有机化学 ›› 2022, Vol. 42 ›› Issue (7): 2089-2097.DOI: 10.6023/cjoc202203001 上一篇    下一篇

所属专题: 有机氟化学虚拟合辑

研究论文

银催化三氟甲硫基化-环化-水解: 含F3CS基喹啉酮合成

李猛a, 孙凯b,*()   

  1. a淄博职业学院制药与生物工程系 山东淄博 255300
    b烟台大学化学化工学院 山东烟台 264005
  • 收稿日期:2022-03-01 修回日期:2022-04-03 发布日期:2022-08-09
  • 通讯作者: 孙凯
  • 基金资助:
    国家自然科学基金(21801007); 武陵山民族药解析与创制湖南省工程实验室开放基金(Hgxy2103)

Silver-Mediated Trifluoromethylthiolation-Cyclization-Hydrolysis: Access to F3CS-Containing Quinolinones

Meng Lia, Kai Sunb()   

  1. aDepartment of Pharmacy and Biotechnology, Zibo Vocational Institute, Zibo, Shandong 255300
    bCollege of Chemistry and Chemical Engineering, Yantai University, Yantai, Shandong 264005
  • Received:2022-03-01 Revised:2022-04-03 Published:2022-08-09
  • Contact: Kai Sun
  • Supported by:
    National Natural Science Foundation of China(21801007); Aid Program from Hunan Engineering Laboratory for Analyse and Drugs Development of Ethnomedicine in Wunlin Mountains(Hgxy2103)

以氰基作为自由基受体, 开发了一种实用的银催化三氟甲硫化/环化/水解策略. 在中等到较高产率的条件下, 获得了各种结构多样的F3CS-取代喹啉酮类化合物. 该方法易于放大量制备, 且产物具有进一步衍生化的潜力. 因此, 对制备其他有价值的含氟砌块的氮杂环化合物很有吸引力. 机理研究表明, 该催化体系涉及自由基途径, H2O在水解过程中起着不可或缺的作用.

关键词: 三氟甲硫基化, 氮杂环, 环化, 自由基, 衍生化

Herein, a practical formal silver-mediated trifluoromethylthiolation cyclization hydrolysis protocol was developed with the cyano group as a radical acceptor. Various structurally diverse F3CS-substituted quinolinones were obtained in moderate to high yields. Easy scale-up operation and the potential for product derivatization make this method attractive for the preparation of other valuable F3CS-containing N-heterocycles. Mechanistic studies suggest that the catalytic system involves a radical pathway and H2O plays an indispensable role in the hydrolysis process.

Key words: trifluoromethylthiolation, N-heterocycles, cyclization, radical, derivatization