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

doi:10.6023/cjoc201405009

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (11): 2262-2271.DOI: 10.6023/cjoc201405009 Previous Articles Next Articles

ARTICLE

红紫素-18二酰亚胺的羟(酰)基化及其叶绿素类二氢卟吩衍生物的合成

纪建业^a, 殷军港^b, 赵丽丽^b, 姚楠楠^b, 祁彩霞^c, 王进军^b,c

a 通化师范学院化学系通化 134002;
b 烟台大学文经学院烟台 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:2014-05-06 修回日期:2014-06-13 发布日期:2014-09-12
通讯作者: 王进军,wjj1955@163.com 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.

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

Ji Jianye^a, Yin Jungang^b, Zhao Lili^b, Yao Nannan^b, Qi Caixia^c, Wang Jinjun^b,c

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:2014-05-06 Revised:2014-06-13 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).

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]. Chin. J. Org. Chem., 2014, 34(11): 2262-2271.

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红紫素-18二酰亚胺的羟(酰)基化及其叶绿素类二氢卟吩衍生物的合成

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

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