Citation: Chen Liang, Wang Baoqu, Zhao Yucheng, Yan Shengjiao, Lin Jun. One-Pot Synthesis of Multisubstituted Chromone-Fused Bicyclic Pyridine Compounds[J]. Chinese Journal of Organic Chemistry, ;2017, 37(6): 1433-1442. doi: 10.6023/cjoc201612038 shu

One-Pot Synthesis of Multisubstituted Chromone-Fused Bicyclic Pyridine Compounds

Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science andTechnology, Yunnan University, Kunming 650091

Corresponding author: Yan Shengjiao, yansj@ynu.edu.cn Lin Jun, linjun@ynu.edu.cn
Received Date: 12 December 2016
Revised Date: 21 January 2017

Fund Project: the National Natural Science Foundation of China U1202221the Talent Found in Yunnan Province 2012HB001the National Natural Science Foundation of China 21362042the National Natural Science Foundation of China 21662042the National Natural Science Foundation of China 21262042the Excellent Young Talents of Yunnan University XT412003

Figures(1)

A concise and environment friendly route for the synthesis of multisubstituted chromone-fused bicyclic pyridine compounds via one-step reaction of chromone-3-carboxaldehyde 1 and N-benzyl nitro ketene aminals (NBNKAs, 2) in ethanol media has been developed. The targeted compounds 3 can efficiently obtain by filter without extra post-treatment. The reaction is particularly attractive due to following features: low-cost and biocompatibility solvent, mild temperature, atom economy, high yields, and potential biological activity.
- environment friendly,
- atom economy,
- catalyst-free,
- bicyclic pyridine,
- neonicotinoids
1. [1]
  Hunt, A. J.; Sin, E. H. K.; Marriott, R.; Clark, J. H. CHemSusChem 2010, 3, 306. doi: 10.1002/cssc.200900169
2. [2]
  Agana, B. A.; Reeve, D.; Orbell, J. D. J Environ. Manage. 2013, 114, 445. doi: 10.1016/j.jenvman.2012.10.047
3. [3]
  Marr, P. C.; Marr, A. C. Green Chem. 2016, 18, 105. doi: 10.1039/C5GC02277K
4. [4]
  Marteel-Parrish, A. E. J. Chem. Educ. 2014, 91, 1084. doi: 10.1021/ed400393b
5. [5]
  Trost, B. M. Science 1991, 254, 1471. doi: 10.1126/science.1962206
6. [6]
  Misono, M. Yuki Gosei Kagaku Kyokaishi 2003, 61, 406. doi: 10.5059/yukigoseikyokaishi.61.406
7. [7]
  Hartman, G. J.; Jin, Q. Z.; Collins, G. J.; Lee, K. N.; Ho, C. T.; Chang, S. S. J. Agric. Food Chem. 1983, 31, 1030. doi: 10.1021/jf00119a027
8. [8]
  Ren, T.; Liu, W.; Xue, Q.; Wang, H. Lubr. Sci. 1993, 5, 205. doi: 10.1002/(ISSN)1557-6833
9. [9]
  Ueda, Y.; Connolly, T. P.; Kadow, J. F.; Meanwell, N. A.; Wang, T.; Chen, C.-P. H.; Yeung, K.-S.; Zhang, Z.; Leahy, D. K.; Pack, S. K.; Soundararajan, N.; Sirard, P.; Levesque, K.; Thoraval, D. US 20050209246, 2005[Chem. Abstr. 2005, 143, 306343].
10. [10]
  Garuti, L.; Roberti, M.; Pizzirani, D. Mini-Rev. Med. Chem. 2007, 7, 481. doi: 10.2174/138955707780619626
11. [11]
  Schultz, C.; Link, A.; Leost, M.; Zaharevitz, D. W.; Gussio, R.; Sausville, E. A.; Meijer, L.; Kunick, C. J. Med. Chem. 1999, 42, 2909. doi: 10.1021/jm9900570
12. [12]
  Pluta, K.; Morak-Mlodawska, B.; Jelen, M. Eur. J. Med. Chem. 2011, 46, 3179. doi: 10.1016/j.ejmech.2011.05.013
13. [13]
  Sujatha, K.; Shanmugam, P.; Perumal, P. T.; Muralidharan, D.; Rajendran, M. Bioorg. Med. Chem. Lett. 2006, 16, 4893. doi: 10.1016/j.bmcl.2006.06.059
14. [14]
  Helal, C. J.; Kang, Z.; Hou, X.; Pandit, J.; Chappie, T. A.; Humphrey, J. M.; Marr, E. S.; Fennell, K. F.; Chenard, L. K.; Fox, C.; Schmidt, C. J.; Williams, R. D.; Chapin, D. S.; Siuciak, J.; Lebel, L.; Menniti, F.; Cianfrogna, J.; Fonseca, K. R.; Nelson, F. R.; O'Connor, R.; MacDougall, M.; McDowell, L.; Liras, S. J. Med. Chem. 2011, 54, 4536. doi: 10.1021/jm2001508
15. [15]
  Kim, I. Y.; Kim, S. H. KR 2016006050, 2016[Chem. Abstr. 2016, 164, 225869].
16. [16]
  Lhassani, M.; Chavignon, O.; Chezal, J.-M.; Teulade, J.-C.; Chapat, J.-P.; Snoeck, R.; Andrei, G.; Balzarini, J.; De Clercq, E.; Gueiffier, A. Eur. J. Med. Chem. 1999, 34, 271. doi: 10.1016/S0223-5234(99)80061-0
17. [17]
  Alcarazo, M.; Roseblade, S. J.; Cowley, A. R.; Fernandez, R.; Brown, J. M.; Lassaletta, J. M. J. Am. Chem. Soc. 2005, 127, 3290. doi: 10.1021/ja0423769
18. [18]
  Mizushige, K.; Ueda, T.; Yukiiri, K.; Suzuki, H. Cardiovasc. Drug Rev. 2002, 20, 163.
19. [19]
  Ankley, G. T.; Kahl, M. D.; Jensen, K. M.; Hornung, M. W.; Korte, J. J.; Makynen, E. A.; Leino, R. L. Toxicol. Sci. 2002, 67, 121. doi: 10.1093/toxsci/67.1.121
20. [20]
  Veber, D. F.; Johnson, S. R.; Cheng, H.-Y.; Smith, B. R.; Ward, K. W.; Kopple, K. D. J. Med. Chem. 2002, 45, 2615. doi: 10.1021/jm020017n
21. [21]
  Bai, D.; Lummis, S. C. R.; Leicht, W.; Breer, H.; Sattelle, D. B. Pestic. Sci. 1991, 33, 197. doi: 10.1002/ps.v33:2
22. [22]
  Feng, X.-G.; Liu, X.-W.; Han, Z.-L.; Guan, L.-T.; Xu, L.-Z. J. Qingdao Univ. Sci. Technol., Nat. Sci. Ed. 2012, 33, 381.
23. [23]
  Li, J.; Huang, T.; Li, L.; Ding, T.; Zhu, H.; Yang, B.; Ye, Q.; Gan, J. J. Agric. Food Chem. 2016, 64, 8109. doi: 10.1021/acs.jafc.6b03422
24. [24]
  Tomizawa, M.; Casida, J. E. Annu. Rev. Pharmacol. Toxicol. 2005, 45, 247. doi: 10.1146/annurev.pharmtox.45.120403.095930
25. [25]
  Bao, H.; Shao, X.; Zhang, Y.; Deng, Y.; Xu, X.; Liu, Z.; Li, Z. J. Agric. Food Chem. 2016, 64, 5148. doi: 10.1021/acs.jafc.6b01512
26. [26]
  Lu, S.; Zhuang, Y.; Wu, N.; Feng, Y.; Cheng, J.; Li, Z.; Chen, J.; Yuan, J.; Xu, X. J. Agric. Food Chem. 2013, 61, 10858. doi: 10.1021/jf403272h
27. [27]
  Shao, X.; Xu, Z.; Zhao, X.; Xu, X.; Tao, L.; Li, Z.; Qian, X. J. Agric. Food Chem. 2010, 58, 2690. doi: 10.1021/jf902513t
28. [28]
  (a) Huang, Z.; Wang, M. Heterocycles 1994, 37, 1233.
  (b) Kong, L.; Yang, R.; Du, X.; Yan, S.; Lin, J. Chin. J. Org. Chem. 2016, 36, 2437 (in Chinese).
  (孔令斌, 杨瑞霞, 杜璇璇, 严胜骄, 林军, 有机化学, 2016, 36, 2437.)
  (c) Peng, M.; Yang, R.; Liu, X.; Yan, S.; Lin, J. Chin. J. Org. Chem. 2015, 35, 1754 (in Chinese).
  (彭美阳, 杨瑞霞, 刘昔敏, 严胜骄, 林军, 有机化学, 2015, 35, 1754.)
29. [29]
  (a) Chen, X.-B.; Liu, Z.-C.; Lin, X.-R.; Huang, R.; Yan, S.-J.; Lin, J. ACS Sustainable Chem. Eng. 2014, 2, 2391.
  (b) Luo, D.; Cui, S.; Hu, X.; Yan, S.; Lin, J. Chin. J. Org. Chem. 2017, 37, 166 (in Chinese).
  (罗大云, 崔时胜, 胡兴梅, 林军, 严胜骄, 有机化学, 2017, 37, 166.)
30. [30]
  Yu, F.-C.; Huang, R.; Ni, H.; Fan, J.; Yan, S.-J.; Lin, J. Green Chem. 2013, 15, 453. doi: 10.1039/C2GC36552A
31. [31]
  Chen, X.-B.; Liu, Z.-C.; Yang, L.-F.; Yan, S.-J.; Lin, J. ACS Sustainable Chem. Eng. 2014, 2, 1155. doi: 10.1021/sc500170d
32. [32]
  Xiao, X.; Wang, X.; Gui, X.; Chen, L.; Huang, B. Chem. Biodiversity 2016, 11, 1427.
33. [33]
  Mir, S. A. Int. J. PharmTech Res. 2016, 9, 70.
34. [34]
  (a) Ding, Z.-W.; Tan, Q.-T.; Liu, B.-X.; Xu, K.; Xu, B. Acta Chim. Sinica 2015, 73, 1302 (in Chinese).
  (丁正伟, 谭启涛, 刘秉新, 张可, 许斌, 化学学报, 2015, 73, 1302.)
  (b) Zhao, J.-B.; Zhang, Q. Acta Chim. Sinica 2015, 73, 1235 (in Chinese).
  (赵金钵, 张前, 化学学报, 2015, 73, 1235.)
35. [35]
  Alizadeh, A.; Bayat, F.; Zhu, Z. Res. Chem. Intermed. 2016, 42, 5927. doi: 10.1007/s11164-015-2414-6
36. [36]
  Yaqub, M.; Perveen, R.; Shafiq, Z.; Pervez, H.; Tahir, M. N. Synlett 2012, 23, 1755. doi: 10.1055/s-00000083
37. [37]
  Nishiwaki, H.; Nakagawa, Y.; Takeda, D. Y.; Okazawa, A.; Akamatsu, M.; Miyagawa, H.; Ueno, T.; Nishimura, K. Pest Manage. Sci. 2000, 56, 875. doi: 10.1002/(ISSN)1526-4998
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