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An unusual four-step cascade reaction for accessing furo[3,4-c]pyridine-1,4-diones via rhodium catalysis

文献类型：期刊论文

作者Li, Yidi1,5; Xu, Huiying3; Zhou, Zhi3; Huang, Lin2,4; Tang, Zhenhao4; Yi, Wei3; Wu, Xiaowei1,2,4,5
刊名ORGANIC CHEMISTRY FRONTIERS
出版日期2023-08-15
页码7
ISSN号2052-4129
DOI10.1039/d3qo00909b
通讯作者Zhou, Zhi(zhouzhi@gzhmu.edu.cn) ; Yi, Wei(yiwei@gzhmu.edu.cn) ; Wu, Xiaowei(wuxiaowei@simm.ac.cn)
英文摘要The development of efficient cascade reactions is highly important and appealing because of their desirable step-economy and convenience in constructing multiple chemical bonds and complex molecules in one shot. Herein, we report a rare four-step tandem reaction between acrylamides and 4-hydroxy-2-alkynoates to prepare novel furo[3,4-c]pyridine-1,4-diones which are difficult to synthesize by traditional methods. This unique domino reaction includes C-H activation, Lossen rearrangement, annulation, and lactonization. Additionally, this protocol features good functional group tolerance, obtainment of products by simple filtration, room temperature, and air compatibility. DFT calculations were conducted to shed some light on the reaction mechanism.
WOS关键词C-H ACTIVATION ; PROPARGYL ALCOHOLS ; GROUP MIGRATION ; BOND ; ANNULATION ; BENZAMIDES ; ALKYNES ; AMIDE ; CYCLIZATION ; AMIDATION
资助项目Basic and Applied Basic Research Foundation of Guangdong Province[2021A1515110468] ; Shanghai Pujiang Program[21PJ1415800] ; Natural Science Foundation of Guangdong Province[2019A1515010935] ; High-level New Ramp;D Institute[2019B090904008] ; High-level Innovative Research Institute[2021B0909050003] ; NSFC[21877020] ; NSFC[22007020]
WOS研究方向Chemistry
语种英语
WOS记录号WOS:001047921900001
出版者ROYAL SOC CHEMISTRY
源URL[http://119.78.100.183/handle/2S10ELR8/306920]  
专题中国科学院上海药物研究所
通讯作者Zhou, Zhi; Yi, Wei; Wu, Xiaowei
作者单位1.Chinese Acad Sci, Shanghai Inst Mat Med, Drug Discovery & Dev Ctr, Shanghai 201203, Peoples R China
2.Southern Med Univ, Sch Pharmaceut Sci, Guangzhou 510515, Peoples R China
3.Guangzhou Med Univ, Affiliated Hosp 5, Sch Pharmaceut Sci, State Key Lab Resp Dis,Guangzhou Municipal & Guang, Guangzhou 511436, Guangdong, Peoples R China
4.Chinese Acad Sci, Zhongshan Inst Drug Discovery, Shanghai Inst Mat Med, Zhongshan 528400, Peoples R China
5.Univ Chinese Acad Sci, 19A Yuquan Rd, Beijing 100049, Peoples R China
推荐引用方式
GB/T 7714		 Li, Yidi,Xu, Huiying,Zhou, Zhi,et al. An unusual four-step cascade reaction for accessing furo[3,4-c]pyridine-1,4-diones via rhodium catalysis[J]. ORGANIC CHEMISTRY FRONTIERS,2023:7.
APA Li, Yidi.,Xu, Huiying.,Zhou, Zhi.,Huang, Lin.,Tang, Zhenhao.,...&Wu, Xiaowei.(2023).An unusual four-step cascade reaction for accessing furo[3,4-c]pyridine-1,4-diones via rhodium catalysis.ORGANIC CHEMISTRY FRONTIERS,7.
MLA Li, Yidi,et al."An unusual four-step cascade reaction for accessing furo[3,4-c]pyridine-1,4-diones via rhodium catalysis".ORGANIC CHEMISTRY FRONTIERS (2023):7.

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来源：上海药物研究所

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