A Lewis acid-catalyzed tandem reaction enabling 2-arylglycerol derivative as a versatile 1,3-biselectrophile for the synthesis of 4H-chromenes and 2-pyridinones |
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| Institution: | 1. Key Laboratory for Large-Format Battery Materials and System, Ministry of Education, Hubei Key Laboratory of Material Chemistry and Service Failure, School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, Wuhan 430074, China;2. School of Chemistry and Chemical Engineering, The Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, Shihezi University, Shihezi 832004, China;3. State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Lanzhou 730000, China;1. School of Pharmacy and Pharmaceutical Science & Institute of Materia Medica, Shandong First Medical University & Shandong Academy of Medical Sciences, NHC Key Laboratory of biotechnology drug (Shandong Academy of Medical Sciences), Key Lab for Rare & Uncommon Diseases of Shandong Province, Ji''nan 250117, China;2. School of Chemistry and Chemical Engineering, Shandong University, Ji''nan 250100, China;1. Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry; School of Future Technology, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Beijing 100190, China;2. Key Laboratory of Bio-inspired Materials and Interfacial Science, Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190, China;3. Research Center of Chiral Drugs, Innovation Research Institute of Traditional Chinese Medicine, Shanghai University of Traditional Chinese Medicine, Shanghai 200438, China;1. School of Petrochemical Engineering, Changzhou University, Changzhou 213164, China;2. Department of Chemistry, Maynooth University, National University of Ireland, Maynooth, Co. Kildare, Ireland;3. State Key Laboratory of Analytical Chemistry for Life Science, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, China;1. Liaoning & Shenyang Key Laboratory of Functional Dye and Pigment, Shenyang University of Chemical Technology, Shenyang 110142, China;2. Department of Cell Biology, China Medical University, Shenyang 110122, China;3. State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 110624, China;4. Department of Chemistry, Graduate School of Science, Hiroshima University, Higashi-Hiroshima 7398526, Japan;1. State Key Laboratory of Advanced Technology for Materials Synthesis and Processing, Wuhan University of Technology, Wuhan 430070, China;2. Hubei Key Laboratory of Low Dimensional Optoelectronic Materials and Devices, Hubei University of Arts and Science, Xiangyang 441053, China;3. Hubei Institute of Aerospace Chemotechnology, Xiangyang 441003, China;4. Hubei Longzhong Laboratory, Xiangyang 441000, China;1. Hengyang Medical School, University of South China, Hengyang 421001, China;2. School of Chemistry and Chemical Engineering, University of South China, Hengyang 421001, China |
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| Abstract: | Acid-catalyzed tandem reactions were established by employing a novel class of 2-arylglycerol derivative, 5-aryl-1,3-dioxan-5-ol, as versatile 1,3-biselectrophile. In the reactions, 5-aryl-1,3-dioxan-5-ol works like atropaldehydes or 2-aryl malondialdehydes, and can react with 2-naphthols and β-keto amides, allowing the synthesis of 4H-chromenes and 5-aryl-2-pyridinones. High yields, good functional group tolerance, broad substrate scope and simple reaction operation make this protocol attractive. |
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