Chinese Journal of Organic Chemistry >
Chemical Modifications of Purpurin-18 and Synthesis of Chlorophyllous Chlorins Derivatives
Received date: 2014-10-06
Revised date: 2014-12-22
Online published: 2015-01-09
Supported by
Project supported by the National Natural Science Foundations of China (No. 21272048) and the Project of Shandong Applied Reaearch Centre of Gold Nanotechnology (2011).
Purpurin-18 methyl ester and its imid ester were used as starting materials. The cycloaddition of the 3-vinyl group in purpurin-18 with nitril oxide or azomethine as 1,3-dipole was carried up to established different five-membered heterocyclic structures on the chlorin chromophore. Azadiene, prepared from the condensation of arylamine with aromatic aldehyde, with double bond at 3-position of purpurin-18 conducted hetero-Diels-Alder reaction (Povarov reaction) to generate ring-opening rearranged products substituted with aroyl or aralkyl group. The electrophilic substitution, allomerization and like-Aldol reaction were accomplished making use of the reactivity of C(12)-methyl or 20-meso-hydrogen to introduce various substitutes at 12- and 20-position on the periphery of purpurin-18. The synthesis of a series of unreported chlorins related to chlorophyll was accomplished and their chemical structures were characterized by elemental analysis, UV, IR and 1H NMR spectra. The reaction mechanisms involved were also discussed accordingly.
Key words： chlorophyll-a; chlorin; purpurin-18; chemical reaction; synthesis
Liu Hongyao , Zhu Guohua , Liu Ranran , Jin Yingxue , Qi Caixia , Wang Jinjun . Chemical Modifications of Purpurin-18 and Synthesis of Chlorophyllous Chlorins Derivatives[J]. Chinese Journal of Organic Chemistry, 2015 , 35(6) : 1320 -1329 . DOI: 10.6023/cjoc201410003
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