Synthesis of C-3-Pyrazolinyl-substituted Chlorins Related to Chloro-phyll-a

Chin. J. Org. Chem. ›› 2011, Vol. 31 ›› Issue (08): 1213-1221. Previous Articles Next Articles

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C3-吡唑啉基取代的叶绿素类二氢卟吩衍生物的合成

殷军港¹，李韵伟¹，李家柱¹，张千¹，裴文²，王进军*^,1

(¹烟台大学化学化工学院烟台 264005)
(²浙江工业大学绿色化学合成技术国家重点实验室培育基地杭州 310032)

收稿日期:2011-01-11 修回日期:2011-03-07 发布日期:2011-03-21
通讯作者: 王进军 E-mail:wjj1955@163.com

Synthesis of C-3-Pyrazolinyl-substituted Chlorins Related to Chloro-phyll-a

Yin Jungang¹ Li Yunwei¹ Li Jiazhu¹ Zhang Qian¹ Pei Wen² Wang Jin-jun*^,1

(¹ Colledge of Chemistry and Chemical Engineering, Yantai University, Yantai 264005)
(² State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Zhejiang University of Technology, Hangzhou 310032)

Received:2011-01-11 Revised:2011-03-07 Published:2011-03-21

Abstract

Methyl pheophorbide-a was used as starting material and modified for the E-ring, the carbon-carbon double bands at 3-position and 20-meso-hydrogen to construct and introduce different functional groups on the chlorin chromophore. The synthesis of a series of C-3-pyrazolinyl-substituted chlorins related to chlorophyll-a was fulfilled by the 1,3-dipolar cyclocaddition of the C-3-vinyl groups with diazomethane. The region- and stereo-selectiveties in 1,3-dipolar cyclocaddition of the chlorins were discussed. The struc-tures of new chlorophyll derivatives were characterized by UV, IR, ¹H NMR spectra and elemental analysis.

Key words: chlorophyll-a, chlorine, methyl pheophorbide-a, chemical modification, 1,3-dipolar cyclocaddition

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YIN Jun-Gang, LI Yun-Wei, LI Jia-Zhu, ZHANG Qian, PEI Wen, WANG Jin-Jun. Synthesis of C-3-Pyrazolinyl-substituted Chlorins Related to Chloro-phyll-a[J]. Chin. J. Org. Chem., 2011, 31(08): 1213-1221.

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C3-吡唑啉基取代的叶绿素类二氢卟吩衍生物的合成

Synthesis of C-3-Pyrazolinyl-substituted Chlorins Related to Chloro-phyll-a

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