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

doi:10.6023/cjoc201301044

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

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红紫素-18二酰亚胺的化学反应及其叶绿素类二氢卟吩衍生物的合成

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

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 E-mail:wjj1955@163.com
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 Jianye^a, Xia Shangwen^b, Zhao Lili^b, Li Jiazhu^b, Qi Caixia^c, Wang Jinjun^b,c

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

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]. Chin. J. Org. Chem., 2013, 33(07): 1457-1464.

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红紫素-18二酰亚胺的化学反应及其叶绿素类二氢卟吩衍生物的合成

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

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