Hydroxymethylation of quinolines <i>via</i> iron promoted oxidative C–H functionalization: synthesis of arsindoline-A and its derivatives
Bangarigalla Shantharjun, Damera Vani, Ramanjaneyulu Unnava, Mummadi Sandeep, K. Rajender Reddy
Abstract
Herein, we report a mild and efficient hydroxymethylation of quinolines via an iron promoted cross-dehydrogenative coupling reaction under external acid free conditions. Various hydroxyalkyl substituted quinolines were achieved in excellent yields with well tolerated functional groups. Importantly, a few of the hydroxylmethylated quinolines were further transformed into respective aldehydes, and were successfully utilized for the synthesis of alkaloid arsindoline-A and its derivatives.
Topics & Concepts
Surface modificationCombinatorial chemistryChemistryOxidative phosphorylationBiochemistryPhysical chemistryCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsAsymmetric Hydrogenation and Catalysis