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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| Format: | Article |
| Language: | English |
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Science Press
2023-11-01
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| Series: | National Science Open |
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| Online Access: | https://www.sciengine.com/doi/10.1360/nso/20230019 |
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| author | Yu Feng Liu Chong Tan Fenghua Liao Yuhe Wang Liang Li Yuping Xiao Feng-Shou |
| author_facet | Yu Feng Liu Chong Tan Fenghua Liao Yuhe Wang Liang Li Yuping Xiao Feng-Shou |
| author_sort | Yu Feng |
| collection | DOAJ |
| description | 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. |
| format | Article |
| id | doaj-art-e18c70ace72e433ba31aee2e29a2944c |
| institution | OA Journals |
| issn | 2097-1168 |
| language | English |
| publishDate | 2023-11-01 |
| publisher | Science Press |
| record_format | Article |
| series | National Science Open |
| spelling | doaj-art-e18c70ace72e433ba31aee2e29a2944c2025-08-20T02:02:04ZengScience PressNational Science Open2097-11682023-11-01210.1360/nso/20230019eb33e642Sustainable production of value-added N-heterocycles from biomass-derived carbohydrates via spontaneous self-engineeringYu Feng0Liu Chong1Tan Fenghua2Liao Yuhe3Wang Liang4Li Yuping5Xiao Feng-Shou6["Key Lab of Applied Chemistry of Zhejiang Province, Department of Chemistry, Zhejiang University, Hangzhou 310028, China","Key Lab of Biomass Chemical Engineering of Ministry of Education, College of Chemical and Biological Engineering, Zhejiang University, Hangzhou 310027, China"]["State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou 350002, China"]["Guangzhou Institute of Energy Conversion, Chinese Academy of Sciences, Guangzhou 510640, China"]["Guangzhou Institute of Energy Conversion, Chinese Academy of Sciences, Guangzhou 510640, China"]["Key Lab of Biomass Chemical Engineering of Ministry of Education, College of Chemical and Biological Engineering, Zhejiang University, Hangzhou 310027, China"]["Guangzhou Institute of Energy Conversion, Chinese Academy of Sciences, Guangzhou 510640, China"]["Key Lab of Applied Chemistry of Zhejiang Province, Department of Chemistry, Zhejiang University, Hangzhou 310028, China","Key Lab of Biomass Chemical Engineering of Ministry of Education, College of Chemical and Biological Engineering, Zhejiang University, Hangzhou 310027, China"]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.https://www.sciengine.com/doi/10.1360/nso/20230019Keywords: biomass conversionsustainabilitygreen chemistrycarbohydrate<italic>N</italic>-heterocycle |
| spellingShingle | Yu Feng Liu Chong Tan Fenghua Liao Yuhe Wang Liang Li Yuping Xiao Feng-Shou Sustainable production of value-added N-heterocycles from biomass-derived carbohydrates via spontaneous self-engineering National Science Open Keywords: biomass conversion sustainability green chemistry carbohydrate <italic>N</italic>-heterocycle |
| title | Sustainable production of value-added N-heterocycles from biomass-derived carbohydrates via spontaneous self-engineering |
| title_full | Sustainable production of value-added N-heterocycles from biomass-derived carbohydrates via spontaneous self-engineering |
| title_fullStr | Sustainable production of value-added N-heterocycles from biomass-derived carbohydrates via spontaneous self-engineering |
| title_full_unstemmed | Sustainable production of value-added N-heterocycles from biomass-derived carbohydrates via spontaneous self-engineering |
| title_short | Sustainable production of value-added N-heterocycles from biomass-derived carbohydrates via spontaneous self-engineering |
| title_sort | sustainable production of value added n heterocycles from biomass derived carbohydrates via spontaneous self engineering |
| topic | Keywords: biomass conversion sustainability green chemistry carbohydrate <italic>N</italic>-heterocycle |
| url | https://www.sciengine.com/doi/10.1360/nso/20230019 |
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