Elemental Sulfur and Dimethyl <scp>Sulfoxide‐Promoted</scp> Oxidative Cyclization of Trifluoroacetimidohydrazides with Methylhetarenes for the Synthesis of <scp>3‐Hetaryl</scp>‐5‐trifluoromethyl‐1,2,4‐triazoles
Jiajun Zhang, Jianhua Tang, Zhengkai Chen, Xiao‐Feng Wu
Abstract
Main observation and conclusion A metal‐free approach for the synthesis of 3‐hetaryl‐5‐trifluoromethyl‐1,2,4‐triazoles via sulfur/dimethyl sulfoxide‐promoted oxidative cyclization of readily available trifluoroacetimidohydrazides with methylhetarenes has been developed. This transformation proceeds in cascade sulfur‐mediated generation of thioaldehyde, condensation, intramolecular cyclization and oxidative aromatization sequence.
Topics & Concepts
ChemistryDimethyl sulfoxideAromatizationSulfurSulfoxideOxidative phosphorylationTrifluoromethylIntramolecular forceCondensationTransformation (genetics)Organic chemistryMedicinal chemistryCatalysisBiochemistryThermodynamicsPhysicsGeneAlkylFluorine in Organic ChemistrySynthesis and Biological EvaluationCyclopropane Reaction Mechanisms