Synthesis, Reactions and Antioxidant Activity of ۵-(۳', ۴'-dihydroxy-tetrahydrofuran-۲'-yl)-۲-methyl-۳-carbohydrazide

In this manuscript, we describe the synthesis of the carbohydrazide ۲. Acid-catalyzed condensation with several carbonyl compounds to afford the corresponding carbohydrazide derivatives ۳-۱۲. Their acetylation afforded the corresponding acetyl derivatives ۱۳-۲۲. Oxidative cyclization of O-acetyl derivatives ۱۹-۲۲ afforded the corresponding ۱,۳,۴-oxadiazole derivatives ۲۳-۲۶. On the other hand, condensation of the dicarbonyl compound ۲۷ with several aroylhydrazines to give the corresponding bisaroylhydrazones ۲۸-۳۲ cyclization of ۲۸-۳۱ afforded ۱,۳,۴-oxadiazoles ۳۳-۳۶. The structures of the prepared compounds were confirmed by ۱HNMR and Mass Spectra. The mechanism of the formation of the products was discussed. Furthermore, the antioxidant activities of some of the prepared compounds were examined.

Keywords:

carbohydrazides , bisaroylhydrazones , ۱ , ۳ , ۴-oxadiazoles