A Metal‐ and Azide‐free Oxidative Coupling Reaction for the Synthesis of [1,2,3]Triazolo[1,5‐a]quinolines and their Application to Construct C−C and C‐P Bonds, 2‐Cyclopropylquinolines and Imidazo[1,5‐a]quinolines
Zhi‐Hao Shang, Zhen‐Xiao Zhang, Wei‐Zhao Weng, Yufei Wang, Tian‐Wei Cheng, Qiuyi Zhang, Liqun Song, Tian‐Qi Shao, Kai‐Xuan Liu, Yanping Zhu
Abstract
Abstract An iodine‐promoted one‐pot cascade oxidative annulation reaction has been developed for the synthesis of [1,2,3]triazolo[1,5‐a]quinolines from methyl azaarenes and N ‐tosylhydrazines. The reaction has a broad substrate scope and can be easily scaled up to gram‐scale. 1,2,3‐Triazoles are an important skeletal structure for the construction of C−C and C−P bonds, 2‐cyclopropylquinolines and imidazo[1,5‐a]quinolines, for which different synthetic applications were explored. magnified image
Topics & Concepts
ChemistryAnnulationAzideCombinatorial chemistryOxidative coupling of methaneCascade reactionSubstrate (aquarium)StereochemistryCoupling reactionIodineOxidative phosphorylationMedicinal chemistryOrganic chemistryCatalysisBiochemistryGeologyOceanographyClick Chemistry and ApplicationsCyclopropane Reaction MechanismsCatalytic C–H Functionalization Methods