SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2013 , Vol. 33 >Issue 05: 1088 - 1095

DOI: https://doi.org/10.6023/cjoc201210034

Notes

A Convenient Synthesis of 3-Aryl-4-fluoroalkyl-2-oxazolidinone

  • Yang Bo ,
  • Zhao Min ,
  • Fang Xiang ,
  • Yang Xueyan ,
  • Wu Fanhong
Expand
  • a School of Chemistry and Molecular Enineering, School of Chemistry and Molecular Enineering, East China University of Science and Technology, Shanghai 200237;
    b School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 200235

Received date: 2012-10-18

  Revised date: 2013-01-21

  Online published: 2013-01-25

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 20972050, 21172148).

Fold

Abstract

An efficient and convenient protocol for the synthesis of 3-aryl-4-fluoroalkyl-2-oxazolidinones is described. The allyl arylcarbamates were obtained from the corresponding aromatic amine and chloroformate allyl ester in high yields. The reaction of allyl arylcarbamates with fluoroalkyl iodide initiated by sodium dithionite in aqueous acetonitrile afforded adducts, which underwent cyclization in the presence of sodium hydride to give corresponding 3-aryl-4-fluoroalkyl-2-oxazolidinone in middle yield. All reactions were carried out in room temperature without phosgene to obtain 3-aryl-4-fluoroalkyl- 2-oxazolidinone. The advantages of this method are that the raw material is easy to get, the operation is simple, it is green and environmental-protection.

Key words： oxazolidin-2-ones; fluorinated alkyl; synthesis; N-cyclizaion

Cite this article

Yang Bo , Zhao Min , Fang Xiang , Yang Xueyan , Wu Fanhong . A Convenient Synthesis of 3-Aryl-4-fluoroalkyl-2-oxazolidinone[J]. Chinese Journal of Organic Chemistry, 2013 , 33(05) : 1088 -1095 . DOI: 10.6023/cjoc201210034

References

[1] Dyen, M. E.; Swern, D. Chem. Rev. 1967, 67, 197.
[2] Tam, W. J. J. Org. Chem. 1986, 51, 2977.
[3] Wouters, J.; Vercauteren, D. P.; Collin, S.; Evrard, G.; Durant, F.; Ducrey, F.; Koenig, J. J.; Jarreau, F. X. Eur. J. Med. Chem. 1992, 27, 939.
[4] Moureau, F.; Wouters, J.; Vercauteren, D. P.; Collin, S.; Evrard, G..; Durant, F.; Ducrey, F.; Koenig, J. J.; Jarreau, F. X. Eur. J. Med. Chem. 1994, 29, 269.
[5] Close, W. J. J. Am. Chem. Soc. 1951, 73, 95.
[6] Kudo, N.; Taniguchi, M.; Furuta, S.; Sato, K.; Endo, T.; Honma, T. J. Agric. Food Chem. 1998, 46, 5305.
[7] Choy, A.; Colbry, N.; Huber, C.; Pamment, M.; Duine, J. V. Org. Process Res. Dev. 1998, 12, 884.
[8] Khalaj, A.; Nakhjiri, M.; Negahbani, A. S.; Samadizadeh, M.; Firoozpour, L.; Rajabalian, S.; Samadi, N.; Faramarzi, M. A.; Adibpour, N.; Shafiee, A.; Foroumadi, A. Eur. J. Med. Chem. 2011, 46, 65.
[9] Selvakumar, N.; Srinivas, D.; Khera, M. K.; Kumar, M. S.; Mamidi, R. N. V. S.; Sarnaik, H.; Charavaryamath, C.; Rao, B. S.; Raheem, M. A.; Das, J.; Iqbal, J.; Rajagopalan, R. J. Med. Chem. 2002, 45, 3953.
[10] Mallesham, B.; Rajesh, B. M.; Reddy, P. R.; Srinivas, D.; Trehan, S. Org. Lett. 2003, 5, 963.
[11] McNulty, J.; Nair, J. J.; Sliwinski, M.; Harrington, L. E.; Pandey, S. Eur. J. Med. Chem. 2007, 5669.
[12] Adam, W.; Bosio, S. G.; Turro, N. J.; Wolff, B. T. J. Org. Chem. 2004, 69, 1704.
[13] Friestad, G. K.; Draghici, C.; Soukri, M.; Qin, J. J. Org. Chem. 2005, 70, 6330.
[14] Yue, X.; Zhang, X.; Qing, F.-L. Org. Lett. 2008, 11, 73.
[15] Masuda, N.; Takahashi, Y.; Otsuki, M.; Ibuki, E.; Miyoshi, H.; Nishino, T. Antimicrob. Agents Chemother. 1996, 40, 1201.
[16] Hoveyda, H. R.; Pinault, J. F. Org. Lett. 2006, 8, 5849.
[17] Ito, H.; Saito, A.; Taguchi, T. Tetrahedron: Asymmetry 1998, 9, 1979.
[18] Cao, Y.; Suzuki, K.; Tajima, T.; Fuchigami, T. Tetrahedron 2005, 61, 6854.
[19] Yang, X. Y.; Fang, X.; Ju, Z. H.; Hu, Y. N.; Wu, F. H. Synthesis 2011, 3627.
[20] Grega, K. C.; Barbachyn, M. R.; Brickner, S. J.; Mizsak, S. A. J. Org. Chem. 1995, 60, 5255.
[21] Huang, W.-Y.; Wang, W.; Huang, B.-N. Acta Chim. Sinica 1985, 43, 409 (in Chinese).
(黄维垣, 王巍, 黄炳南, 中国化学学报, 1985, 43, 409.)
[22] Huang, W.-Y.; Wang, W. Acta Chim. Sinica 1986, 44, 940 (in Chinese).
(黄维垣, 王巍, 中国化学学报, 1986, 44, 940.)
[23] Bertau, M.; Bürlib, M.; Hungerbühlerc, E.; Wagner, P. Tetrahedron: Asymmetry 2001, 12, 2103.
[24] Agami, C.; Couty, F.; Rabasso, N. Tetrahedron Lett. 2000, 41, 4113.
Options
Outlines

/

〈 〉