A convenient synthesis of 1,3,4-thiadiazole and 1,3,4-oxadiazole based peptidomimetics employing diacylhydrazines derived from amino acids

Synthesis of novel orthogonally protected 1,3,4-thiadiazole and 1,3,4-oxadiazole tethered dipeptide mimetics is described. Both the heterocycles are prepared via a set of diacylhydrazines derived from amino acids. 1,3,4-Thiadiazoles are synthesized by dehydrosulfurization using Lawesson's reagent while 1,3,4-oxadiazoles are obtained by EDC mediated cyclodehydration.

Synthesis of orthogonally protected 1,3,4-thiadiazole and 1,3,4-oxadiazole tethered dipeptide mimetics through a common intermediate, peptidyl diacylhydrazines is described. 1,3,4-Thiadiazoles are synthesized by dehydrosulfurization using Lawesson's reagent while 1,3,4-oxadiazoles are obtained by the EDC mediated cyclodehydration.