Rearrangement Reactions of Pyropheophorbide with Diazoalkane and Synthesis of Chlorophyll Derivatives

doi:10.6023/cjoc201804048

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (11): 2993-3001.DOI: 10.6023/cjoc201804048 Previous Articles Next Articles

Special Issue: 有机小分子-金属协同催化

Articles

焦脱镁叶绿酸与重氮烷的重排反应及其叶绿素衍生物的合成

张珠^a, 徐希森^b, 李彦龙^b, 李家柱^b, 王进军^a,b

a 烟台大学文经学院食品与生物工程系烟台 264005;
b 烟台大学化学化工学院烟台 264005

收稿日期:2018-04-30 修回日期:2018-06-16 发布日期:2018-07-24
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.21272048）和山东省高校科技计划（No.J15LC51）资助项目.

Rearrangement Reactions of Pyropheophorbide with Diazoalkane and Synthesis of Chlorophyll Derivatives

Zhang Zhu^a, Xu Xisen^b, Li Yanlong^b, Li Jiazhu^b, Wang Jinjun^a,b

a Department of Food & Biological Engineering, Wenjing College, Yantai University, Yantai 264005;
b College of Chemistry and Chemical Engineering, Yantai University, Yantai 264005

Received:2018-04-30 Revised:2018-06-16 Published:2018-07-24
Supported by:
Project supported by the National Natural Science Foundations of China (No. 21272048) and the University Science and Technology Plan Projects of Shandong Province (No. J15LC51).

1. Rearrangement Reactions of Pyropheophorbide with Diazoalkane and Synthesis of Chlorophyll Derivatives.PDF(281KB)

Abstract

Pyropheophorbide-a methyl ester and its derivatives acidylated and alkenylated along the N²¹-N²³ axis were used as starting materials. The 1,3-dipolar cyclocaddition, Michael addition and Tiffeneau-Demjanov rearrangement reaction can smoothly occur with diazoalkane through the carbon-oxygen or carbon-carbon double bonds attached to the periphery to generate new heterocyclic and carbonylic structures in different positions. The synthesis of a series of unreported chlorins related to chlorophyll was accomplished and their chemical structures were characterized by elemental analysis, UV-Vis, IR, MS and ¹H NMR spectra. Meanwhile, the region-and stereo-selectivities of rearrangement processes were discussed based on relevant reaction mechanism.

Key words: chlorophyll-a, chlorin, pyropheophorbide, diazoalkane, rearrangement reaction

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Zhang Zhu, Xu Xisen, Li Yanlong, Li Jiazhu, Wang Jinjun. Rearrangement Reactions of Pyropheophorbide with Diazoalkane and Synthesis of Chlorophyll Derivatives[J]. Chin. J. Org. Chem., 2018, 38(11): 2993-3001.

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焦脱镁叶绿酸与重氮烷的重排反应及其叶绿素衍生物的合成

Rearrangement Reactions of Pyropheophorbide with Diazoalkane and Synthesis of Chlorophyll Derivatives

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