Copper‐Catalyzed Decarbonylative Cyclization of Isatins and Trifluoroacetimidohydrazides for the Synthesis of 2‐(5‐Trifluoromethyl‐1,2,4‐triazol‐3‐yl)anilines
Yu Zhang, Zuguang Yang, Zhengkai Chen, Leifang Liu, Xiao‐Feng Wu
Abstract
Abstract A copper‐catalyzed intramolecular decarbonylative cyclization reaction of isatins and trifluoroacetimidohydrazides for the synthesis of 2‐(5‐trifluoromethyl‐1,2,4‐triazol‐3‐yl)aniline derivatives has been developed. This transformation proceeds through a cascade condensation, hydrolysis, decarboxylation, and intramolecular C−N bond formation sequence. The obtained 1,2,4‐triazole products bearing a free amino group can be readily converted into other useful compounds. magnified image
Topics & Concepts
ChemistryTrifluoromethylIntramolecular forceDecarboxylationAnilineCatalysisCopperMedicinal chemistryOne-pot synthesisHydrolysisCondensationCombinatorial chemistryStereochemistryOrganic chemistryThermodynamicsPhysicsAlkylFluorine in Organic ChemistryClick Chemistry and ApplicationsCyclopropane Reaction Mechanisms