Direct Electrochemical Reductive Synthesis - a Tool for Novel Classes of N-Oxy Heterocycles

Abstract

Nitrogen containing heterocycles represent an important and common structural motif in natural products and blockbuster pharmaceuticals. Thus, their synthesis plays a crucial role in the chemical industry. The N-oxy motif is commonly found as major metabolites for such nitrogen containing heterocycles. As an innovative tool, electrochemistry enables direct access to N-oxy heterocycles via direct reduction of easily accessible nitro arenes. By using electrical current from renewable resources as an inherently safe and inexpensive reagent, electrochemistry contributes to an increased sustainability of chemical processes.[1,2] A simple galvanostatic set-up in an undivided beaker-type cell with inexpensive electrolytes was used to access a broad variety of quinoline N-oxides and 1-oxy quinazolin-4-ones in up to a multi-gram scale. This toolset offers an innovative synthetic protocol for synthesizing this novel class of compounds by only using sustainable chemicals and electricity as an inherently safe reagent.[3,4]