Synthesis and transforming of 3-cyclohecxyl-4-formylsydnone N-(2’,3’,4’,6’-tetra-O-acetyl-β-D-glucopyranosyl)thiosemicarbazon compound from cyclohexynlamine

The thiosemicarbazone compound (6) contains heterocyclic sydnone, was synthesized from cyclohexylamine (1) by microwave irradiation method, yield 85%. From the thiosemicarbazone compound (6), we performed cyclization reaction of thioure group with ethyl bromoacetate, in ethanol solvent and sodium acetate catalyst, in 46 hours, obtained the thiazolidine-4-one (7), yield 68%. When performing the cyclization reaction of imine group with acetic anhydride, in dichloromethane solvent, in 46 hours, obtained 4,5-dihydro-1,3,4-thiadiazol derivatives (8), yield 60%. For thiosemicarbazone (6) reacts with zinc acetate at room temperature, in a solvent of ethanol, about 3 hours, obtained the bis [thiosemicarbazonato] zinc(II) complex (9), yield 80%. Structures of thiosemicarbazone derivatives (6), thiazolidin-4-on (7), 4,5-dihydro-1,3,4-thiadiazole (8) and bis[thiosemicarbazonato]zinc(II) complex (9) was confirmed by infrared spectrum, nuclear magnetic resonance spectrum and mass spectrometry method.