SYNTHESIS OF HYDRAZIDES AND THIOSEMICARBAZIDES OF AMINO CARBOXYLIC ACIDS

According to the literature derivatives of hydrazides and thiosemicarbazides aminocarboxylic acids include compounds exhibiting a different biological activity. In the present work, in order to synthesize the starting synthons - methyl 3-(2-diethylamino) ethoxy)-2-metilpropanate (III) and methyl 2-methyl-3-(2-piperidine-1-yl) ethoxy)propanate (IV) carried out reaction of aminoalcohols (I, II) with methyl methacrylate. Hydrazinolysis of synthesized carboxylic acids esters (III, IV) led to 3-(2-(diethylamino)ethoxy)-2-methylpropanehydrazide (V) and 2-methyl-3-(2-(piperidin-1-yl) ethoxy) propanehydrazide (VI). During the interaction of hydrazides (V, VI) with phenyl isothiocyanate were obtained 3-(2-diethylamino) ethoxy)-2-methyl-N'-(phenylcarbonthiol)propanehydrazide (VII) and 2-methyl-N`-(phenylcarbonthiol)-3- (2-(piperidin-1-yl) ethoxy) propanehydrazide (VIII). The structure of the obtained compounds established by IR and NMR spectroscopy. Purity of the synthesized was confirmed by TLC. Determined physicochemical properties of the final products of the reactions. Developed methods of synthesis of new aminocarboxylic acids derivatives may be used in preparative organic chemistry for synthesis of aliphatic and heterocyclic biological substances.