Synthesis of Benzimidazolo-Fused Purpurin-18 Derivatives with the Basic Skeleton of Chlorophyll

doi:10.6023/cjoc1107064

Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (02): 318-325 .DOI: 10.6023/cjoc1107064 Previous Articles Next Articles

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具有叶绿素基本碳架的苯并咪唑并红紫素-18 衍生物的合成

刘冉冉^a, 王鲁敏^a, 殷军港^a, 武进^b, 刘超^b, 张朋^b, 王进军^a

a 烟台大学化学化工学院烟台 264005;
b 烟台大学药学院烟台 264005

收稿日期:2011-07-06 修回日期:2011-09-08 发布日期:2012-03-09
通讯作者: 王进军 E-mail:wjj1955@163.com
基金资助:
山东省自然科学基金(No. Y2008B49)资助项目.

Synthesis of Benzimidazolo-Fused Purpurin-18 Derivatives with the Basic Skeleton of Chlorophyll

Liu Ranran^a, Wang Lumin^a, Yin Jungang^a, Wu Jin^b, Liu Chao^b, Zhang Peng^b, Wang Jinjun^a

a College of Chemistry and Chemical Engineering, Yantai University, Yantai 264005;
b Pharmacy College, Yantai University, Yantai 264005

Received:2011-07-06 Revised:2011-09-08 Published:2012-03-09
Supported by:
Project supported by the Natural Science Foundation of Shandong Province (No. Y2008B49).

The condensation and rearrangement reactions of methyl pheophorbide-a with 1,2-benzenediamine afforded benzimidazolo[ 2,1-n]purpurin-18 methyl ester, benzimidazolo[1,2-o]purpurin-18 methyl ester, quinoxalino[2,3-n]-deoxopyropheophorbide- a methyl ester and chlorine-p₆ trimethyl ester. The syntheses of benzimidazol-fused chlorins with the basic skeleton of chlorophyll were carried out by fluorination, chlorination, bromination and iodonation for 20-meso-position and allomerization for methyl group at 12-position. The structures of new chlorophyll derivatives were characterized by UV, IR, ¹H NMR, MS spectra and elemental analysis.

Key words: chlorophyll-a, methyl pheophorbide-a, benzimidazol-fused chlorin, chemical modification

Cite this article

Liu Ranran, Wang Lumin, Yin Jungang, Wu Jin, Liu Chao, Zhang Peng, Wang Jinjun. Synthesis of Benzimidazolo-Fused Purpurin-18 Derivatives with the Basic Skeleton of Chlorophyll[J]. Chin. J. Org. Chem., 2012, 32(02): 318-325 .

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具有叶绿素基本碳架的苯并咪唑并红紫素-18 衍生物的合成

Synthesis of Benzimidazolo-Fused Purpurin-18 Derivatives with the Basic Skeleton of Chlorophyll

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