Synthesis of 2,1-Benzoisoxazole-Containing 1,2,3-Triazoles through Copper-Catalyzed Three-Component Domino Reactions of <i>o</i>-Bromoacetophenones, Aldehydes, and Sodium Azide
Yuwei Wang, Pei Yu, Qingyun Ren, Feng‐Cheng Jia, Yunfeng Chen, An‐Xin Wu
Abstract
We herein describe an efficient copper-catalyzed three-component domino protocol used to prepare 2,1-benzoisoxazole-containing 1,2,3-triazoles from commercially available o-bromoacetophenones, aldehydes, and sodium azide. This domino process involves Aldol condensation, copper-catalyzed azide-chalcone oxidative cyclization, 1,2,3-triazole-assisted azidation, and denitrogenative cyclization sequences. The formed compounds could be considered as benzo[c]isoxazole-functionalized combretastatin A-4 triazole analogues, which might be potential applications in the discovery of a new anticarcinogen.
Topics & Concepts
ChemistrySodium azideDominoChalconeAzideCombinatorial chemistryCatalysisTriazoleAromatizationCopperOrganic chemistryClick Chemistry and ApplicationsSynthesis and Biological EvaluationSynthesis and biological activity