I<sub>2</sub>‐Promoted <i>sp</i><sup>3</sup> C−H Oxidation/Annulation Sequences for the Synthesis of Indoloquinolines from 2‐(1<i>H</i>‐indol‐2‐yl)anilines and Aryl Methyl Ketones
Mariyaraj Arockiaraj, Venkatachalam Rajeshkumar
Abstract
Abstract An iodine/DMSO‐promoted approach has been developed for the synthesis of indoloquinolines via a sequential sp 3 C−H oxidation/intramolecular cyclization using 2‐(1 H ‐indol‐2‐yl)anilines and aryl methyl ketones. A wide range of aryl methyl ketones, including drugs and complex bioactive molecule‐derived substrates were compatible in the present reaction with yields in the range of 30–96%. This protocol proceeds through sp 3 C−H oxidation of aryl methyl ketones to phenylglyoxals, subsequent imine formation, and cyclization to furnish the indoloquinolines. Further, the reaction is applicable for gram‐scale synthesis and is operationally simple.
Topics & Concepts
ChemistryAnnulationArylMethyl KetoneOrganic chemistryMedicinal chemistryCombinatorial chemistryCatalysisAlkylCatalytic C–H Functionalization MethodsOxidative Organic Chemistry ReactionsNanomaterials for catalytic reactions