Electrochemically initiated intermolecular C–N formation/cyclization of ketones with 2-aminopyridines: an efficient method for the synthesis of imidazo[1,2-a]pyridines

Abstract

Electrochemical intermolecular C–N formation for the synthesis of imidazopyridines.

Electrochemical HI-mediated Intermolecular C–N Bond Formation to Synthesize Imidazoles from Aryl Ketones and Benzylamines

“…On the other hand, the electrochemical-promoted formation of the C–N bond for the synthesis of heterocyclic compounds such as imidazoles is extremely limited. Yu developed an electrochemically mediated synthesis of imidazo­[1,2- a ]­pyridines from acetophenones, unsaturated, and alkyl ketones with 2-aminopyridines through the intermolecular C–N bond formation . Wang reported an electrochemical tandem cyclization for the construction of imidazo­[1,5- a ]­quinolines in the presence of iodine .…”

Recent Advances in the Synthesis of Imidazo[1,2‐a]pyridines: A Brief Review

“…Several intramolecular electrochemically oxidative aminations of alkenes, alkynes, arenes and alkanes have been reported for the formation of N ‐heterocycles [146] . To explore an efficient environmentally‐friendly electrochemical method, Feng et al [147] . developed a metal‐free intermolecular C−N formation cyclization for the formation of imidazo[1,2‐ a ]pyridines 189 by using 2‐aminopyridine derivatives 188 and ketones 187 .…”

Electrifying Sustainability on Transition Metal‐Free Modes: An Eco‐Friendly Approach for the Formation of C−N Bonds

“…Yu and co‐workers [40] reported a methodology for the construction of imidazopyridine using HI as a source of iodide redox mediator in conjugation with electrosynthesis (Scheme 29). The incorporation of mediator in this electrocatalytic system allows selective amination of ketones with pyridine without oxidizing the labile amine group along with remarkable functional group tolerance for groups like hydroxy, nitro, cyano, ester, and halides.…”