Citation: Zhang Zhu, Li Jiazhu, Wang Xinyue, Ma Jihua, Wang Xu, Wang Jinjun. Nitration (Nitroalkylation) of Pheophorbide and Synthesis of Chlorophyllous Chlorin Derivatives[J]. Chinese Journal of Organic Chemistry, ;2020, 40(9): 2895-2903. doi: 10.6023/cjoc202004054 shu

Nitration (Nitroalkylation) of Pheophorbide and Synthesis of Chlorophyllous Chlorin Derivatives

Zhang Zhu ¹ ,
Li Jiazhu ² ,
Wang Xinyue ² ,
Ma Jihua ² ,
Wang Xu ² ,
Wang Jinjun ^1,2,,

a.
Department of Food & Biological Engineering, Wenjing College, Yantai University, Yantai, Shandong 264005
b.
College of chemistry and chemical engineering, Yantai University, Yantai, Shandong 264005

Corresponding author: Wang Jinjun, wjj1955@163.com
Received Date: 30 April 2020
Revised Date: 31 May 2020
Available Online: 11 June 2020
Fund Project: the National Natural Science Foundations of China 21272048Project supported by the National Natural Science Foundations of China (No. 21272048) and the Natural Science Foundation of Shandong Province (No. ZR2015BQ012)the Natural Science Foundation of Shandong Province ZR2015BQ012

Figures(6)

Pyropheophorbide-a methyl ester was used as a starting material, and the chemical modification was carried out making use of its active groups attached to the chlorin periphery to establish the formyl group, ketene and α-diketone moieties around the N²¹-N²³ axis. The nitrations or nitroalkylations at 3-, 12-, 20-position and on the exocyclic ring were performed by the electrophilic substitution on the aromatic macrocyclic chromophore, Henry reaction at the active carbonyl groups, and Michael addition to the β-keto ester and the ketene structures on the exocyclic ring as different donor-acceptor. A series of unreported nitro(nitroalkyl) substituted chlorins related to chlorophyll were synthesized and their chemical structures were characterized by elemental analysis, UV-Vis, IR and ¹H NMR spectra.
- chlorophyll,
- pheophorbide,
- chlorin,
- nitration(nitroalkylation) reaction,
- synthesis
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