以缺电子炔烃为原料经1,3-偶极环加成反应合成3-芳基中氮茚的新方法
收稿日期: 2014-01-03
修回日期: 2014-01-26
网络出版日期: 2014-02-12
基金资助
国家自然科学基金（No.21202058）、江苏省自然科学基金（No.BK2011408）、江苏省高校重大（No. 13KJA150001）资助项目.
New Method for Synthesis of 3-Arylindolizines from Electron-Deficient Alkynes through 1, 3-Dipolar Cycloaddition
Received date: 2014-01-03
Revised date: 2014-01-26
Online published: 2014-02-12
Supported by
Project supported by the National Natural Science Foundation of China (No. 21202058), the Natural Science Foundation of Jiangsu Province (No. BK2011408), and the Department of Education of Jiangsu Province (No. 13KJA150001).
李国栋 , 胡华友 , 阚玉和 , 马奎蓉 . 以缺电子炔烃为原料经1,3-偶极环加成反应合成3-芳基中氮茚的新方法[J]. 有机化学, 2014 , 34(5) : 903 -908 . DOI: 10.6023/cjoc201401001
A novel and efficient procedure for the preparation of 3-aryl-indolizine by 1,3-dipolar cycloaddition was established. The pyridinium salts were prepared from the corresponding pyridines and benzyl halides. In the presence of cesium carbonate, electron-deficient alkynes reacted with the pyridinium salts in 1,4-dioxane through 1,3-dipolar cycloaddition followed by an aromatization reaction to generate the corresponding 3-aryl-indolizines. This method features cheap reagents, a simple workup procedure, mild conditions, high regioselectivity and generating the desired products in moderate to high yield (34%～81%).
Key words： indolizine; 1,3-dipolar cycloaddition; electron-deficient alkyne
[1] (a) Wang B.; Zhang C.-F. Chin. Wild Plant Resources 2009, 28, 6 (in Chinese).
(王冰, 张朝凤, 中国野生植物资源, 2009, 28, 6.)
(b) Ewing, J.; Hughes, G. K.; Ritchie, E. W.; Taylor, C. Nature 1952, 169, 618.
(c) Flitsch, W. In Comprehensive Heterocyclic Chemistry, Vol. 4, Eds.: Katritzki, A. R.; Rees, C. W., Pergamon, Oxford, 1984.
(d) Swinbourne, F. T.; Hunt, J.; Klinkert, K. In Advances in Heterocyclic Chemistry, Vol. 23, Eds.: Katritzki, A. R.; Boulton, A. J., Academic Press, New York, 1978.
(e) Michael, J. P. Nat. Prod. Rep. 2007, 24, 191.
[2] Hagishita, S.; Yamada, M.; Shirahase, K.; Okada, T.; Murakami, Y.; Ito, Y.; Matsuura, T.; Wada, M.; Kato, T.; Ueno, M.; Chikazawa, Y.; Yamada, K.; Ono, T.; Teshirogi, I.; Ohtani, M. J. Med. Chem. 1996, 39, 3636.
[3] Liao, Z.-Y.; Zhang, W.-N.; You, L.; Guo, W.; Zhang, J.; Sheng, C.-Q.; Yao, J.-Z.; Shan, X.-Y.; Wang, W.-Y. Chin. J. Med. Chem. 2008, 18, 105 (in Chinese).
(缪震元, 张万年, 游亮, 郭巍, 张晶, 盛春泉, 姚建忠, 车晓颖, 王文雅, 中国药物化学杂志, 2008, 18, 105.)
[4] Medda, S.; Jaisankar, P.; Manna, R. K.; Pal, B.; Giri, V. S.; Basu, M. K. J. Drug Targeting 2003, 11, 123.
[5] Gundersen, L.-L.; Negussie, A. H.; Ostbly, O. B. Arch. Pharm. 2003, 336, 191.
[6] Badorc, A.; Bono, F.; Bordes, M.; Guillo, N.; Herbert, J. M. US 2005203126, 2005 [Chem. Abstr. 2003, 139, p307679f].
[7] (a) Poissonnet, G.; Theret-Bettiol, M.-H.; Dodd, R. H. J. Org. Chem. 1996, 61, 2273.
(b) Smith, S. C.; Clarke, E. D.; Ridley, S. M.; Bartlett, D.; Greenhow, D. T.; Glithro, H.; Klong, A. Y.; Mitchell G. Mullier, G.. W. Pest Manage. Sci. 2005, 61, 16.
(c) Shen, Y.; Lv, P.; Chen, W.; Liu, P.; Zhang, M.; Zhu, H. Eur. J. Med. Chem. 2010, 45, 3184.
(d) Sonnenschein, H.; Henrich, G.; Resch-Genger, U.; Schulz, B. Dyes Pigm. 2000, 46, 23.
[8] Shen, Y.-M.; Wang, B.-X.; Feng, Y.-Y.; Shen, Z.-Y.; Shen, J.; Li, C.; Hu, H.-W. Chem. J. Chin. Univ. 2006, 27, 651 (in Chinese).
(沈永淼, 王炳祥, 冯玉英, 沈珠英, 沈健, 李邨, 胡宏纹, 高等学校化学学报, 2006, 27, 651.)
[9] Gundersen, L.-L.; Charnock, C.; Negussie, A. H.; Rise, F.; Teklu, S. Eur. J. Pharm. Sci. 2007, 30, 26.
[10] (a) Yue, G.-Z.; Huang, Q.-M.; Ziu, P. Chin. J. Org. Chem. 2007, 27, 1060 (in Chinese).
(乐贵洲, 黄乾明, 邹平, 有机化学, 2007, 27, 1060.)
(b) Yang, Y.-Z.; Chen, L.; Zhang, Z.-G.; Zhang, Y.-H. Org. Lett. 2011, 13, 1342.
(c) Xia, J.-B.; You, S.-L. Org. Lett. 2009, 11, 1187.
(d) Huang, L.-H.; Niu, T.-M.; Wu, J.; Zhang, Y.-H. J. Org. Chem. 2011, 76, 1759.
[11] (a) Boekelheide, V.; Fahrenholtz, K. J. Am. Chem. Soc. 1961, 83, 458.
(b) Tsuge, O.; Kanemasa, S.; Takenaka, S. Bull. Chem. Soc. Jpn. 1985, 58, 3320.
(c) Li, B.; Pan, G.-J.; He, T.; Hu, H.-W. Chem. J. Chin. Univ. 2004 25, 1461 (in Chinese).
(李斌, 潘国骏, 何婷, 胡宏纹, 高等学校化学学报, 2004, 25, 1461.)
(d) Wang, B.-X.; Xu, Z.-X.; Wu, J. Chin. J. Org. Chem. 2006, 26, 1587 (in Chinese).
(王炳祥, 徐助雄, 吴婧, 有机化学, 2006, 26, 1587.)
[12] (a) Hu, H.-Y.; Shi, K.-B.; Hou, R.-R.; Zhang, Z.-C.; Zhu, Y.-L.; Zhou, J.-F. Synthesis 2010, 4007.
(b) Chuprakov, S.; Hwang, F. W.; Gevorgyan, V. Angew. Chem., Int. Ed. 2007, 46, 4757.
(c) Li, Y.; Zhou, Z.; Ye, W.; Liu, J.; Yao, J.; Wang, C. J. Chem. Res. 2013, 526.
[13] Anastasia, L.; Negishi, E. Org. Lett. 2001, 3, 3111.
[14] Alonso, D. A.; Nájera, C.; Pacheco, M. C. J. Org. Chem. 2004, 69, 1615.
[15] Palimkar, S. S.; Kumar, P. H.; Jogdand, N. R.; Daniel, T.; Lahoti, R. J.; Srinivasan, K. V. Tetrahedron Lett. 2006, 47, 5527.
[16] Liu, B.; Qin, X.-R.; Li, K.-Z.; Li, X.-Y.; Guo, Q.; Lan, J.-B.; You, J.-S. Chem.-Eur. J. 2010, 16, 11836.
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