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 InCl3 at 130 degrees C. The synergistic functions of EDA and InCl3 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 InCl3 facilitated the formation of this C-3 intermediate and the final 1,2-hydrid shift step.

Automated summary

A novel strategy was developed for efficient production of 2-(1-hydroxyethyl)-imidazoline (HI) directly from carbohydrates under mild reaction conditions, achieving a high isolated yield. The synergistic functions of ethylenediamine (EDA) and InCl3 were identified for the transformation, promoting the scission of C-C bond of fructose backbone and facilitating the formation of reactive intermediates for HI production.