Oxidative Cyclization of Trifluoroacetimidohydrazides with D‐Glucose for the Metal‐Free Synthesis of 3‐Trifluoromethyl‐1,2,4‐Triazoles
Shu‐Ning Lu, Hefei Yang, Jiajun Zhang, Zhengkai Chen, Xiao‐Feng Wu
Abstract
Abstract A metal‐free oxidative cyclization of readily available trifluoroacetimidohydrazides with D‐glucose for the assembly of 3‐trifluoromethyl‐1,2,4‐triazoles has been disclosed. D‐glucose is applied as C1 synthon to provide methine source in the reaction. Control experiments have been conducted to shed light on the reaction mechanism. The synthetic utility of the protocol has been explored by the implementation of scale up reaction and the synthesis of the key skeleton of NK I ‐receptor ligand. magnified image
Topics & Concepts
SynthonChemistryTrifluoromethylCombinatorial chemistryLigand (biochemistry)Oxidative phosphorylationStereochemistryOrganic chemistryReceptorBiochemistryAlkylFluorine in Organic ChemistrySynthesis and Biological EvaluationClick Chemistry and Applications