Radziszewski-Type Oxidation of 3,5-di(α-cyanostyryl)-1,2,4-thiadiazoles

Abstract

Due to the presence of two acrylonitrile fragments, 3,5-di(α-cyanostyryl)-1,2,4-thiadiazoles are prone to react under Radziszewski reaction conditions (oxidative hydrolysis of nitriles to amides) with the simultaneous epoxidation and formation of epoxyamides. We found that the reaction proceeds in a non-selective way and yields a mixture of products of regioisomeric oxidation. Only in one case we succeeded to isolate the product of double epoxidation. The structure of the epoxyamides products was confirmed by IR and NMR spectroscopy data.

Keywords

• arylmethylene cyanothioacetamides
• 1,2,4-thiadiazoles
• Radziszewski oxidation
• epoxyamides