Síntese de 4-trifluormetil-5-(propan-1-ol-3-il)-1H-piridin-2-iminas N-substituídas

Abstract

This work presents a simple and accessible synthetic route for the preparation of a series, of nineteen new N-substituted 4-trifluormethyl-5- (propan-1-ol-3-yl)-pyridin-2-(1H)-imines, obtained from the reaction between 3- (3,4-dihydro-2H-pyran-5-yl)-4,4,4-trifluorobut-2-enenitrile with the following amines: methylamine, ethylamine, propylamine, iso-propylamine, butylamine, sec-butylamine, benzylamine, phenethylamine, 2-methoxy-phenethylamine, 4- methoxy-phenethylamine, 3,4-methoxy-phenethylamine, 4-fluorophenethylamine, 2-chloro-phenethylamine, 3-chloro-phenethylamine, 4-chlorophenethylamine, 2-(1-cyclohexenyl)-ethylamine, 2-N-morpholyl-ethylamine, N,N-dimethyl-ethyl-1,2-diamine e N,N-diethyl-ethyl-1,2-diamine. The 2-pyridinimines were synthetized through a solvent free methodology and in a short reaction time. The purification step was performed with liquidliquid extractions. After evaporation of the solvent, the product was washed with hot hexane to remove any trace of residual amine. The products were obtained with yield between 29-82%. The 2-pyridinimines obtained in this work were characterized by 1H and 13C NMR, 2D NMR, Mass Spectrometry, and Infrared Spectroscopy and their purity confirmed by Elemental Analysis and/or High Resolution Mass Spectrometry.