科研之友
微信
新浪微博
Facebook
分享链接
摘要
The rhodochlorin was synthesized by a series of degradation from pheophorbide-a. The electrophilic substitution of rhodochlorin was performed with N-chlorosuccinimide (NCS) or nitric acid as electrophilic reagent; 1,3-polar cycloaddition reactions of C-3-vinyl group of rhodochlorin with p-chlorobenzonitrile oxide or diazomethane constructed isoxazoline and pyrazoline rings on the chlorin chromophore, respectively. The pyrolysis reaction of pyrazolinesubstituted chlorin introduced cyclopropyl group at C-3-position. In acid condition rhodochlorin dimethyl was hydrolyzed to its monoester. After introducing chlorine atom at 20-meso-position the purpurin-7 trimethyl was selectively converted into monochloro-substituted rhodochlorin by decarboxylation to remove functional group at 15-position. The structures of all new compounds were characterized by elemental analysis, UV, IR and (1)H NMR spectra. In same time, the possible mechanisms in the air oxidation and rearrangement reaction were tentatively proposed.
