Regio- and stereoselective N2-functionalization with propanamide fragment of aromatic and heteroaromatic aldehydes thiosemicarbazones

Abstract

Aiming at the synthesis of new potentially pharmacologically active compounds combining in the molecule structures of thiosemicarbazone and 3-hydrazinylpropionic acid, we performed a regio- and stereoselective N²-functionalization of thiosemicarbazones of aromatic and heteroaromatic aldehydes by alkaline hydration of the corresponding (E)-N²-cyanoethyl derivatives (propanenitriles) prepared by a regioand stereoselective cyanoethylation with acrylonitrile. The hydration proceeds with the retention of the Econfiguration of the initial propanenitriles.