Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (07): 1457-1464.DOI: 10.6023/cjoc201301044 Previous Articles     Next Articles



纪建业a, 夏尚文b, 赵丽丽b, 李家柱b, 祁彩霞c, 王进军b,c   

  1. a 通化师范学院化学系 通化 134002;
    b 烟台大学化学化工学院 烟台 264005;
    c 山东省黄金工程技术研究中心(工业应用) 烟台 264005
  • 收稿日期:2013-01-18 修回日期:2013-03-01 发布日期:2013-03-15
  • 通讯作者: 王进军
  • 基金资助:

    国家自然科学基金(No. 21272048)和山东省黄金工程技术研究中心(2011年度)资助项目.

Chemical Reaction of Purpurin-18 Imide and Synthesis of Chlorins Related to Chlorophyll

Ji Jianyea, Xia Shangwenb, Zhao Lilib, Li Jiazhub, Qi Caixiac, Wang Jinjunb,c   

  1. a Department of Chemistry, College of Teacher, Tonghua 134002;
    b College of Chemistry and Chemical Engineering, Yantai University, Yantai 264005;
    c Shandong Applied Research Centre of Gold Nanotechnology (Au-SDARC), Yantai 264005
  • Received:2013-01-18 Revised:2013-03-01 Published:2013-03-15
  • Supported by:

    Project supported by the National Natural Science Foundations of China (No. 21272048) and the Project of Shandong Applied Reaearch Centre of Gold Nanotechnology (2011).

Purpurin-18 imide methyl ester was used as a starting material, and its chemical reactions, including the electrophilic addition and 1,3-polar cycloaddition on the vinyl group at 3-position, the electrophilic substitution at 20-meso-position, the allomerization of C(12)-methyl group and nucleophilic substitution, were carried out making use of the chemical reactivities on the chlorin macrocycle. The different chemical structures and substituent groups were established and introduced at C(3)-, C(12)-and C(20)-meso-potation on the periphery of purpurin-18 imide. The synthesis of 11 unreported chlorins related to chlorophyll was accomplished and their chemical structures were characterized by UV, 1H NMR, IR spectra and elemental analysis. The possible mechanisms about corresponding reactions were tentatively proposed.

Key words: chlorophyll-a, purpurin-18 imide, chlorin, chemical reaction, synthesis