Chinese Journal of Organic Chemistry >
Reaction of meso-Pyropheophorbide-a and Synthesis of Chlorophyllous Chlorin Derivatives
Received date: 2013-11-23
Revised date: 2013-12-30
Online published: 2014-01-22
Supported by
Project supported by the National Natural Science Foundation of China (No. 21272048) and the Project of Shandong Applied Reaearch Centre of Gold Nanotechnology (2011).
meso-Pyropheophorbide-a methyl ester was used as a starting material, and the halogenation and nitration were carried out with different electrophilic reagents making use of active regions in chlorin macrocycle selectively to introduce chlorine, bromine, iodine and nitryl group at 20-meso-position, respectively. The reconstructions for five-membered exocyclic E-ring by allomerization and aminolysis were completed to fuse different azo-heterocycle with the exocyclic ring. The synthesis of 13 unreported chlorins related to chlorophyll was accomplished and their chemical structures were characterized by elemental analysis, UV-Vis, IR and 1H NMR spectra. The reaction mechanisms of meso-pyropheophorbide-a and corresponding spectral properties were discussed.
Key words： chlorophyll-a; chlorin; meso-pyropheophorbide; chemical reaction; synthesis
Xu Xisen , Yao Nannan , Liu Yang , Yin Jungang , Qi Caixia , Wang Jinjun . Reaction of meso-Pyropheophorbide-a and Synthesis of Chlorophyllous Chlorin Derivatives[J]. Chinese Journal of Organic Chemistry, 2014 , 34(5) : 938 -947 . DOI: 10.6023/cjoc201311039
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