Divergent Construction of Azaheterocycles via Alkoxyl Radical-Triggered C–C Bond Cleavage/Cyclization of <i>N</i>-Functionalized Acrylamides
Yingjie Ma, Zi-Hang Yuan, Pin Gao, Xin‐Hua Duan, Hong Xin, Le Liu, Li‐Na Guo
Abstract
An array of redox-neutral alkylation/cyclization cascade reactions of N -functionalized acrylamides with cycloalkyl hydroperoxides were achieved via the alkoxyl radical-triggered C–C bond cleavage. Through adjusting the radical acceptors on the N atom, a variety of keto-alkylated chain-containing azaheterocycles, including indolo[2,1- a ]isoquinolin-6(5 H )-ones, quinoline-2,4-diones, and pyrido[4,3,2- gh ]phenanthridines were constructed by a one-pot procedure with good yields and excellent functional group tolerance.
Topics & Concepts
ChemistryAlkylationQuinolineAlkoxy groupCleavage (geology)Bond cleavageRadical cyclizationRedoxMedicinal chemistryOrganic chemistryAlkylMaterials scienceCatalysisFracture (geology)Composite materialCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsOxidative Organic Chemistry Reactions