Synthesis and intramolecular cyclization of thiosemicarbazide morpholilacetic acid

Abstract

The paper gives details on the synthesis of four new, potentially biologically active compounds based on amorpholineheterocycle structure. By alkylation of morpholine with ethyl bromoacetate, a morfolilacetic acid ethyl ester was synthesized. Its reaction with hydrazine hydrate led to the hydrazide. We developed the method for synthesis and studied cyclization of thiosemicarbazide morfolilaceticacidin in alkaline medium with formation of bisgeterocyclic system. The possibility of the existence of this compound in two tautomeric forms: thione and thiol, i.e. a 3- (1'-morpholyl-methyl) -1,2,4-triazole-5-thione and 3- (1-morpholyl-1'-methyl) -5-mercapto-1,2,4-triazole was described. In neutral medium, one product was obtained. According to spectral data, it is attributed to the structure of 3-(1'-morpholil-methyl)-1,2,4-triazole-5-thione. Structure of newly synthesized compounds is confirmed by IR and ¹H-NMR spectra and data of elemental analysis. These compounds are potentially biologically active substances and are promising for further research.