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Chinese Journal of Organic Chemistry >

2012 , Vol. 32 >Issue 11: 2154 - 2161

DOI: https://doi.org/10.6023/cjoc1201202

Notes

Synthesis of 20-meso-Substituted Chlorins with the Basic Skeleton of Chlorophyll-a

  • Wang Lumin ,
  • Wang Zhen ,
  • Yang Ze ,
  • Jin Yingxue ,
  • Wang Jinjun
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  • a College of Chemistry and Chemical Engineering, Yantai University, Yantai 264005;
    b College of Chemistry and Chemical Engineering, Harbin Normal University, Harbin 150025;
    c Shandong Applied Research Centre of Gold Nanotechnology (Au-SDARC), Yantai 264005

Received date: 2012-01-20

  Revised date: 2012-07-12

  Online published: 2012-07-18

Supported by

Project supported by the National Natural Science Foundations of China (No. 20972036) and the Natural Science Foundation of Shandong Province of China (No. Y2008B49).

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Abstract

Methyl pheophorbide-a (MPa) was used as starting material. The coupling reaction of MPa with diazobenzene hydrochloride, hydrobromide and sulfate was carried out to give traces of expected product, while major products were 20-halogenated and nitroso-substituted chlorins. Zinc methyl pyropheophorbide-a reacted with 3-N,N-dimethylacrolein to give Vilsmeier product. The bromination of pyropheophorbide-d with N-bromosuccinimide (NBS) formed single 20-brominated product, the vinyl group of which was resumed by Wittig reaction to give 20-bromopyropheophorbide-a. The electrophilic substitution of other chlorphyllous degradation products afforded corresponding 20-meso-substituted chlorin derivatives in better yields, respectively. The structures of all the new chlorins with basic skeleton of chlorophyll were characterized by UV, IR, 1H NMR spectra and elemental analysis.

Key words： chlorophyll-a; pheophorbide-a; pyropheophorbide-a; chlorin; electrophilic reaction

Cite this article

Wang Lumin , Wang Zhen , Yang Ze , Jin Yingxue , Wang Jinjun . Synthesis of 20-meso-Substituted Chlorins with the Basic Skeleton of Chlorophyll-a[J]. Chinese Journal of Organic Chemistry, 2012 , 32(11) : 2154 -2161 . DOI: 10.6023/cjoc1201202

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