Citation: Shaomin Chen, Tianjian Zhang, Zhenhua Xu, Bo You, Minghao Li, Yanlong Gu. 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[J]. Chinese Chemical Letters, ;2023, 34(9): 108130. doi: 10.1016/j.cclet.2023.108130 shu

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

Shaomin Chen ^a ,
Tianjian Zhang ^a ,
Zhenhua Xu ^a ,
Bo You ^a ,
Minghao Li ^{a, *,} ,
Yanlong Gu ^{a, b, c, *,}

a.
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
b.
School of Chemistry and Chemical Engineering, The Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, Shihezi University, Shihezi 832004, China
c.
State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Lanzhou 730000, China

liminghaochem@hust.edu.cn

klgyl@hust.edu.cn

Received Date: 12 October 2022
Revised Date: 26 December 2022
Accepted Date: 2 January 2023
Available Online: 5 January 2023

Figures(4)

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.
- Lewis acid catalysis,
- 2-Arylglycerol derivative,
- 1, 3-Biselectrophile,
- Six-membered heterocycles,
- [3+3] cyclization
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