Síntese e identificação de tiazolidinonas derivadas da 3-picolilamina e de tiazinanonas derivadas da 1-(2–aminoetil) piperidina

Abstract

This work presents the synthesis of 1,3-thiazolidin-4-ones: a) by conventional thermal heating through multicomponent reaction between 3- (aminomethyl)pyridine (3-picolylamine), fifteen arenealdehydes (R-PhCHO, where R= 2-NO2, 3-NO2, 4-NO2, 2-F, 3-F, 4-F, 2-Cl, 4-Cl, 2-OCH3, 3-OCH3, 4- OCH3, 4-CH3, 2-OH, 3-OH e 4-OH) and mercaptoacetic acid for four hours in refluxing toluene with yields 59 to 97%; b) by ultrasound through multicomponent one-pot reaction between 3-(aminomethyl)pyridine (3- picolylamine), six arenealdehydes (R-PhCHO, where R= 4-NO2, 4-F, 4-Cl, 4- OCH3, 4-CH3 e 4-OH) and mercaptoacetic acid for ten minutes in toluene with yields 30 to 78%. This work also presents the synthesis of 1,3-thiazinan-4-ones: a) by conventional thermal heating through multicomponent one-pot reaction between 2-(aminoethyl)piperidine, nineteen arenealdehydes (R-PhCHO, where R= 3- NO2, 4-NO2, 2-F, 3-F, 4-F, 2-Cl, 4-Cl, 2-OCH3, 3-OCH3, 4-OCH3, 4-CH3, 3-Cl, 2,4-Cl, 2,6-Cl, 2,3-OCH3, 2,4-OCH3, 2,5-OCH3, 3,4-OCH3 and 2-Cl,6-F) and mercaptopropionic acid for six hours in refluxing toluene with yields 38 to 99%; b) by ultrasound through multicomponent reaction between 2- (aminoethyl)piperidine, nineteen arenealdehydes (R-PhCHO, where R= 3-NO2, 4-NO2, 2-F, 3-F, 4-F, 2-Cl, 4-Cl, 2-OCH3, 3-OCH3, 4-OCH3, 4-CH3, 3-Cl, 2,4-Cl, 2,6-Cl, 2,3-OCH3, 2,4-OCH3, 2,5-OCH3, 3,4-OCH3 and 2-Cl,6-F) and mercaptopropionic acid for thirty minutes in toluene with yields 37 to 86%. The synthesized compounds had evaluated their melting points and were charactetized and identified by mass spectrometry and nuclear magnetic resonance spectroscopy of 1H and 13C.