Synthesis of Chlorins with Chlorophyllous Chromophore Fused with Nitrogenous Heterocycle

doi:10.6023/cjoc201206021

Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (11): 2099-2107.DOI: 10.6023/cjoc201206021 Previous Articles Next Articles

Articles

具有氮杂环并叶绿素色基结构的二氢卟吩衍生物的合成

杨泽^a, 王振^a, 徐希森^a, 刘洋^a, 祁彩霞^b, 王进军^a,b

a 烟台大学化学化工学院烟台 264005;
b 山东省黄金工程技术研究中心(工业应用) 烟台 264005

收稿日期:2012-06-19 修回日期:2012-07-16 发布日期:2012-07-28
通讯作者: 王进军 E-mail:wjj1955@163.com
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

Yang Ze^a, Wang Zhen^a, Xu Xisen^a, Liu Yang^a, Qi Caixia^b, Wang Jinjun^a,b

a College of Chemistry and Chemical Engineering, Yantai University, Yantai 264005;
b Shandong Applied Research Centre of Gold Nanotechnology (Au-SDARC), Yantai 264005

Received:2012-06-19 Revised:2012-07-16 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).

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.

Key words: chlorophyll, chlorin, chlorin fused with nitrogenous heterocycle, synthesis

Cite this article

Yang Ze, Wang Zhen, Xu Xisen, Liu Yang, Qi Caixia, Wang Jinjun. Synthesis of Chlorins with Chlorophyllous Chromophore Fused with Nitrogenous Heterocycle[J]. Chin. J. Org. Chem., 2012, 32(11): 2099-2107.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Kozyrev, A. N.; Chen, Y.-H.; Goswami, L. N.; Tabaczynski, W. A.; Pandey, P. K. J. Org. Chem. 2006, 71, 1949.

[2] Lash, T. D. J. Porphyrins Phthalocyanines 2011, 15, 1093.

[3] Springer, J. W.; Faries, K. M.; Diers, J. R.; Muthiah, C.; Mass, O.; Kee, H. L.; Kirmaier, C.; Jonathan S.; Lindsey, J. S.; Bocian, D. F.; Dewey Holten, D. Photochem. Photobiol. 2012, 88, 651.

[4] Wang, J.-J. Chin. J. Org. Chem. 2005, 25, 1353 (in Chinese).

(王进军, 有机化学, 2005, 25, 1353.)

[5] (a) Jinadasa, R. G. W.; Hu, X.-K.; Vicente, M, G.; Smith, K. M. J. Med. Chem. 2011, 54, 7464.

(b) Kunieda, M.; Tamiaki, H. J. Org. Chem. 2008, 73, 7686.

(c) Goswami, L. N.; Ethirajan, M.; Dobhal, M. P.; Zhang, M.; Missert, J. R.; Shibata, M.; Kadish, K. M.; Pandey, R. K. J. Org. Chem. 2009, 74, 568.

(d) Wu, J.; Yin, J.-G.; Liu, R.-R.; Yang, Z.; Wang, Z.; Wang, J.-J. Chin. J. Org. Chem. 2012, 32, 149 (in Chinese).

(武进, 殷军港, 刘冉冉, 杨泽, 王振, 王进军, 有机化学, 2012, 32, 149.)

[6] (a) Li, J.-Z.; Wang, J.-J.; Yoon, I.; Cui, B.-C.; Shim, Y. K. Bioorg. Med. Chem. Lett. 2012, 22, 1846.

(b) Yin, J.-G.; Wang, Z.; Yang, Z.; Liu, C.; Wang, J.-J. Chin. J. Org. Chem. 2012, 32, 360 (in Chinese ).

(殷军港, 王振, 杨泽, 刘超, 王进军, 有机化学, 2012, 32, 360.)

[7] Smith, K. M.; Gogg, D. A.; Simpson, D. J. J. Am. Chem. Soc. 1985, 107, 4946.

[8] Wang, J.-J.; Han, G.-F.; Wu, X.-R.; Shim, Y.-J. Chin. J. Org. Chem. 2005, 25, 101 (in Chinese).

(王进军, 韩光范, 邬旭然, 沈荣基, 有机化学, 2005, 25, 101.)

[9] Kozyrev, A. N.; Suresh, V.; Das, S.; Senge, M. O.; Shibata, M.; Dougherty, T. J.; Pandey, R. K. Tetrahedron 2000, 56, 3353.

[10] Ji, J.-Y.; Li, J.-Z.; Wang, H.; Li, F.-G.; Hang, G.-F.; Shim, Y.-K.; Wang, J.-J. Chin. J. Org. Chem. 2006, 26, 1714 (in Chinese).

(纪建业, 李家柱, 王虎, 韩光范, 沈荣基, 王进军, 有机化学, 2006, 26, 1714.)

[11] Yin, J.-G.; Li, Y.-W.; Li, J.-Z.; Zhang, Q.; Pei, W.; Wang, J.-J. Chin. J. Org. Chem. 2011, 31, 1217 (in Chinese).

(殷军港, 李韵伟, 李家柱, 张千, 裴文, 王进军, 有机化学, 2011, 31, 1217.)

[12] (a) Houk, K. N.; Sins, J.; Duck, R. E. J. Am. Chem. Soc, 1973, 95, 7287.

(b) Houk, K. N.; Sins, J.; Watts, C. R. J. Am. Chem. Soc, 1973, 95, 7301.

[13] Wu, J.; Yin, J.-G.; Zhang, Q.; Sun, C.-M.; Li, F.-G.; Pei, W.; Wang, J.-J. Chin. J. Org. Chem. 2011, 31, 1653 (in Chinese).

(武进, 殷军港, 张千, 孙传民, 李付国, 裴文, 王进军, 有机化学, 2011, 31, 1653.)

[1]	Fakai Zou, Nengzhong Wang, Hui Yao, Hui Wang, Mingguo Liu, Nianyu Huang. Regio- and Stereo-selective Synthesis of 1β-/3R-Aryl Thiosugar [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 593-604.
[2]	Luyao Li, Zhongwen He, Zhenguo Zhang, Zhenhua Jia, Teck-Peng Loh. Application of Triaryl Carbenium in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 421-437.
[3]	Qinggang Mei, Qinghan Li. Recent Progress of Visible Light-Induced the Synthesis of C(3) (Hetero)arylthio Indole Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 398-408.
[4]	Penghui Li, Qingyang Xie, Fuxian Wan, Yuanhong Zhang, Lin Jiang. Synthesis and Fungicidal Activity of Novel Substituted Pyrimidine-5-carboxamides Bearing Cyclopropyl Moiety [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 650-656.
[5]	Weiqing Yang, Yanbing Ge, Yuanyuan Chen, Ping Liu, Haiyan Fu, Menglin Ma. Design and Synthesis of Fluorescent 1,8-Napthalimide Derivatives and Their Identification of Cysteine [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 180-194.
[6]	Shihang Yu, Jiawei Liu, Biyu An, Qinghua Bian, Min Wang, Jiangchun Zhong. Asymmetric Synthesis of the Contact Sex Pheromone of Neoclytus acuminatus acuminatus (Fabricius) [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 301-308.
[7]	Qianfan Zhao, Yongzheng Chen, Shiming Zhang. Application and Mechanism Study of Carbon-Based Metal-Free Catalysts in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 137-147.
[8]	Shan Chen, Zhilin Chen, Qiong Hu, Yanshuang Meng, Yue Huang, Pingfang Tao, Liru Lu, Guobao Huang. Recognition of Bis-thiourea Tweezers to Neutral Molecules in Non-Polar Solvent [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 277-281.
[9]	Huakun Wang, Xiaolong Ren, Yining Xuan. Study of the Halide Salt Catalyzed [3＋2] Cycloaddition of α,β-Epoxy Carboxylate with Isocyanate [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 251-258.
[10]	Yukun Jin, Baoyi Ren, Fushun Liang. Visible Light-Mediated Selective C—F Bond Cleavage of Trifluoromethyl Groups and Its Application in Synthesizing gem-Difluoro-Containing Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 85-110.
[11]	Cuiyun Ma, Hailan Luo, Fuhua Zhang, Dan Guo, Shuxing Chen, Fei Wang. Green Biosynthesis, Photophysical Properties and Application of 3-Pyrrolyl BODIPY [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 216-223.
[12]	Bozhen Wang, Jie Zhang, Chunhui Nian, Mingming Jin, Miaomiao Kong, Wulan Li, Wenfei He, Jianzhang Wu. Synthesis and Antitumor Activity of 3,4-Dichlorophenyl Amides [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 232-241.
[13]	Huanqing Li, Zhaohua Chen, Zujia Chen, Qiwen Qiu, Youcai Zhang, Sihong Chen, Zhaoyang Wang. Research Progress in Mercury Ion Fluorescence Probes Based on Organic Small Molecules [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3067-3077.
[14]	Ran Zhou, Chunmei Yuan, Tao Zhang, Piao Mao, Yi Liu, Kaini Meng, Hui Xin, Wei Xue. Design, Synthesis and Bioactivity of Chalcone Derivative Containing Quinazolinone [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3196-3209.
[15]	Ruixia Cao, Yuping Jia. Synthesis and Biological Activity of Novel Pyrrolo[2,3-d]pyrimidine Derivatives Containing Coumarin [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3304-3311.

具有氮杂环并叶绿素色基结构的二氢卟吩衍生物的合成

Synthesis of Chlorins with Chlorophyllous Chromophore Fused with Nitrogenous Heterocycle

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments