Citation: Zhao Yuying, Wang Erbing, Wang Yingli. Iodine-Promoted Three-Component Reaction of β-Keto Esters, Chalcones and Ammonium Acetate for the Synthesis of Poly-substituted Pyridines[J]. Chinese Journal of Organic Chemistry, ;2017, 37(4): 866-872. doi: 10.6023/cjoc201701006 shu

Iodine-Promoted Three-Component Reaction of β-Keto Esters, Chalcones and Ammonium Acetate for the Synthesis of Poly-substituted Pyridines

a.
Institute of Chemical and Biological Technology, Taiyuan University of Science and Technology, Taiyuan 030021
b.
Department of Traditional Chinese Pharmacology, Shanxi University of Traditional Chinese Medicine, Taiyuan 030024

Corresponding author: Zhao Yuying, zhaoyuyingtyust@163.com
Received Date: 5 January 2017
Revised Date: 5 March 2017

Fund Project: the Science and Technology Key Project of Shanxi Province 20130313015-2

Figures(3)

A three-component reaction for the synthesis of poly-substituted pyridines from β-keto esters, chalcones and ammonium acetate promoted by iodine has been reported. Advantages of the present method include ready availability of starting materials, broad scope of substrates, and convenience of operation.
- molecular iodine,
- muti-component reaction,
- pyridine
1. [1]
  (a) McGrath, N. A.; Brichacek, M.; Njardarson, J. T. J. Chem. Educ. 2010, 87, 1348.
  (b) Tang, B.; Yu, F.; Li, P.; Tong, L.; Duan, X.; Xie, T.; Wang, X. J. Am. Chem. Soc. 2009, 131, 3016.
  (c) Yoo, K. S.; Park, C. P.; Yoon, C. H.; Sakaguchi, S.; O'Neil l, J.; Jung, K. W. Org. Lett. 2007, 9, 3933.
2. [2]
  For selected reviews on the synthesis of pyridines, see: (a) Allais, C.; Grassot, J.-M.; Rodriguez, J.; Constantieux, T. Chem. Rev. 2014, 114, 10829.
  (b) Hill, M. D. Chem. Eur. J. 2010, 16, 12052.
  (c) Henry, G. D. Tetrahedron 2004, 60, 6043. For selected examples on the synthesis of pyridines, see:
  (d) Zhang, X.; Ying, W.; Wu, W.; Li, J.; Hua, J. Acta Chim. Sinica 2015, 73, 272 (in Chinese). (张晓瑜, 应伟江, 武文俊, 李晶, 花建丽, 化学学报, 2015, 73, 272.)
  (e) Shao, T.; Jiang, Z. Acta Chim. Sinica 2017, 75, 70 (in Chinese). (邵天举, 江智勇, 化学学报, 2017, 75, 70.)
  (f) Chang, L.; Lai, J.; Yuan, G. Chin. J. Chem. 2016, 34, 887. (g) Yang, F.; Sun, J.; Yan, C. Chin. J. Chem. 2015, 33, 1371.
3. [3]
  Stout, D. M.; Meyers, A. I. Chem. Rev. 1982, 82, 223. doi: 10.1021/cr00048a004
4. [4]
  Chichibabin, A. E.; Zeide, O. A. J. Russ. Phys.-Chem. Soc. 1906, 37, 1229.
5. [5]
  (a) Zecher, W.; Kröhnke, F. Chem. Ber. 1961, 94, 690.
  (b) Zecher, W.; Kröhnke, F. Chem. Ber. 1961, 94, 698.
6. [6]
  (a) Liéby-Muller, F.; Allais, C.; Constantieux, T.; Rodriguez, J. Chem. Commun. 2008, 4207.
  (b) Allais, C.; Constantieux, T.; Rodriguez, J. Chem. Eur. J. 2009, 15, 12945.
  (c) Allais, C.; Liéby-Muller, F.; Rodriguez, J.; Constantieux, T. Eur. J. Org. Chem. 2013, 4131.
  (d) Allais, C.; Liéby-Muller, F.; Constantieux, T.; Rodriguez, J. Adv. Synth. Catal. 2012, 354, 2537.
7. [7]
  Song, Z.; Huang, X.; Yi, W.; Zhang, W. Org. Lett. 2016, 18, 5640. doi: 10.1021/acs.orglett.6b02883
8. [8]
  For selected examples on the reaction catalyzed or promoted by iodine, see: (a) Ren, X.; Wang, G.; Tang, X.; Zhao, W. Chin. J. Org. Chem. 2015, 35, 1733 (in Chinese). (任相伟, 王光伟, 唐向阳, 赵温涛, 有机化学, 2015, 35, 1733.)
  (b) Wang, D.; Zhang, R.; Lin, S.; Deng, R.; Yan, Z. Chin. J. Org. Chem. 2016, 36, 2757 (in Chinese). (王丁意, 张荣兴, 林森, 邓瑞红, 严兆华, 有机化学, 2016, 36, 2757.)
  (c) Meng, T.; Chen, R.; Liu, L.; Wang, T.; Liu, X.; Zhao, W. Chin. J. Org. Chem. 2015, 35, 2108 (in Chinese). (孟团结, 陈荣祥, 刘澜涛, 王涛, 刘新明, 赵文献, 有机化学, 2015, 35, 2108.) For selected reviews on iodine, see:
  (d) Liu, D.; Lei, A. Chem. Asian J. 2015, 10, 806.
  (e) Zhao, J.; Gao, W.; Chang, H.; Li, X.; Liu, Q.; Wei, W. Chin. J. Org. Chem. 2014, 34, 1941 (in Chinese). (赵巾巾, 高文超, 常宏宏, 李兴, 刘强, 魏文珑, 有机化学, 2014, 34, 1941.)
  (f) Wu, X.; Gong, J.; Qi, X. Org. Biomol. Chem. 2014, 12, 5807.
  (g) Shen, S.; Xu, X.; Ji, S. Chin. J. Org. Chem. 2009, 29, 806 (in Chinese). (沈舒苏, 徐小平, 纪顺俊, 有机化学, 2009, 29, 806.)
9. [9]
  (a) Gao, W.-C.; Hu, F.; Huo, Y.-M.; Chang, H.-H.; Li, X.; Wei, W.-L. Org. Lett. 2015, 17, 3914.
  (b) Gao, Q.; Liu, S.; Wu, X.; Zhang, J.; Wu, A. Org. Lett. 2015, 17, 2960.
  (c) Yan, Y.; Xu, Y.; Niu, B.; Xie, H.; Liu, Y. J. Org. Chem. 2015, 80, 5581.
  (d) Gao, Q.; Liu, S.; Wu, X.; Wu, A. Org. Lett. 2014, 16, 4582.
10. [10]
  Zhao, Y.; Wang, E.; Wang, Y. Chin. J. Org. Chem. 2016, 36, 1681 (in Chinese).
11. [11]
  For the synthesis of intermediate A, see: Stavber, G.; Iskra, J.; Zupan, M.; Stavber, S. Adv. Synth. Catal. 2008, 350, 2921. For the conversion from A to 3a, see Supporting Information.
12. [12]
  Zhang, Q.-R.; Huang, J.-R.; Zhang, W.; Dong, L. Org. Lett. 2014, 16, 1684. doi: 10.1021/ol500345n
13. [13]
  Xuan, Z.; Rathwell, K.; Lee, S. Asian J. Org. Chem. 2014, 3, 1108. doi: 10.1002/ajoc.v3.10
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