SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2012 >Issue 03: 632 - 638

DOI: https://doi.org/10.6023/cjoc1108192

Notes

Modification for the E-Ring of 132-Oxo-pyropheophorbide-a and Synthesis of Chlorin Derivatives

  • Wu Xuran ,
  • Liu Chao ,
  • Yang Ze ,
  • Yao Nannan ,
  • Wang Jinjun
Expand
  • College of Chemistry and Chemical Engineering, Yantai University, Yantai 264005

Received date: 2011-08-19

  Revised date: 2011-10-18

  Online published: 2012-03-24

Supported by

Project supported by the National Natural Science Foundation of China (No. 20972036), the Natural Science Foundation of Shangdong Province of China (No. Y2008B49), and the International Science and Technology Project between Governments of China and Hungary (No. 2008-333-4-32).

Fold

Abstract

The methyl 132-oxo-pyropheophorbide-a was used as a starting material and converted quantitatively into purpourin- 18 by allomerization and rearrangement in the basic condition. Under the catalysis of BF3, the aldol reaction of acetophenone gave 131-phenylacylmethylene-substituted chlorin and keto-rhodin, respectively. The Knoevenagel reaction with malononitrile, condensation with aminothiocarbamide, rearrangement with diazomethane and Grignard reaction with benzyl megnesium bromide afforded a series of chlorins possessing long wavelength absorption. The structures of all the new chlorins with basic skeleton of chlorophyll were characterized by UV, IR, 1H NMR spectra and elemental analysis.

Key words： chlorophyll; methyl 132-oxo-pyropheophorbide-a; chlorin; chemical modification; synthesis

Cite this article

Wu Xuran , Liu Chao , Yang Ze , Yao Nannan , Wang Jinjun . Modification for the E-Ring of 132-Oxo-pyropheophorbide-a and Synthesis of Chlorin Derivatives[J]. Chinese Journal of Organic Chemistry, 2012 , (03) : 632 -638 . DOI: 10.6023/cjoc1108192

References

[1] Pavlov, V. Y.; Ponomarev, G. V. Chem. Heterocycl. Compd. 2004,40, 393.  

[2] Morishita, H.; Tamiaki, H. Bioorg. Med. Chem. 2003, 11, 4049.  

[3] (a) Wang, J.-J. Chin. J. Org. Chem. 2005, 25, 1353 ( in Chinese).(王进军, 有机化学, 2005, 25, 1353.)(b) Wang, J.-J.; Li, F.-G.; Li, Y.-W. Chin. J. Org. Chem. 2011, 31,68 (in Chinese).(王进军, 李付国, 李韵伟, 有机化学, 2011, 31, 68.)(c) Yin, J.-G.; Li, Y.-W; Li, J.-Z.; Zhang, Q.; Pei, W.; Wang, J.-J.Chin. J. Org. Chem. 2011, 31, 1213 ( in Chinese).(殷军港, 李韵伟, 李家柱, 张千, 裴文, 王进军, 有机化学,2011, 31, 1213.)

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

[5] Kozyrev, A. N.; Alderfer, J. L.; Dougherty, T. J.; Pandey, R. K.Chem. Commun, 1998 1083

[6] Li, J.-J.; Liu, W.-H.; Li, F.-G.; Wang, J.-J.; Suo, Y.-R.; Liu, Y.-J.Chin. J. Org. Chem. 2007, 27, 1594 (in Chinese).(李家柱, 刘万卉, 李付国, 王进军, 索有瑞, 刘永军, 有机化学,2007, 27, 1594.)

[7] (a) Wang, J.-J.; Li, J-Z.; Wu, X.-R.; Shim, Y.-K. Chin. J. Chem.2006, 24, 933.(b) Wang, J.-J.; Zhang, P.; Wang, P.; Chen, G.-L.; Li, F.-G. Chin. J. Org. Chem. 2010, 30, 1192 ( in Chinese).(王进军, 张朋, 王朋, 陈冠龙, 李付国, 有机化学, 2010, 30,1192.)(c) Wang, J.-J.; Li, J.-Z.; Li, Y.-W.; Jakus. J.; Shim, Y.-K. J. PorphyrinsPhthalocyanines 2010, 14, 859

[8] Wang, J.-J.; Ji, J.-Y.; Han, G.-F; Shen, R.-K.; Mori, A.; Hatsui T.Chin. J. Org. Chem. 2004, 24, 53 ( in Chinese).(王进军, 纪建业, 韩光范, 沈荣基, 森章, 初井敏一, 有机化学,2004, 24, 53.)

[9] Zheng. G.; Potter, W. R.; Camacho, S. H.; Misser, J. R.; Wang, G.S.; Bellnier, D. A.; Henderson, B. W.; Rodgers, M. A. J.; Dougherty,T. G.; Pandey, R. K. J. Med. Chem. 2001, 44, 1540.  

[10] Goswami, L. N.; Ethirajan, M.; Dobhal, M. P.; Zhang, M.; Missert,J. R.; Shibata, M.; Kadish, K. M. K.; Pandey, K. R. J. Org. Chem.2009, 74(2), 568.  

[11] Wang, P. M.S. Thesis, Yantai University, Yantai, 2007 (in Chinese).(王朋, 硕士论文, 烟台大学, 烟台, 2009.)

[12] Tamiaki, H.; Kitamodo, H.; Nishikawa, A.; Hibino, T.; Shibata, R.Bioorg. Med. Chem. 2004, 12, 1657.  
Options
Outlines

/

〈 〉