Electrocatalytic Three-Component Reaction: Synthesis of Cyanide-Functionalization Imidazo-Fused N-Heterocycles

Abstract

An electrochemical three-component cyclization was developed under metal-free conditions, which provides a novel and facile approach for the construction of cyanide-functionalization imidazo-fused N-heterocycles. A variety of cyanide-functionalization imidazo-fused N-heterocycles can be obtained from easily available methyl Nheteroaromatics, primary alkylamines, and trimethylsilyl cyanide with good to excellent yields. The reaction features a broad scope of substrates, scalability, and mild conditions.

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

“…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 . Inspired by these studies and our previous works, herein, we disclosed the electrochemical oxidative transformation of aryl ketones with benzylamines into 1,2,4-trisubstituted-(1 H )-imidazoles under transition-metal and oxidant-free conditions.…”

Multicomponent reactions and photo/electrochemistry join forces: atom economy meets energy efficiency

“…In 2019, Qian et al reported the electrocatalytic synthesis of imidazo-fused N-heterocycles from 2-methylquinolines via reaction with benzylamines and TMSCN in the presence of ammonium iodide (Scheme 122). 229 The formation of the key imine intermediate starts from the isomerization of 2methylquinoline to 2-methylene-1,2-dihydroquinoline, which readily reacted with the anodically formed molecular iodide to give 2-(iodomethyl)quinoline. Nucleophilic substitution by the benzylamine, followed by oxidation, provides the imine intermediate.…”

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

“…This reaction also provided a practical protocol for the synthesis of polysubstituted oxazoles. The proposed mechanism involves the reaction of electrogenerated The same group [37] utilized the same hybrid-electrocatalytic methodology this time for the synthesis of cyanide-functionalized imidazo[1,5-a]quinolones (Scheme 26). This three-component cyclization reaction was achieved by the reaction between 2-methylquinolines, primary alkyl amines along with Trimethylsilyl cyanide (TMSCN)as cyanide source at 90°C in an undivided cell.…”