Chinese Journal of Organic Chemistry >
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).
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.
Yang Ze , Wang Zhen , Xu Xisen , Liu Yang , Qi Caixia , Wang Jinjun . Synthesis of Chlorins with Chlorophyllous Chromophore Fused with Nitrogenous Heterocycle[J]. Chinese Journal of Organic Chemistry, 2012 , 32(11) : 2099 -2107 . DOI: 10.6023/cjoc201206021
[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.)
/
| 〈 |
|
〉 |
