Citation: Ye Mingyan, Qiu Shaozhong, Yin Guodong. Synthesis of Quinolinone-and Pyridinone-Fused Oxabicyclo[3.3.1]nonanes[J]. Chinese Journal of Organic Chemistry, ;2017, 37(3): 667-674. doi: 10.6023/cjoc201609027 shu

Synthesis of Quinolinone-and Pyridinone-Fused Oxabicyclo[3.3.1]nonanes

Hubei Key Laboratory of Pollutant Analysis and Reuse Technology, College of Chemistry and Chemical Engineering, Hubei Normal University, Huangshi 435002

Corresponding author: Yin Guodong, gdyin@hbnu.edu.cn; gdyin_hbnu@163.com
Received Date: 26 September 2016
Revised Date: 3 November 2016

Fund Project: Project supported by the National Natural Science Foundation of China 21542009

Figures(2)

An efficient and stereoselective synthesis of quinolinone-and pyridinone-fused 2, 8-dioxabicyclo[3.3.1]-nonanes by the reaction of 2-hydroxychalcones with 4-hydroxy-2(1H)-quinolinones/4-hydroxy-2(1H)-pyridinones in refluxing n-PrOH is described. The quinolinone fragment can be converted into the corresponding N-alkylated quinolinones and O-alkylated quinolines by the alkylation reaction. All the unknown compounds are characterized by means of ¹H NMR, ¹³C NMR, IR and HRMS. The structures and configurations of 6-phenyl-2, 12-dihydro-1H-6, 12-methanobenzo[7, 8] [1, 3]dioxocino[5, 4-c]pyri-din-1-one (3r) and 1-isopropoxy-8-phenyl-14H-8, 14-methanobenzo[7, 8] [1, 3]dioxocino[5, 4-c]quinoline (6c) are further confirmed by X-ray single crystal diffraction analysis.
- 4-hydroxy-2(1H)-quinolinone,
- 4-hydroxy-2(1H)-pyridinone,
- bicyclo[3.3.1]nonane,
- alkylation,
- X-ray structure
1. [1]
  Neve, J. E.; Wijesekera, H. P.; Duffy, S.; Jenkins, I. D.; Ripper, J. A.; Teague, S. J.; Campitelli, M.; Garavelas, A.; Nikolakopoulos, G.; Le, P. V.; de A. Leone, P.; Pham, N. B.; Shelton, P.; Fraser, N.; Carroll, A. R.; Avery, V. M.; McCrae, C.; Williams, N.; Quinn, R. J. J. Med. Chem. 2014, 57, 1252. doi: 10.1021/jm401321v
2. [2]
  Zhao, S.; Huang, J.; Cheng, J.; Liu, B.; Chen, C. Chin. J. Org. Chem. 2012, 32, 651 (in Chinese). doi: 10.6023/cjoc1109192
3. [3]
  Banbury, L. K.; Shou, Q.; Renshaw, D. E.; Lambley, E. H.; Griesser, H. J.; Mon H.; Wohlmuth, H. J. Ethnopharmacol. 2015, 163, 251. doi: 10.1016/j.jep.2015.01.033
4. [4]
  Ahsan, M.; Haque, M. R.; Hossain, M. B.; Islam, S. N.; Gray, A. I.; Hasan, C. M. Phytochemistry 2014, 103, 8. doi: 10.1016/j.phytochem.2014.03.008
5. [5]
  Tedesco, R.; Shaw, A. N.; Bambal, R.; Chai, D.; Concha, N. O.; Darcy, M. G.; Dhanak, D.; Fitch, D. M.; Gates, A.; Gerhardt, W. G.; Halegoua, D. L.; Han, C.; Hofmann, G. A.; Johnston, V. K.; Kaura, A. C.; Liu, N.; Keenan, R. M.; Lin-Goerke, J.; Sarisky, R. T.; Wiggall, K. J.; Zimmerman, M. N.; Duffy, K. J. J. Med. Chem. 2006, 49, 971. doi: 10.1021/jm050855s
6. [6]
  Chen, T.; Luo, Y.; Hu, Y.; Yang, B.; Lu, W. Eur. J. Med. Chem. 2013, 64, 613. doi: 10.1016/j.ejmech.2013.04.008
7. [7]
  Detsi, Α.; Bouloumbasi, D.; Prousis, K. C.; Κoufaki, Μ.; Athanasellis, G.; Melagraki, G.; Afantitis, A.; Lgglessi-Markopoulou, O.; Kontogiorgis, C.; Hadjipavlou-Litina, D. J. J. Med. Chem. 2007, 50, 2450. doi: 10.1021/jm061173n
8. [8]
  Nishino, H.; Kumabe, R.; Hamada, R.; Yakut, M. Tetrahedron 2014, 70, 1437. doi: 10.1016/j.tet.2014.01.013
9. [9]
  Lei, M.; Ma, L.; Hu, L. Tetrahedron Lett. 2011, 52, 2597. doi: 10.1016/j.tetlet.2011.03.061
10. [10]
  Pei, W.; Deng, Q.; Wang, H.; Sun L. Chin. J. Org. Chem. 2006, 26, 364 (in Chinese).
11. [11]
  Presset, M.; Coquerel, Y.; Rodriguez, J. Chem. Rev. 2013, 113, 525. doi: 10.1021/cr200364p
12. [12]
  Ruiz, M.; López-Alvarado, P.; Giorgi, G.; Menéndez, J. C. Chem. Soc. Rev. 2011, 40, 3445. doi: 10.1039/c1cs15018a
13. [13]
  Chen, D.; Kuo, P.; Yang, D. Bioorg. Med. Chem. Lett. 2005, 15, 2665. doi: 10.1016/j.bmcl.2005.03.005
14. [14]
  He, Z.; Yang, X.; Jiang, W. Org. Lett. 2015, 17, 3880. doi: 10.1021/acs.orglett.5b01871
15. [15]
  Wang, F.; Chen, F.; Qu, M.; Li, T.; Liu, Y.; Shi, M. Chem. Commun. 2013, 49, 3360. doi: 10.1039/c3cc00295k
16. [16]
  Reddy, G. M.; Sridhar, P. R. Eur. J. Org. Chem. 2014, 1496.
17. [17]
  Xia, L.; Cai, H.; Lee, Y. R. Org. Biomol. Chem. 2014, 12, 4386. doi: 10.1039/c4ob00691g
18. [18]
  Jiang, X.; Song, Z.; Xu, C.; Yao, Q.; Zhang, A. Eur. J. Org. Chem. 2014, 418.
19. [19]
  Srinivas, V.; Koketsu, M. J. Org. Chem. 2013, 78, 11612. doi: 10.1021/jo401990h
20. [20]
  Ganguly, N. C.; Roy, S.; Mondal, P. RSC Adv. 2014, 4, 42078. doi: 10.1039/C4RA05927A
21. [21]
  Yin, G.; Ren, T.; Rao, Y.; Zhou, Y.; Li, Z.; Shu, W.; Wu, A. J. Org. Chem. 2013, 78, 3132. doi: 10.1021/jo400081q
22. [22]
  Rao, Y.; Yin, G. Org. Biomol. Chem. 2013, 11, 6029. doi: 10.1039/c3ob40860d
23. [23]
  Rao, Y.; Liu, M.; Wu, L.; Yin, G. RSC Adv. 2014, 4, 64551. doi: 10.1039/C4RA13166E
24. [24]
  Bingi, C.; Emmadi, N. R.; Chennapuram, M.; Nanubolu, J. B.; Atmakur, K. RSC Adv. 2014, 4, 35009. doi: 10.1039/C4RA07278B
25. [25]
  Yin, G.; Fan, L.; Ren, T.; Zheng, C.; Tao, Q.; Wu, A.; She, N. Org. Biomol. Chem. 2012, 10, 8877. doi: 10.1039/c2ob26642c
26. [26]
  Kinoshita, T.; Nashimoto, A.; Yamamura, Y.; Okamura, T.; Sasako, M.; Sakamoto, J.; Kojima, H.; Hiratsuka, M.; Arai, K.; Sairenji, M.; Fukushima, N.; Kimura, H.; Nakajima, T. Gastric Cancer 2004, 7, 104.
27. [27]
  Luiza, B. D. O.; Borgati, T. F.; de Freitas, R. P.; Ruiz, A. L.; Marchetti, G. M.; de Carvalho, J. E.; da Cunha, E. F. F.; Ramalho, T. C.; Alves, R. B. Eur. J. Med. Chem. 2014, 84, 595. doi: 10.1016/j.ejmech.2014.07.061
28. [28]
  Hao, X.; Xu, Z.; Lu, H.; Dai, X.; Yang, T.; Lin, X.; Ren, F. Org. Lett. 2015, 17, 3382. doi: 10.1021/acs.orglett.5b01628
29. [29]
  Torhan, M. C.; Peet, N. P.; Williams, J. D. Tetrahedron Lett. 2013, 54, 3926. doi: 10.1016/j.tetlet.2013.05.054
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