Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (11): 2099-2107.DOI: 10.6023/cjoc201206021 Previous Articles     Next Articles



杨泽a, 王振a, 徐希森a, 刘洋a, 祁彩霞b, 王进军a,b   

  1. a 烟台大学化学化工学院 烟台 264005;
    b 山东省黄金工程技术研究中心(工业应用) 烟台 264005
  • 收稿日期:2012-06-19 修回日期:2012-07-16 发布日期:2012-07-28
  • 通讯作者: 王进军
  • 基金资助:

    中匈政府间科技合作(No. 2008-333-4-32 )和山东黄金工程技术研究中心(2011年度)资助项目.

Synthesis of Chlorins with Chlorophyllous Chromophore Fused with Nitrogenous Heterocycle

Yang Zea, Wang Zhena, Xu Xisena, Liu Yanga, Qi Caixiab, Wang Jinjuna,b   

  1. a College of Chemistry and Chemical Engineering, Yantai University, Yantai 264005;
    b Shandong Applied Research Centre of Gold Nanotechnology (Au-SDARC), Yantai 264005
  • Received:2012-06-19 Revised:2012-07-16 Published:2012-07-28
  • Supported by:

    Project supported by the Project of Technology Cooperation between Governments of China and Hungary, and the Project of Shandong Applied Research Centre of Gold Nanotechnology (2011).

Methyl 132-oxopyropheophorbide-a was prepared using one pot method from chlorophyll-a, and subsequently reacted with o-diaminobenzene to produce four chlorins fused with nitrogenous heterocycle derivatives. The hyperactive functional groups such as formyl and formymethyl groups were introduced at 3-position by oxidation with thallium nitrate or osmium tetroxide. Friedländer condensation of C3-formymethyl group with o-aminobenzaldehyde was carried out smoothly to build quinolinic structure. The five-membered heterocyclic rings were established at 3-position via the 1,3-dipolar cycloaddition reaction of C3-vinyl group with diazomethane and benzonitrile oxide. The structures of new chlorins with chlorophyllous basic skeleton were characterized by UV, IR, 1H NMR and elemental analysis.

Key words: chlorophyll, chlorin, chlorin fused with nitrogenous heterocycle, synthesis