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Rhodium-catalyzed regioselective C-H activation/Lossen rearrangement/annulation for the green synthesis of trisubstituted 2-pyridones

文献类型：期刊论文

作者Li, Yidi1,6; Xu, Huiying3,4; Huang, Lin2,5; Zhou, Zhi3,4; Tang, Zhenhao2; Meng, Haifang2; Zhang, Wei2; Yi, Wei3,4; Wu, Xiaowei1,2,5,6
刊名ORGANIC CHEMISTRY FRONTIERS
出版日期2023-06-13
卷号10期号:12页码:3000-3009
ISSN号2052-4129
DOI10.1039/d3qo00469d
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Multisubstituted 2-pyridones are prevalent in pharmaceuticals and bioactive molecules. We herein report an efficient and regioselective approach for the synthesis of trisubstituted 2-pyridone derivatives by a rhodium-catalyzed C-H activation/Lossen rearrangement/cyclization cascade reaction between acrylamides and propargyl alcohols. The desirable features of this protocol include a reusable catalytic system, high regioselectivity, uncommon Lossen rearrangement, good functional group tolerance, operation at room temperature, simple purification by filtration in most cases, and scale-up synthesis with as low as 1 mol% catalyst loading. Additionally, deuterium labeling and KIE assays were performed to investigate the reaction mechanism. The vital effect of the hydroxyl group on propargyl alcohols in determining the regioselectivity was demonstrated by control experiments and DFT calculations. In addition, Mulliken atomic charge analysis of the key intermediates was also carried out to probe the origin of the observed preference for the Lossen rearrangement.
WOS关键词PROPARGYL ALCOHOLS ; OXIDATIVE ANNULATION ; BOND ; BENZAMIDES ; ALKYNES ; FUNCTIONALIZATION ; HYDROARYLATION ; ISOINDOLINONES ; ISOQUINOLONE ; PERAMPANEL
资助项目Shanghai Pujiang Program[21PJ1415800] ; Basic and Applied Basic Research Foundation of Guangdong Province[2021A1515110468] ; Natural Science Foundation of Guangdong Province[2019A1515010935] ; High-level New RD 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:000990112100001
出版者ROYAL SOC CHEMISTRY
源URL[http://119.78.100.183/handle/2S10ELR8/306520]  
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.Chinese Acad Sci, Zhongshan Inst Drug Discovery, Shanghai Inst Mat Med, Zhongshan 528400, Peoples R China
3.Guangzhou Med Univ, Sch Pharmaceut Sci, Guangzhou Municipal & Guangdong Prov Key Lab Prot, State Key Lab Resp Dis, Guangzhou 511436, Guangdong, Peoples R China
4.Guangzhou Med Univ, Affiliated Hosp 5, Guangzhou 511436, Guangdong, Peoples R China
5.Southern Med Univ, Sch Pharmaceut Sci, Guangzhou 510515, Peoples R China
6.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,Huang, Lin,et al. Rhodium-catalyzed regioselective C-H activation/Lossen rearrangement/annulation for the green synthesis of trisubstituted 2-pyridones[J]. ORGANIC CHEMISTRY FRONTIERS,2023,10(12):3000-3009.
APA Li, Yidi.,Xu, Huiying.,Huang, Lin.,Zhou, Zhi.,Tang, Zhenhao.,...&Wu, Xiaowei.(2023).Rhodium-catalyzed regioselective C-H activation/Lossen rearrangement/annulation for the green synthesis of trisubstituted 2-pyridones.ORGANIC CHEMISTRY FRONTIERS,10(12),3000-3009.
MLA Li, Yidi,et al."Rhodium-catalyzed regioselective C-H activation/Lossen rearrangement/annulation for the green synthesis of trisubstituted 2-pyridones".ORGANIC CHEMISTRY FRONTIERS 10.12(2023):3000-3009.

入库方式： OAI收割

来源：上海药物研究所

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