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Citation: Zhang Zhu, Xu Xisen, Li Yanlong, Li Jiazhu, Wang Jinjun. Rearrangement Reactions of Pyropheophorbide with Diazoalkane and Synthesis of Chlorophyll Derivatives[J]. Chinese Journal of Organic Chemistry, ;2018, 38(11): 2993-3001. doi: 10.6023/cjoc201804048 shu

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

Corresponding author: Wang Jinjun, wjj1955@163.com
Received Date: 30 April 2018
Revised Date: 16 June 2018
Available Online: 24 November 2018
Fund Project: 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)the University Science and Technology Plan Projects of Shandong Province J15LC51the National Natural Science Foundations of China 21272048

Figures(4)

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.
- chlorophyll-a,
- chlorin,
- pyropheophorbide,
- diazoalkane,
- rearrangement reaction
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