脱镁叶绿酸-a 甲酯与邻苯二胺发生缩合和重排反应, 分别给出(2,3-n)-苯并咪唑并红紫素-18 甲酯、(2,3-o)-苯并咪唑并红紫素-18 甲酯、(2,3-n)-喹喔啉并焦脱镁叶绿酸甲酯和二氢卟吩-p6 三甲酯. 针对苯并咪唑并红紫素-18 的20-meso-位和12-位甲基进行氟代、氯代、溴代、碘代和空气氧化反应, 完成了一系列具有叶绿素基本碳架的苯并咪唑并二氢卟吩类衍生物的合成. 所得新的叶绿素衍生物的化学结构均经UV, IR, 1H NMR, 质谱及元素分析予以证实.
刘冉冉
,
王鲁敏
,
殷军港
,
武进
,
刘超
,
张朋
,
王进军
. 具有叶绿素基本碳架的苯并咪唑并红紫素-18 衍生物的合成[J]. 有机化学, 2012
, 32(02)
: 318
-325
.
DOI: 10.6023/cjoc1107064
The condensation and rearrangement reactions of methyl pheophorbide-a with 1,2-benzenediamine afforded benzimidazolo[ 2,1-n]purpurin-18 methyl ester, benzimidazolo[1,2-o]purpurin-18 methyl ester, quinoxalino[2,3-n]-deoxopyropheophorbide- a methyl ester and chlorine-p6 trimethyl ester. The syntheses of benzimidazol-fused chlorins with the basic skeleton of chlorophyll were carried out by fluorination, chlorination, bromination and iodonation for 20-meso-position and allomerization for methyl group at 12-position. The structures of new chlorophyll derivatives were characterized by UV, IR, 1H NMR, MS spectra and elemental analysis.
[1] Vaughanr, K. R.; Weishaupt, K. R.; Dougherty, T. J. J. Photochem. Photobiol. 1999, 70, 781.
[2] Zhan, P.-Y.; Li, D.-F.; Wang, J.-J. Chin. J. Org. Chem. 2008, 28, 2039 (in Chinese ). (战佩英, 李东风, 王进军, 有机化学, 2008, 28, 2039.)
[3] Pavlov, V. Y.; Ponomarev, G. V. Chem. Heterocycl. Compd. 2004, 40, 393.
[4] Lalit, N.; Ethirajan, G. M.; Dobhal, M. P.; Zhang, M.; Missert, J. R.; Shibata, M.; Kadish, K. M.; Pandey, R. K. J. Org. Chem. 2009, 74, 568.
[5] Wang, J.-J. Chin. J. Org. Chem. 2005, 25, 1353 (in Chinese). (王进军, 有机化学, 2005, 25, 1353.)
[6] Kozyrev, A. N.; Suresh, V.; Das, S.; Senge, M. O.; Shibata, M.; Dougherty, T. J.; Pandey, R. K. Tetrahedron 2000, 56, 3353.
[7] (a) Steruberg, E. D.; Dolphin, D. Tetrahedron 1998, 54, 4151. (b) Smith, K. M.; Gogg, D. A.; Simpson, D. J. J. Am. Chem. Soc. 1985, 107, 4946.
[8] 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.)
[9] Wang, J.-J.; Ji, J.-Y.; Han, G.-F.; Wu, X.-R.; Wang, L.-M.; Shen, R.-J. Acta Chim. Sinica 2003, 61, 907 (in Chinese). (王进军, 纪建业, 韩光范, 邬旭然, 王鲁敏, 沈荣基, 化学学报, 2003, 62, 302.)
[10] Schenk, J.; Daessler, H. G. Pharmazie 1969, 24, 419
[11] Li, Y.-W. M.S. Thesis, Yantai University, Yantai, 2008 (in Chinese). (李韵伟, 硕士论文, 烟台大学, 烟台, 2008.)
[12] Wang, P. M.S. Thesis, Yantai University, Yantai, 2008 (in Chinese). (王朋, 硕士论文, 烟台大学, 烟台, 2009.)
