3,4-(metilenodioxi)anilina como precursor para a síntese de tiazolidinonas.

Abstract

This work describes and discusses the synthesis of novel twenty two 2-aryl-3- (benzo[d][1,3]dioxol-5-yl)thiazolidin-4-ones by conventional heating method. The compounds were obtained through a one-pot reaction of 3,4-(methylenedioxy)aniline, mono and disubstituted (o, m, p) arenaldehydes with electron donating (OCH3, OH, CH3) or electron withdrawing (NO2, F, Cl) groups and the mercaptoacetic acid. The reaction was carried out refluxing toluene for 22 hours in a Dean-Stark trap. Under these conditions, the products were obtained as solids or dense oils with 47-90% yields after purification. Using this methodology, the spirothiazolidinone from cyclohexanone was synthesized in 68% yield. All thiazolidinones were fully identified and characterized by Mass Spectrometry and Nuclear Magnetic Resonance of Hydrogen and Carbon.