Synthesis, Reactions and Antioxidant Activity of 5-(3', 4'-dihydroxy-tetrahydrofuran-2'-yl)-2-methyl-3-carbohydrazide

Abstract

In this manuscript, we describe the synthesis of the carbohydrazide 2. Acid-catalyzed condensation with several carbonyl compounds to afford the corresponding carbohydrazide derivatives 3-12. Their acetylation afforded the corresponding acetyl derivatives 13-22. Oxidative cyclization of O-acetyl derivatives 19-22 afforded the corresponding 1,3,4-oxadiazole derivatives 23-26. On the other hand, condensation of the dicarbonyl compound 27 with several aroylhydrazines to give the corresponding bisaroylhydrazones 28-32 cyclization of 28-31 afforded 1,3,4-oxadiazoles 33-36. The structures of the prepared compounds were confirmed by 1HNMR 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
• 1, 3, 4-oxadiazoles