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Chinese Journal of Organic Chemistry >

2013 , Vol. 33 >Issue 07: 1457 - 1464

DOI: https://doi.org/10.6023/cjoc201301044

Articles

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

  • Ji Jianye ,
  • Xia Shangwen ,
  • Zhao Lili ,
  • Li Jiazhu ,
  • Qi Caixia ,
  • Wang Jinjun
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  • 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 date: 2013-01-18

  Revised date: 2013-03-01

  Online 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).

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Abstract

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

Cite this article

Ji Jianye , Xia Shangwen , Zhao Lili , Li Jiazhu , Qi Caixia , Wang Jinjun . Chemical Reaction of Purpurin-18 Imide and Synthesis of Chlorins Related to Chlorophyll[J]. Chinese Journal of Organic Chemistry, 2013 , 33(07) : 1457 -1464 . DOI: 10.6023/cjoc201301044

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