KCS

Heterocyclic compounds are commonly used scaffolds on which pharmacophores are arranged to provide potent and selective drugs. This is especially true for five-membered ring heterocyclic compounds, which serve as the core components of large number substances that possess a wide range of interesting biological activities. In this family, 1,3,4-oxadiazoles and 1,3,4-thiadiazoles have been used as “privileged” scaffolds to produce substances of interest in numerous therapeutic areas, such as antiimflammatory, antimicrobial, anticonvulsant, and antihypertensive. In addition, these heterocycles serve as intermediates in the preparation of various biologically important compounds. Herein, we would like to report our finding about a selective, reagent-based method for the solid-phase synthesis of 1,3,4-oxadiazoles and 1,3,4-thiadiazoles. Resin-bound acyldithiocarbazates were reacted with p-TsCl or TMSCl to give the corresponding resin-bound 1,3,4-oxadiazoles or 1,3,4-thiadiazoles through chemoselective cyclization processes.