Sustainable production of value-added N-heterocycles from biomass-derived carbohydrates via spontaneous self-engineering
Abstract: 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 faci...
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| Main Authors: | , , , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
Science Press
2023-11-01
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| Series: | National Science Open |
| Subjects: | |
| Online Access: | https://www.sciengine.com/doi/10.1360/nso/20230019 |
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| Summary: | Abstract: 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. |
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| ISSN: | 2097-1168 |