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Lewis Acid-Catalyzed Tandem Annulation of Propargylic Alcohols with 2-Allylphenols and Their Anti-tumor Activities

文献类型： 外文期刊

作者： Li, Xiang 1 ; Guo, Ning-Yu 1 ; Liu, Qing-Hui 1 ; Han, Ya-Ping 1 ; Zhang, Hong-Yu 1 ; Peng, Li-Zeng 2 ;

作者机构： 1.Hebei Univ Technol, Sch Chem Engn & Technol, Tianjin 300130, Peoples R China

2.Shandong Acad Agr Sci, Inst Agrofood Sci & Technol, Key Lab Agroprod Proc Technol Shandong Prov, Key Lab Novel Food Resources Proc,Minist Agr, Jinan, Peoples R China

关键词： Lewis acid-catalyzed; Propargylic alcohols; 2-Allylphenols; Meyer-Schuster rearrangement; Anti-tumor activities

期刊名称：ASIAN JOURNAL OF ORGANIC CHEMISTRY （ 影响因子：2.8； 五年影响因子：2.8 ）

ISSN： 2193-5807

年卷期： 2024 年

页码：

收录情况： SCI

摘要： A novel bismuth(III) trifluoro-methanesulfonate-catalyzed and environmentally benign synthetic strategy for the construction of a wide range of structurally diverse, sophisticated [5,6,5]-oxygen-containing tricyclic frameworks with easy-to handle propargylic alcohols and 2-allylphenols as substrates in the presence of Bi(OTf)3 and AgOTf is described. This Lewis acid catalyzed [3+2] annulation protocol, which tolerates a great deal of functional groups, proceeds through a sequential Meyer-Schuster rearrangement, nucleophilic substitution, 5-exo-trig cyclization, 5-endo-trig cyclization, and proton exchange sequences, affording a versatile approach for accessing oxygen-containing tricyclic skeletons in moderate-to-excellent yields. In addition, most of the obtained compounds exhibited anti-tumor activities against three types of human cancer cell lines in vitro, including Caco-2 colon cancer cells, MCF-7 breast cancer cells, and Hepg-2 liver cancer cells. A novel strategy for the assembly of a wide range of structurally diverse, sophisticated [5,6,5]-oxygen-containing tricyclic frameworks is developed through bismuth(III) trifluoro-methanesulfonate-catalyzed [3+2] annulation protocol. Moderate-to-excellent yields are observed among different propargylic alcohols and 2-allylphenols, providing a practical approach for accessing oxygen-containing tricyclic skeletons, which exhibit anti-tumor activities against three types of human cancer cell lines. image

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