Metal-free [2 + 1 + 3] Cycloaddition of Trifluoroacetaldehyde <i>N</i>-Sulfonylhydrazones with Hexahydro-1,3,5-triazines Leading to Trifluoromethylated 2,3,4,5-Tetrahydro-1,2,4-triazines
Zhongxue Fang, Qihao Jin, Xinyu Wang, Yongquan Ning
Abstract
A transition-metal-free [2 + 1 + 3] cycloaddition of trifluoroacetaldehyde N-sulfonylhydrazone and hexahydro-1,3,5-triazine was described. This operationally simple protocol provides a general synthesis of diverse trifluoromethylated 2,3,4,5-tetrahydro-1,2,4-triazines in 81–97% yield with a broad substrate scope, including aryl, benzyl, and alkyl hexahydro-1,3,5-triazine.
Topics & Concepts
CycloadditionChemistryYield (engineering)TriazineArylAlkylSubstrate (aquarium)MetalTransition metalMedicinal chemistryOrganic chemistryCombinatorial chemistryCatalysisEcologyMaterials scienceMetallurgyBiologyFluorine in Organic ChemistrySynthesis and Biological EvaluationCyclopropane Reaction Mechanisms