Synthesis of new derivatives of 1,3,4-thiadiazole and 1,3,4-oxadiazole on cyclic imides and studying their antioxidant

Abstract

The research resulted in the production of new thiadiazole derivatives and oxadiazole derivatives via the reaction of cyclic imides with chloro acetyl chloride at heat condition to give N-acetyl chloro cyclic imides (1,2). Then react these compounds (1,2) with hydrazine hydrate to give N-(aceto hydrazide) cyclic imides (3,4). Then, compounds (3,4) go into three routes: route one was reacting with CS2 in the presence of (KOH) in ethanol at (24 hrs.) to give (N-[(2-thio-1,3,4-thiadiazolo-5-yl) methylene] cyclic imides) (5,6). Route two was reacting using various aromatic carboxylic acids in the presence of (POCl3) to give (N- [{2-(subs. benzene)-1,3,4-oxadiazolo-5-yl. methylene] cyclic imides) (7-14). Route three was reacting with ammonium thiocyanate in the presence of HCl in ethanol for (5 hrs.), followed cyclization in the presence of concentration (H2SO4) to give (N-[(2-amino-1,3,4-thiadiazolo-5-yl) methylene] cyclic imides) (15,16). Prepared compounds have been characterized by FTIR, and some of them by 1H-NMR, melting point, and were studied the effects of the preparing compounds on antioxidant.