Copper-Mediated Cyclization of <i>o</i>-Hydroxyaryl Enaminones with 3-Indoleacetic Acids toward the Synthesis of 3-Indolmethyl-Chromones
Kangmei Wen, Yinyan Li, Qiwen Gao, Jiewen Chen, Jie Yang, Xiaodong Tang
Abstract
Here, we describe a copper-mediated tandem decarboxylative coupling/annulation protocol of o-hydroxyaryl enaminones with 3-indoleacetic acids. A series of 3-indolmethyl-chromones were afforded in up to 97% yield. A one-pot method for 3-indolmethyl-chromones from o-hydroxy acetophenones, N, N-dimethylformamide dimethyl acetal, and 3-indoleacetic acids was also developed. Derivatization of the products was conducted to provide various indolmethyl-substituted pyrimidines. Moreover, a biological evaluation revealed that some compounds had anti-influenza viral activities.
Topics & Concepts
ChemistryDerivatizationAnnulationYield (engineering)TandemOrganic chemistryDimethylformamideAcetalCopperCatalysisHigh-performance liquid chromatographySolventMaterials scienceMetallurgyComposite materialCatalytic C–H Functionalization MethodsSynthesis and Characterization of PyrrolesSynthesis of Indole Derivatives