Chinese Journal of Organic Chemistry >
Heterocyclization for the Structures on the Periphery of Py-ropheophorbide and Synthesis of Chlorophyll Derivatives
Received date: 2018-06-30
Revised date: 2018-07-28
Online published: 2018-08-23
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).
In order to expand study and application for the chlorophllous chlorins, pyropheophorbide-a methyl ester was used as a starting material. The chemical modifications and structural transformations along the terminals of N21-N23 axis were carried out to build active electron-accepting functional structures such as aldehyde, α-diketone, enenitrile and ketene moieties. The cyclizations with different electron-sufficient systems were accomplished to synthesize a series of unreported chlorins related to chlorophyll with multiple heterocyclic structures. The chemical structures of new compounds were characterized by elemental analysis, MS, UV-Vis, IR and 1H NMR spectra. Meanwhile the relevant formation process of the heterocyclic ring, the stereochemistry selectivity and the change of the electronic spectrum were discussed.
Key words： chlorophyll-a; chlorin; chemical modification; heterocyclization reaction; synthesis
Zhang Zhu , Li Jiazhu , Zhang Shanguo , Wang Zhen , Wang Jinjun . Heterocyclization for the Structures on the Periphery of Py-ropheophorbide and Synthesis of Chlorophyll Derivatives[J]. Chinese Journal of Organic Chemistry, 2018 , 38(12) : 3250 -3259 . DOI: 10.6023/cjoc201806046
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