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Radziszewski-type oxidation of 3,5-di(α-cyanostiryl)-1,2,4-thiadiazoles
Published:
31 October 2022
by MDPI
in The 25th International Electronic Conference on Synthetic Organic Chemistry
session General Organic Synthesis
Abstract:
Due to the presence of two acrylonitrile fragments, 3,5-di(α-cyanostiryl)-1,2,4-thiadiazoles prone to react under Radziszewski reaction conditions (oxidative hydrolysis of nitriles to amides) with simultaneous epoxidation and formation of epoxyamides. It is established that the reaction proceeds nonselectively,and gives a mixture of products of regioisomeric oxidation. Only in one of the cases, it was possible to isolate the product of double epoxidation. The structure of the epoxyamides products was confirmed by IR and NMR spectroscopy data.
Keywords: arylmethylenecyanothioacetamides, 1,2,4-thiadiazoles, Radziszewski oxidation, epoxyamides.