Modification for the E-Ring of 132-Oxo-pyropheophorbide-a and Synthesis of Chlorin Derivatives

doi:10.6023/cjoc1108192

Chin. J. Org. Chem. ›› 2012, Vol. ›› Issue (03): 632-638.DOI: 10.6023/cjoc1108192 Previous Articles Next Articles

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13²-氧代焦脱镁叶绿酸的E-环修饰及其二氢卟吩类衍生物的合成

邬旭然, 刘超, 杨泽, 姚楠楠, 王进军

烟台大学化学化工学院烟台 264005

收稿日期:2011-08-19 修回日期:2011-10-18 发布日期:2012-03-24
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. 20972036)、山东省自然科学基(No. Y2008B49)和中匈政府间科技合作(No. 2008-333-4-32)资助项目.

Modification for the E-Ring of 13²-Oxo-pyropheophorbide-a and Synthesis of Chlorin Derivatives

Wu Xuran, Liu Chao, Yang Ze, Yao Nannan, Wang Jinjun

College of Chemistry and Chemical Engineering, Yantai University, Yantai 264005

Received:2011-08-19 Revised:2011-10-18 Published:2012-03-24
Supported by:
Project supported by the National Natural Science Foundation of China (No. 20972036), the Natural Science Foundation of Shangdong Province of China (No. Y2008B49), and the International Science and Technology Project between Governments of China and Hungary (No. 2008-333-4-32).

The methyl 13²-oxo-pyropheophorbide-a was used as a starting material and converted quantitatively into purpourin- 18 by allomerization and rearrangement in the basic condition. Under the catalysis of BF₃, the aldol reaction of acetophenone gave 13¹-phenylacylmethylene-substituted chlorin and keto-rhodin, respectively. The Knoevenagel reaction with malononitrile, condensation with aminothiocarbamide, rearrangement with diazomethane and Grignard reaction with benzyl megnesium bromide afforded a series of chlorins possessing long wavelength absorption. 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, methyl 13²-oxo-pyropheophorbide-a, chlorin, chemical modification, synthesis

Cite this article

Wu Xuran, Liu Chao, Yang Ze, Yao Nannan, Wang Jinjun. Modification for the E-Ring of 13²-Oxo-pyropheophorbide-a and Synthesis of Chlorin Derivatives[J]. Chin. J. Org. Chem., 2012, (03): 632-638.

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13²-氧代焦脱镁叶绿酸的E-环修饰及其二氢卟吩类衍生物的合成

Modification for the E-Ring of 13²-Oxo-pyropheophorbide-a and Synthesis of Chlorin Derivatives

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132-氧代焦脱镁叶绿酸的E-环修饰及其二氢卟吩类衍生物的合成