Synthesis and Transforming of 3-cyclohexyl-4-formylsydnone N-(2’,3’,4’,6’-tetra-O-acetyl-β-D glucopyranosyl)thiosemicarbazone Compound from Cyclohexylamine

Abstract

The thiosemicarbazone compound (6) contains sydnone ring, was synthesized from 4-formylsydnone (4), derived from cyclohexylamine (1), via four reaction series, by microwave irradiation method with 85%-yield. From the thiosemicarbazone compound (6), we performed cyclization reaction of thioure group with ethyl bromoacetate, in ethanol solvent and sodium acetate catalyst for 46 hrs to obtain thiazolidine-4-one (7) with 68%-yield. Cyclization reaction of imine group with acetic anhydride, in dichloromethane solvent for 48 hrs gave 4,5-dihydro-1,3,4-thiadiazole compound (8) with 60%-yield. Complex-formation reaction of thiosemicarbazone (6) with zinc acetate at room temperature, in a solvent of ethanol, for 3 hours yielded bis[thiosemicarbazonato]zinc(II) complex (9) with 80%-yield. Structures of thiosemicarbazone derivatives (6), thiazolidin-4-one (7), 4,5-dihydro-1,3,4-thiadiazole (8) and bis[thiosemicarbazonato]zinc(II) complex (9) was confirmed by modern spectroscopic methods (IR, ¹H & ¹³C NMR and MS). 

Keywords

Thiosemicarbazone, thiazolidin-4-one, 1,3,4- thiadiazole

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