具有氮杂环并叶绿素色基结构的二氢卟吩衍生物的合成
收稿日期: 2012-06-19
修回日期: 2012-07-16
网络出版日期: 2012-07-28
基金资助
中匈政府间科技合作(No. 2008-333-4-32 )和山东黄金工程技术研究中心(2011年度)资助项目.
Synthesis of Chlorins with Chlorophyllous Chromophore Fused with Nitrogenous Heterocycle
Received date: 2012-06-19
Revised date: 2012-07-16
Online published: 2012-07-28
Supported by
Project supported by the Project of Technology Cooperation between Governments of China and Hungary, and the Project of Shandong Applied Research Centre of Gold Nanotechnology (2011).
杨泽 , 王振 , 徐希森 , 刘洋 , 祁彩霞 , 王进军 . 具有氮杂环并叶绿素色基结构的二氢卟吩衍生物的合成[J]. 有机化学, 2012 , 32(11) : 2099 -2107 . DOI: 10.6023/cjoc201206021
Methyl 132-oxopyropheophorbide-a was prepared using one pot method from chlorophyll-a, and subsequently reacted with o-diaminobenzene to produce four chlorins fused with nitrogenous heterocycle derivatives. The hyperactive functional groups such as formyl and formymethyl groups were introduced at 3-position by oxidation with thallium nitrate or osmium tetroxide. Friedländer condensation of C3-formymethyl group with o-aminobenzaldehyde was carried out smoothly to build quinolinic structure. The five-membered heterocyclic rings were established at 3-position via the 1,3-dipolar cycloaddition reaction of C3-vinyl group with diazomethane and benzonitrile oxide. The structures of new chlorins with chlorophyllous basic skeleton were characterized by UV, IR, 1H NMR and elemental analysis.
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