Natl Sci Open
Volume 2, Number 6, 2023
|Number of page(s)
|01 November 2023
Sustainable production of value-added N-heterocycles from biomass-derived carbohydrates via spontaneous self-engineering
Key Lab of Applied Chemistry of Zhejiang Province, Department of Chemistry, Zhejiang University, Hangzhou 310028, China
2 Key Lab of Biomass Chemical Engineering of Ministry of Education, College of Chemical and Biological Engineering, Zhejiang University, Hangzhou 310027, China
3 State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou 350002, China
4 Guangzhou Institute of Energy Conversion, Chinese Academy of Sciences, Guangzhou 510640, China
Revised: 3 July 2023
Accepted: 5 July 2023
Synthetic N-heterocyclic compounds, such as quinoxalines, have shown a crucial role in pharmaceutical as well as food and dye industries. However, the traditional synthesis toward N-heterocycles relies on multistep energy and cost-intensive non-sustainable processes. Here, we report a facile approach that allows one-step conversion of biomass-derived carbohydrates to valuable quinoxalines in the presence of aryl-1,2-diamines in water without any harmful metal catalysts/organic solvents via spontaneously engineering involved cascade reactions under hydrothermal conditions. Aryl-1,2-diamines are revealed as the key to propel this transformation through boosting carbohydrate fragmentation into small 1,2-dicarbonyl intermediates and subsequently trapping them for constituting stable quinoxaline scaffolds therefore avoiding a myriad of undesired side reactions. The tunability of product selectivity can be also achievable by adjusting the basicity of the reaction environment. Both batch and continuous-flow integrated processes were verified for production of quinoxalines in an exceptionally eco-benign manner (E-factor <1), showing superior sustainability and economic viability.
Key words: biomass conversion / sustainability / green chemistry / carbohydrate / N-heterocycle
© The Author(s) 2023. Published by Science Press and EDP Sciences
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