Visible Light-Enhanced [3 + 2] Cycloaddition of <i>N</i>,<i>N</i>-Disubstituted Hydrazines with Organo-Cyanamides: Access to Polysubstituted 1,2,4-Triazol-3-amines
Xiaoya Zhuo, Lvyin Zheng, Yujie Liu, Yihan Wang, Xiaoying Zou, Yumei Zhong, Wei Guo
Abstract
Visible light-enhanced [3 + 2] cycloaddition of N, N -disubstituted hydrazines with N -cyano- N -aryl- p -toluenesulfonamides is an efficient reaction pathway to polysubstituted 1,2,4-triazol-3-amines. The reaction is performed under mild conditions without the addition of any transition metals. This strategy involves a C(sp 3 )–H bond activation, a cyano cycloaddition, and the formation of two new C═N bonds. The protocol shows the advantages of good functional group tolerance and broad substrate scope. The late-stage modification experiments provide practical applications in the field of organic synthesis and medicinal chemistry.
Topics & Concepts
CycloadditionChemistrySubstrate (aquarium)Functional groupArylCombinatorial chemistryVisible spectrumReaction conditionsMedicinal chemistryOrganic chemistryCatalysisMaterials scienceOptoelectronicsPolymerGeologyAlkylOceanographyCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsSulfur-Based Synthesis Techniques