Citation: Yang Quanli, Song Yuye, Yu Ping, Wang Long, Liu Mingguo, Huang Nianyu. 1, 8-Diazabicyclo[5.4.0]undec-7-ene (DBU)-Promoted Stere-oselective Synthesis of Oxazolidin-2-(thi)one Derivatives[J]. Chinese Journal of Organic Chemistry, ;2017, 37(12): 3177-3185. doi: 10.6023/cjoc201704036 shu

1, 8-Diazabicyclo[5.4.0]undec-7-ene (DBU)-Promoted Stere-oselective Synthesis of Oxazolidin-2-(thi)one Derivatives

Yang Quanli ^a ,
Song Yuye ^a ,
Yu Ping ^a ,
Wang Long ^b ,
Liu Mingguo ^a ,
Huang Nianyu ^a,,

a.
Hubei Key Laboratory of Natural Products Research and Development, College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang 443002
b.
College of Materials and Chemical Engineering, China Three Gorges University, Yichang 443002

Corresponding author: Huang Nianyu, hny115@126.com
Received Date: 21 April 2017
Revised Date: 10 August 2017
Available Online: 8 December 2017
Fund Project: the National Natural Science Foundation of China 21602123Project supported by the National Natural Science Foundation of China (No. 21602123), the Youth Talent Development Foundation and Scientific Foundation from Graduate School of China Three Gorges University (No. SDYC2016121)the Youth Talent Development Foundation and Scientific Foundation from Graduate School of China Three Gorges University SDYC2016121

Figures(4)

A series of multi-substituted oxazolidin-2-(thi)one derivatives were prepared via 1, 8-diazabicyclo[5.4.0]undec-7-ene (DBU) promoted nucleophilic addition/cyclization from alkynyl alcohol and isocynate or thiocynate in high yields of 75%~95%. This concise and efficient approach provides a facial access to a library of biological (Z)-arylmethylene substituted oxazolidin-2-(thi)one derivatives with high stereo-selectivities.
- oxazolidin-2-(thi)one,
- 1, 8-diazabicyclo[5.4.0]undec-7-ene (DBU),
- stereo-selectivity
1. [1]
  Zappia, G.; Menendez, P.; Monache, G. D.; Misiti, D.; Nevola, L.; Botta, B. Mini-Rev. Med. Chem. 2007, 7, 389. doi: 10.2174/138955707780363783
2. [2]
  (a) Phillips, O. A.; Sharaf, L. H. Expert Opin. Ther. Pat. 2016, 26, 591.
  (b) Jadhavar, P. S.; Vaja, M. D.; Dhameliya, T. M.; Chakraborti, A. K. Curr. Med. Chem. 2015, 22, 4379.
3. [3]
  (a) Fujita, T.; Yamago, S. Chem.-Eur. J. 2015, 21, 18547.
  (b) Green, R.; Peed, J.; Taylor, J. E.; Blackburn, R. A.; Bull, S. D. Nat. Protoc. 2013, 8, 1890.
4. [4]
  Ferreira, J.; Rees-Jones, S. C.; Ramaotsoa, V.; Msutu, A.; Hunter, R. Org. Biomol. Chem. 2016, 14, 1545. doi: 10.1039/C5OB02560E
5. [5]
  (a) Guo, B.; Fan, H.; Xin, Q.; Chu, W.; Wang, H.; Huang, Y.; Chen, X.; Yang, Y. J. Med. Chem. 2013, 56, 2642.
  (b) Friggeri, L.; Ballante, F.; Ragno, R.; Musmuca, I.; De Vita, D.; Manetti, F.; Biava, M.; Scipione, L.; Di Santo, R.; Costi, R.; Feroci, M.; Tortorella, S. J. Chem. Inf. Model. 2013, 53, 1463.
6. [6]
  (a) Njiojob, C. N.; Bozell, J. J.; Long, B. K.; Elder, T.; Key, R. E.; Hartwig, W. T. Chem.-Eur. J. 2016, 22, 12506.
  (b) Mydock-McGrane, L.; Rath, N. P.; Covey, D. F. J. Org. Chem. 2014, 79, 5636.
7. [7]
  Mendes, R. E.; Deshpande, L. M.; Jones, R. N. Drug Resist. Updates 2014, 17, 1. doi: 10.1016/j.drup.2014.04.002
8. [8]
  Chahine, E. B.; Sucher, A. J.; Knutsen, S. D. Consult. Pharm. 2015, 30, 386. doi: 10.4140/TCP.n.2015.386
9. [9]
  (a) Xu, J. X.; Zhao, J. W.; Jia, Z. B. Chin. Chem. Lett. 2011, 22, 1063.
  (b) Li, Y. W.; Liu, Y.; Jia, Y. C.; Yuan, J. Y. Chin. Chem. Lett. 2013, 24, 230.
10. [10]
  (a) Sadeghzadeh, S. M. Appl. Organomet. Chem. 2016, 30, 835.
  (b) Bacchi, A.; Chiusoli, G. P.; Costa, M.; Gabriele, B.; Righi, C.; Salerno, G. Chem. Commun. 1997, 1209.
  (c) Song, Q. W.; Zhou, Z. H.; Wang, M. Y.; Zhang, K.; Liu, P.; Xun, J. Y.; He, L. N. ChemSusChem 2016, 9, 2054.
  (d) Hu, J.; Ma, J.; Zhu, Q.; Zhang, Z.; Wu, C.; Han, B. Angew. Chem., Int. Ed. 2015, 54, 5399.
  (e) Hase, S.; Kayaki, Y.; Ikariya, T. ACS Catal. 2015, 5, 5135.
11. [11]
  (a) Fujisaki, F.; Abe, N.; Sumoto, K. Heterocycles 2008, 75, 1681.
  (b) Steiner, B.; Langer, V.; Koóš, M. Carbohydr. Res. 2009, 344, 2079.
12. [12]
  a) Li, S. Q.; Xiong, P.; Zhu, L.; Qian, X. Y.; Xu, H. C. Eur. J. Org. Chem. 2016, 2016, 3449.
  (b) Sekine, K.; Mawatari, T.; Yamada, T. Synlett 2015, 26, 2447.
  (c) Kim, W. S.; Yoon, E.; Jo, K. A.; Kang, E. J. Bull. Korean Chem. Soc. 2011, 32, 3158.
13. [13]
  (a) Lu, X. F.; Yang, Z.; Huang, N. Y.; He, H. B.; Deng, W. Q.; Zou, K. Bioorg. Med. Chem. Lett. 2015, 25, 3726.
  (b) Wang, L.; Xie, Y. B.; Huang, N. Y.; Yan, J. Y.; Hu, W. M.; Liu, M. G.; Ding, M. W. ACS Catal. 2016, 6, 4010.
  (c) Li, R. K.; Yang, Q. L.; Liu, Y.; Li, D. W.; Huang, N. Y.; Liu, M. G. Chin. Chem. Lett. 2016, 27, 345.
14. [14]
  Li, S.; Ye, J.; Yuan, W.; Ma, S. Tetrahedron 2013, 69, 10450. doi: 10.1016/j.tet.2013.09.087
15. [15]
  Zhao, J.; Huang, H.; Qi, C.; Jiang, H. Eur. J. Org. Chem. 2012, 29, 5665.
16. [16]
  (a) Ritter, S.; Horino, Y.; Lex, J.; Schmalz, H. G. Synlett 2006, 3309.
  (b) Ramesh, R.; Chandrasekaran, Y.; Megha, R.; Chandrasekaran, S. Tetrahedron 2007, 63, 9153.
  (c) Hu, M.; Song, R. J.; Li, J. H. Angew. Chem., Int. Ed. 2015, 54, 608.
17. [17]
  (a) Doherty, S.; Knight, J. G.; Perry, D. O.; Ward, N. A.; Bittner, D. M.; McFarlane, W.; Probert, M. R. Organometallics 2016, 35, 1265.
  (b) Wang, F.; Wang, Y.; Cai, L.; Miao, Z.; Chen, R. Adv. Synth. Catal. 2008, 350, 2733.
  (c) Hu, Y.; Xin, X.; Wan, B. Tetrahedron Lett. 2014, 55, 32.
18. [18]
  (a) Hashmi, A.; Stephen K.; Wang, T.; Shi, S.; Rudolph, M. J. Org. Chem. 2012, 77, 7761.
  (b) Engel, D. A.; Dudley, G. B. Org. Lett. 2006, 8, 4027.
  (c) Jagtap, S. R.; Bhanage, B. M. J. Chem. Res. 2007, 6, 370.
  (d) Smissman, E. E.; Johnsen, R. H.; Carlson, A. W.; Aycock, B. F. J. Org. Chem. 1956, 78, 3395.
  (e) Cooper, M. A.; Lucas, M. A.; Taylor, J. M.; Ward, A. D.; Williamson, N. M. Synthesis 2001, 621.
  (f) Moran, W. J.; Rodríguez, A. Org. Biomol. Chem. 2012, 10, 8590.
  (g) Zhang, H.; Tanimoto, H.; Morimoto, T.; Nishiyama, Y.; Kakiuchi, K. Org. Lett. 2013, 20, 5222.
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