Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (11): 2993-3001.DOI: 10.6023/cjoc201804048 Previous Articles     Next Articles

Special Issue: 有机小分子-金属协同催化



张珠a, 徐希森b, 李彦龙b, 李家柱b, 王进军a,b   

  1. a 烟台大学文经学院食品与生物工程系 烟台 264005;
    b 烟台大学化学化工学院 烟台 264005
  • 收稿日期:2018-04-30 修回日期:2018-06-16 发布日期:2018-07-24
  • 通讯作者: 王进军
  • 基金资助:


Rearrangement Reactions of Pyropheophorbide with Diazoalkane and Synthesis of Chlorophyll Derivatives

Zhang Zhua, Xu Xisenb, Li Yanlongb, Li Jiazhub, Wang Jinjuna,b   

  1. a Department of Food & Biological Engineering, Wenjing College, Yantai University, Yantai 264005;
    b College of Chemistry and Chemical Engineering, Yantai University, Yantai 264005
  • Received:2018-04-30 Revised:2018-06-16 Published:2018-07-24
  • Supported by:

    Project supported by the National Natural Science Foundations of China (No. 21272048) and the University Science and Technology Plan Projects of Shandong Province (No. J15LC51).

Pyropheophorbide-a methyl ester and its derivatives acidylated and alkenylated along the N21-N23 axis were used as starting materials. The 1,3-dipolar cyclocaddition, Michael addition and Tiffeneau-Demjanov rearrangement reaction can smoothly occur with diazoalkane through the carbon-oxygen or carbon-carbon double bonds attached to the periphery to generate new heterocyclic and carbonylic structures in different positions. The synthesis of a series of unreported chlorins related to chlorophyll was accomplished and their chemical structures were characterized by elemental analysis, UV-Vis, IR, MS and 1H NMR spectra. Meanwhile, the region-and stereo-selectivities of rearrangement processes were discussed based on relevant reaction mechanism.

Key words: chlorophyll-a, chlorin, pyropheophorbide, diazoalkane, rearrangement reaction