Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (6): 1353-1356.DOI: 10.6023/cjoc201412036 Previous Articles     Next Articles



许旭升a,b, 刘志千b, 邵文浩b, 叶霁b, 孙青龑b, 何薇薇a, 张卫东a,b   

  1. a 华东理工大学药学院 上海 200237;
    b 第二军医大学药学院 上海 200433
  • 收稿日期:2014-12-20 修回日期:2015-01-28 发布日期:2015-02-10
  • 通讯作者: 张卫东
  • 基金资助:

    国家自然科学基金(81230090)、上海市重点学科建设(No. B906)资助项目.

Process Improvement on the Synthesis of Nitidine Chloride

Xu Xushenga,b, Liu Zhiqianb, Shao Wenhaob, Ye Jib, Sun Qingyanb, He Weiweia, Zhang Weidonga,b   

  1. a College of Pharmacy, East China University of Science and Technology, Shanghai 200237;
    b College of Pharmacy, The Second Military Medical University, Shanghai 200433
  • Received:2014-12-20 Revised:2015-01-28 Published:2015-02-10
  • Supported by:

    Project supported by the NSFC (No. 81230090), the Shanghai Leading Academic Discipline Project (No. B906).

Nitidine chloride was synthesized via reductive amination, intramolecular Heck coupling reaction, aromatization, methlyation and ion exchange, using 6-bromine-3,4-dimethoxybenzaldehyde and 6,7-methylenedioy-1-naphthylamine as starting material. The key intramolecular Heck coupling reaction was optimized, and acetic acid palladium(II) [Pd(OAc)2], tris(2-methylphenyl)phosphine [P(o-tol)3] and N,N-dimethylformamide (DMF) system was confirmed as the most efficient conditions. The total yield was increased significantly, and the optimal conditions may also be applied to the synthesis of other benzo[c]phenanthridine alkaloid.

Key words: nitidine chloride, intramolecular Heck reaction, synthesis