The aminolysis of purpurin-18 with aliphatic amines or aromatic amines was carried out by reflux and microwave assisted methods to obtain mono-amidated, di-amidated and carbonyl-imidizated products. The chemical modifications of purpurin-18 imides along their N21-NM23 axis produced the mixtures of purpurin-18 imides possessing atropisomeric and anomeric characteritics. The structures of new chlorophyll derivatives were characterized by UV, IR, 1H NMR, MS techniques and elemental analysis. The possible mechanisms about aminization reactions were tentatively proposed.
WANG Peng
,
YANG Ze
,
LI Jia-Zhu
,
YAO Nan-Nan
,
WANG Jin-Jun
. Aminolysis Reaction of Purpurin-18 and Synthesis of Chlorin Derivatives Related to Chlorophyll[J]. Chinese Journal of Organic Chemistry, 2012
, 32(02)
: 368
-375
.
DOI: 10.6023/cjoc1107031
[1] (a) Bellnier, D. A.; Greco, W. R.; Loewen, G. M.; Nava, H.; Oseroff, A. R.; Pandey, R. K.; Tsuchida, T.; Dougherty, T. J. Cancer Res. 2003, 63, 1806. (b) Steruberg, E. D.; Dolphin, D. Tetrahedron 1998, 54, 4151.
[2] Wang, J.-J. Chin. J. Org. Chem. 2005, 25, 1353 (in Chinese). (王进军, 有机化学, 2005, 25, 1353.)
[3] Pavlov, V. Y.; Ponomarev, G. V. Chem. Heterocycl. Compd. 2004, 40, 393.
[4] 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.)
[5] Ji, J.-Y.; Li, J.-Z.; Wang, H.; Li, F.-G.; Hang, G.-F.; Shen, R.-J.; Wang, J.-J. Chin. J. Org. Chem. 2006, 26, 1714 (in Chinese). (纪建业, 李家柱, 王虎, 李付国, 韩光范, 沈荣基, 王进军, 有 机化学, 2006, 26, 1714.)
[6] 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.)
[7] Wang, J.-J.; Zhao, L.-L.; Li, J.-J. Chin. J. Org. Chem. 2009, 29, 1598 (in Chinese). (王进军, 赵丽丽, 李家柱, 有机化学, 2009, 29, 1598.)
[8] Wang, J.-J.; Li, J. Z.; Li, Y.-W.; Jakus, J.; Shim, Y.-K. J. Porphyrins Phthalocyanines 2010, 14, 859.
[9] Li, J.-Z. M.S. Thesis, Yantai University, Yantai, 2007 (in Chinese). (李家柱, 硕士论文, 烟台大学, 烟台, 2007.)
[10] Han, G.-F.; Wang, J.-J.; Xu, Y.; Shim, Y.-K. Chin. J. Org. Chem. 2006, 26, 43 (in Chinese). (韩光范, 王进军, 瞿燕, 沈荣基, 有机化学, 2006, 26, 43.)