有机化学 ›› 2017, Vol. 37 ›› Issue (9): 2336-2342.DOI: 10.6023/cjoc201703004 上一篇    下一篇

研究论文

钯催化[2+2+2]环化反应制备5,6-二氢苯并菲啶衍生物

吴玉芹, 于凉云, 张奇, 李立冬   

  1. 盐城工学院化学化工学院 盐城 224051
  • 收稿日期:2017-03-02 修回日期:2017-03-30 出版日期:2017-09-25 发布日期:2017-05-10
  • 通讯作者: 李立冬 E-mail:ld-l@163.com
  • 基金资助:

    国家自然科学基金(No.21272005)资助项目.

Synthesis of Dihydrophenanthridines by Palladium-Catalyzed[2+2+2] Cyclization Reactions

Wu Yuqin, Yu Liangyun, Zhang Qi, Li Lidong   

  1. School of Chemistry and Chemical Engineering, Yancheng Institute of Technology, Yancheng 224051
  • Received:2017-03-02 Revised:2017-03-30 Online:2017-09-25 Published:2017-05-10
  • Contact: 10.6023/cjoc201703004 E-mail:ld-l@163.com
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21272005).

菲啶骨架化合物是一类重要的有机分子并广泛存在于天然产物中,也是一类重要的抗菌抗癌的生物活性分子.通过钯催化二炔和芳卤经[2+2+2]环化加成反应,发展了一种高效实用的制备二氢菲啶衍生物的Domino方法.所合成目标产物的结构经IR、1H NMR、13C NMR和HRMS表征确证,其中7,12-二苯基-5-对甲苯磺酰基-5,6-二氢苯并[j]菲啶-10-乙酮(3b)的结构还通过X射线单晶衍射分析确认.

关键词: 钯催化, 合成, C-C偶联, 二氢菲啶

Phenanthridines are important core structures found in a variety of natural products and other biologically important molecules with a wide range of biological activities and applications, including antibacterial and anticancer agents. A practical and efficient domino method for the preparation of dihydrophenanthridines from diynes and aryl halides is developed via palladium-catalyzed[2+2+2] cycloaddition reactions. All new products were fully characterized by IR, 1H NMR, 13C NMR and high-resolution mass spectrometry. The molecular structure of 1-(7,12-diphenyl-5-tosyl-5,6-dihydrobenzo[j]-phenanthridin-10-yl)ethan-1-one (3b) was confirmed by using single-crystal X-ray analyses.

Key words: palladium-catalyzed, synthesis, C-C coupling, dihydrophenanthridine