil) piridinas |
dc.title.alternative.eng.fl_str_mv |
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.advisor1.fl_str_mv |
Bonacorso, Helio Gauze |
dc.contributor.advisor1Lattes.fl_str_mv |
http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4788537E0 |
dc.contributor.referee1.fl_str_mv |
Martins, Marcos Antonio Pinto |
dc.contributor.referee1Lattes.fl_str_mv |
http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4783192P3 |
dc.contributor.referee2.fl_str_mv |
Flores, Alex Fabiani Claro |
dc.contributor.referee2Lattes.fl_str_mv |
http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4782774Y0 |
dc.contributor.authorLattes.fl_str_mv |
http://buscatextual.cnpq.br/buscatextual/visualizacv.do?id=K4750098Z3 |
dc.contributor.author.fl_str_mv |
Paim, Gisele Rocha |
contributor_str_mv |
Bonacorso, Helio Gauze Martins, Marcos Antonio Pinto Flores, Alex Fabiani Claro |
dc.subject.por.fl_str_mv |
Química Química orgânica Compostos químicos |
topic |
Química Química orgânica Compostos químicos CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.cnpq.fl_str_mv |
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.issued.fl_str_mv |
2008-02-20 |
dc.date.accessioned.fl_str_mv |
2017-05-16 |
dc.date.available.fl_str_mv |
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.citation.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. |
dc.identifier.uri.fl_str_mv |
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.relation.cnpq.fl_str_mv |
100600000000 |
dc.relation.confidence.fl_str_mv |
400 500 500 500 500 |
dc.relation.authority.fl_str_mv |
06c852ad-d805-43c3-99d6-93a6a86f507c 5ba24abc-fbee-40c9-ad46-4fd9503cde91 a8bc3c8e-4034-458b-a211-6be4a0d7001b 17a00027-8984-4561-9228-46697f540c2b |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
application/pdf |
dc.publisher.none.fl_str_mv |
Universidade Federal de Santa Maria |
dc.publisher.program.fl_str_mv |
Programa de Pós-Graduação em Química |
dc.publisher.initials.fl_str_mv |
UFSM |
dc.publisher.country.fl_str_mv |
BR |
dc.publisher.department.fl_str_mv |
Química |
publisher.none.fl_str_mv |
Universidade Federal de Santa Maria |
dc.source.none.fl_str_mv |
reponame:Repositório Institucional Manancial 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 |
Repositório Institucional Manancial UFSM |
collection |
Repositório Institucional Manancial UFSM |
bitstream.url.fl_str_mv |
http://repositorio.ufsm.br/bitstream/1/10419/1/GISELEPAIM.pdf http://repositorio.ufsm.br/bitstream/1/10419/2/GISELEPAIM.pdf.txt http://repositorio.ufsm.br/bitstream/1/10419/3/GISELEPAIM.pdf.jpg |
bitstream.checksum.fl_str_mv |
d624efa0aab323604650c4e5d43e979f 3db66443545f9cdc07f92b8922d2ccf9 a870ca50934fedec3bad1dc0a9c29a6a |
bitstream.checksumAlgorithm.fl_str_mv |
MD5 MD5 MD5 |
repository.name.fl_str_mv |
Repositório Institucional Manancial UFSM - Universidade Federal de Santa Maria (UFSM) |
repository.mail.fl_str_mv |
ouvidoria@ufsm.br |
_version_ |
1808854727742455808 |