Premium
Synthesis of Derivatives of Chlorines Related to Chlorophyll‐ a by Vilsmeier Reaction with Methyl Pyropheophorbide‐ a
Author(s) -
Wang JinJun,
Wu XuRan,
Shim YoungKey
Publication year - 2005
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.200500138
Subject(s) - chemistry , chlorin , nickel , acrolein , organic chemistry , phosphoryl chloride , medicinal chemistry , chloride , formylation , photochemistry , photodynamic therapy , catalysis
From methyl pyropheophorbide‐ a (MPP a , 1 ), the vinyl group was converted into other functional groups including 2‐dimethoxylethyl, 1‐hydroxylalkyl, and alkylcarbonyl groups by addition and oxidization to form chlorin ( 2˜5b ). The nickel complexes ( 6a˜e ) were prepared by treatment with excess nickel acetate in MeOH by refluxing and were used directly for the next reaction without further separation. The Vilsmeier reactions of nickel chlorins with 3‐(dimethylamino)acrolein/phosphoryl chloride (3‐DMA/POCl 3 ) are carried out to give meso ‐20‐fotmyl‐vinylpyropheophorbide‐ a ( 7a˜9b ).