Synthesis of 3,5-Disubstituted-1,2,4-thiadiazoles via NaH–DMF-Promoted Dehydrogenative Intramolecular N–S Bond Formation
Mary Antony P, A.S. Jeevan Chakravarthy, Hiriyakkanavar Ila
Abstract
A facile transition-metal-free synthesis of 3,5-bis(het)aryl/arylaminothiadiazoles has been reported. The overall protocol involves base-mediated tandem thioacylation of amidines with dithioesters or aryl isothiocyanates in DMF solvent and subsequent in situ intramolecular dehydrogenative N-S bond formation of thioacylamidine intermediates under an inert atmosphere. A probable mechanism involving a carbamoyl anion, generated by deprotonation of DMF, acting as a radical initiator has been suggested.
Topics & Concepts
ChemistryDeprotonationIntramolecular forceMedicinal chemistryArylTandemThiadiazolesSolventPolymer chemistryStereochemistryOrganic chemistryIonAlkylMaterials scienceComposite materialSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization MethodsRadical Photochemical Reactions