Síntese de 1,1,1-trifluoro-4-metoxi-3-alquen-2-onas funcionalizadas e 1,2-azóis derivados

• Autor(a) principal: Kuhn, Bruna Pereira
• Data de Publicação: 2014
• Tipo de documento: Dissertação
• Idioma: por
• Título da fonte: Manancial - Repositório Digital da UFSM
• dARK ID: ark:/26339/00130000149cx
• Texto Completo: http://repositorio.ufsm.br/handle/1/10587
• topic: 4,5-diidropirazóis; Pirazóis; 4,5-diidroisoxazóis; 4,5-dihydropyrazoles; Pyrazoles; 4,5-dihydroisoxazoles; CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA

This work describes the application of the method of trifluoroacetic anhydride acetal acylation to four new functionalized ketones: 6-methyl-5-hepten-2-one, 4-phenyl-4- oxobutanoic acid (3-benzoylpropionic acid), 5-bromo-2-acetylthiophene and 2- propionylthiophene. The acylated products were obtained as β-trifluoromethyl ketones alkoxyvinyl and β-diketones. The product derived from 2-propionylthiophene was obtained as dihydrate, 3,3-dihydroxy-4,4,4-trifluoro-1-(2-thienyl)-2-butanone, its structure was confirmed by X-ray diffraction crystallography. The acylated dielectrophilic precursors were cyclized with dinucleophiles hydroxylamine, hydrazine, semicarbazide and thiosemicarbazide to form the corresponding 5-trifluoromethyl-4,5-dihydroisoxazoles, 5-trifluoromethyl-4,5-dihydro-1H-pyrazoles and trifluoromethyl-1H-pyrazole in good yields (>80%). The molecular structure of the synthesized products were assigned based on the data of 1H NMR, 13C and X-ray diffraction.