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Recent Advances in the Denitrogenative Annulation Reactions of 1,2,3‐Thiadiazoles

Марина А. Токарева, Т. В. Глухарева, Sinead T. Keaveney

2024ChemCatChem11 citationsDOIOpen Access PDF

Abstract

Abstract 1,2,3‐Thiadiazoles exhibit versatile reactivity due to their ability to undergo ring cleavage, forming α‐diazothione species through a Dimroth‐type equilibrium. Denitrogenation of the α‐diazothione, induced by high temperature, irradiation, or strong bases, allows generation of a wide range of reactive intermediates. Since 2016, the transition‐metal‐catalyzed denitrogenative transannulation of 1,2,3‐thiadiazoles has garnered significant attention as a promising approach to constructing diverse heterocyclic scaffolds. This review focuses on the denitrogenative reactions of 1,2,3‐thiadiazoles, particularly highlighting the novel rhodium‐catalyzed denitrogenative transannulation transformations along with their mechanisms.

Topics & Concepts

ThiadiazolesAnnulationReactivity (psychology)ChemistryRhodiumRing (chemistry)CatalysisCombinatorial chemistryCleavage (geology)Medicinal chemistryOrganic chemistryMaterials scienceComposite materialMedicineAlternative medicineFracture (geology)PathologyCatalytic C–H Functionalization MethodsCyclopropane Reaction MechanismsSynthesis and Biological Evaluation