Síntese de 2-(1h-pirazol-1-il)-5-(1h-pirazol-1-il-1-carbonil) piridinas

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...

Nível de Acesso:openAccess
Publication Date:2008
Main Author: Paim, Gisele Rocha lattes
Orientador/a: Bonacorso, Helio Gauze lattes
Banca: Martins, Marcos Antonio Pinto lattes, Flores, Alex Fabiani Claro lattes
Format: Dissertação
Language:por
Published: Universidade Federal de Santa Maria
Programa: Programa de Pós-Graduação em Química
Department: Química
Assuntos em Português:
Áreas de Conhecimento:
Online Access:http://repositorio.ufsm.br/handle/1/10419
Citação: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.
Resumo Português: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.
Resumo inglês: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.