Single‐Step Sustainable Production of Hydroxy‐Functionalized 2‐Imidazolines from Carbohydrates

Manufacturing valuable N‐containing chemicals from biomass is highly desirable yet challenging. Herein, a novel strategy was developed for efficient production of 2‐(1‐hydroxyethyl)‐imidazoline (HI), a high‐value and versatile building block for synthesizing a myriad of bioactive targets, directly from carbohydrates under mild reaction conditions. With this strategy, bio‐based HI was produced from fructose in one step with as high as 77 C % isolated yield in the presence of ethylenediamine (EDA) and InCl 3 at 130 °C. The synergistic functions of EDA and InCl 3 were identified for the transformation, wherein EDA promoted the scission of C−C bond of fructose backbone via retro‐aldol (R−A) reaction and rapidly trapped in‐situ formed reactive carbonyl‐containing C 3 intermediate for HI formation to avoid undesired side reaction, and InCl 3 facilitated the formation of this C 3 intermediate and the final 1,2‐hydrid shift step.