Citation: Yan Yizhe, Li Zheng, Cui Chang, Liu Yanqi. Synthesis of 2, 3, 5, 6-Tetrasubstituted Pyridines via Copper-Catalyzed Domino Oxidative Annulation of 1, 3-Dicarbonyl Compounds with Methanol and Ammonium Acetate[J]. Chinese Journal of Organic Chemistry, ;2018, 38(12): 3381-3385. doi: 10.6023/cjoc201807003 shu

Synthesis of 2, 3, 5, 6-Tetrasubstituted Pyridines via Copper-Catalyzed Domino Oxidative Annulation of 1, 3-Dicarbonyl Compounds with Methanol and Ammonium Acetate

Yan Yizhe ^a,b,, ,
Li Zheng ^a ,
Cui Chang ^a ,
Liu Yanqi ^a,,

a.
School of Food and Biological Engineering, Zhengzhou University of Light Industry, Zhengzhou 450000
b.
Collaborative Innovation Center of Food Production and Safety, Henan 450000

Corresponding author: Yan Yizhe, yanyizhe@mail.ustc.edu.cn Liu Yanqi, liuyanqi@zzuli.edu.cn
Received Date: 1 July 2018
Revised Date: 12 July 2018
Available Online: 22 December 2018
Fund Project: the Grants Program of Youth Backbone Teachers Training Object of Zhengzhou University of Light Industry the Scientific and Technological Breakthrough Plan of Henan Province 182102310903Project supported by the National Natural Science Foundation of China (No. 21502177), the Scientific and Technological Breakthrough Plan of Henan Province (No. 182102310903), the Doctoral Research Foundation of Zhengzhou University of Light Industry (No. 2014BSJJ032), and the Grants Program of Youth Backbone Teachers Training Object of Zhengzhou University of Light Industrythe Doctoral Research Foundation of Zhengzhou University of Light Industry 2014BSJJ032the National Natural Science Foundation of China 21502177

Figures(4)

A copper-catalyzed oxidative formal cycloaddition of 1, 3-dicarbonyl compounds, methanol and ammonium acetate was first demonstrated, affording symmetrical 2, 3, 5, 6-tetrasubstituted pyridines in moderate to excellent yields. Methanol was employed as the carbon synthon as well as the reaction solvent. The preliminary mechanistic studies revealed that the reaction underwent a radical pathway and the C(sp³)-H bond cleavage of methanol was the rate-determining step. This method is operationally simple and environmentally friendly.
- copper,
- oxidative annulation,
- pyridine,
- methanol
1. [1]
  (a) Roughley, S. D.; Jordan, A. M. J. Med. Chem. 2011, 54, 3451.
  (b) Carey, J. S.; Laffan, D.; Thomson, C.; Williams, M. T. Org. Biomol. Chem. 2006, 4, 2337.
  (c) Michael, J. P. Nat. Prod. Rep. 2005, 22, 627.
2. [2]
  Henry, G. D. Tetrahedron 2004, 60, 6043. doi: 10.1016/j.tet.2004.04.043
3. [3]
  (a) Xia, J.-J.; Wang, G.-W. Synthesis 2005, 2379.
  (b) Litvic, M.; Cepanec, L.; Filipan, M.; Kos, K.; Bartolincic, A.; Druskovic, V.; Tibi, M. M.; Vinkovic, V. Heterocycles 2005, 65, 23.
  (c) Nasr-Esfahani, M.; Karami, B.; Behzadi, M. J. Heterocycl. Chem. 2009, 46, 931.
  (d) Xia, J.; Zhang, K.; Ju, J. Chin. J. Org. Chem. 2009, 29, 1849 (in Chinese).
  (夏静静, 张克华, 鞠俊, 有机化学, 2009, 29, 1849).
  (e) Chen, S.; Hossain, M. S.; Foss, F. W. ACS Sustainable Chem. Eng. 2013, 1, 1045.
  (f) Abdel-Mohsen, H. T.; Conrad, J.; Beifuss, U. Green Chem. 2012, 14, 2686.
4. [4]
  Chang, L.; Lai, J.; Yuan, G. Chin. J. Chem. 2016, 34, 887. doi: 10.1002/cjoc.201600255
5. [5]
  Yan, Y.; Li, H.; Li, Z.; Niu, B.; Shi, M.; Liu, Y. J. Org. Chem. 2017, 82, 8628. doi: 10.1021/acs.joc.7b01516
6. [6]
  (a) Guo, S.-R.; Kumar, P. S.; Yang, M. Adv. Synth. Catal. 2017, 359, 2.
  (b) Lakshman, M. K.; Vuram, P. K. Chem. Sci. 2017, 8, 5845.
7. [7]
  (a) Tang, L.; Guo, X.; Yang, Y.; Zha, Z.; Wang, Z. Chem. Commun. 2014, 50, 6145.
  (b) Zhang, W; Guo, F.; Wang, F.; Zhao, N.; Liu, L.; Li, J.; Wang, Z. Org. Biomol. Chem. 2014, 12, 5752.
  (c) Tang, L.; Yang, Y.; Wen, L.; Zhang, S.; Zha, Z.; Wang, Z. Org. Chem. Front. 2015, 2, 114.
  (d) You, Q.; Wang, F.; Wu, C.; Shi, T.; Min, D.; Chen, H.; Zhang, W. Org. Biomol. Chem. 2015, 13, 6723.
  (e) Tiwari, A. R.; T. A.; Bhanage, B. M. Org. Biomol. Chem. 2015, 13, 10973.
  (f) Li, J.; Zhang, J.; Yang, H.; Gao, Z.; Jiang, G. J. Org. Chem. 2017, 82, 765.
  (g) Guan, Q.; Sun, Q.; Wen, L.; Zha, Z.; Yang, Y.; Wang, Z. Org. Biomol. Chem. 2018, 16, 2088.
8. [8]
  (a) Yan, Y.; Zhang, Y.; Feng, C.; Zha, Z.; Wang, Z. Angew. Chem., Int. Ed. 2012, 51, 8077.
  (b) Yan, Y.; Li, Z.; Li, H.; Cui, C.; Shi, M.; Liu, Y. Org. Lett. 2017, 19, 6228.
9. [9]
  (a) Zhang, L.; Fan, F.; Yang, J.; Liu, Z. Org. Lett. 2014, 16, 3396.
  (b) Xu, Z.; Hang, Z.; Chai, L.; Liu, Z. Org. Lett. 2016, 18, 4662.
10. [10]
  (a) Miyamura, H.; Maehata, K.; Kobayashi, S. Chem. Commun. 2010, 46, 8052.
  (b) Bai, C.-B.; Wang, N.-X.; Wang, Y.-J.; Lan, X.-W.; Xing, Y.; Wen, J.-L. RSC Adv. 2015, 5, 100531.
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