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Chinese Journal of Organic Chemistry >

2014 , Vol. 34 >Issue 11: 2262 - 2271

DOI: https://doi.org/10.6023/cjoc201405009

ARTICLE

Hydroxyla(acyla)tion of Purpurin-18 Imide and Synthesis of Chlorophyllous Chlorin Derivatives

  • Ji Jianye ,
  • Yin Jungang ,
  • Zhao Lili ,
  • Yao Nannan ,
  • Qi Caixia ,
  • Wang Jinjun
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  • a Department of Chemistry, College of teachers, Tonghua 134002;
    b Wenjing College, Yantai University, Yantai 264005;
    c Shandong Applied Research Centre of Gold Nanotechnology (Au-SDARC), Yantai 264005

Received date: 2014-05-06

  Revised date: 2014-06-13

  Online published: 2014-09-12

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 methyl ester, as a starting material, was converted into purpurin-18 imide linked substituted structures bearing hydroxyl or acyl group at nitrogen atom in the imide by aminolysis for exocyclic ring. The hydroxyl, acyl or substituted groups with relevant functional structures were introduced by oxidation, allomerization, radical substitution and nucleophilic substitution reaction making use of active reactive regions on the periphery. The syntheses of 12 unreported chlorophyllous chlorins with carbon skeleton of purpurin-18 imide were accomplished and their chemical structures were characterized by UV, IR, 1H NMR and elemental analysis. The different effects on the tetrapyrrol macrocycle by hydroxylation and acylation are discussed.

Key words： chlorophyll-a; chlorin; purpurin-18 imide; chemical modification; synthesis

Cite this article

Ji Jianye , Yin Jungang , Zhao Lili , Yao Nannan , Qi Caixia , Wang Jinjun . Hydroxyla(acyla)tion of Purpurin-18 Imide and Synthesis of Chlorophyllous Chlorin Derivatives[J]. Chinese Journal of Organic Chemistry, 2014 , 34(11) : 2262 -2271 . DOI: 10.6023/cjoc201405009

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