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Chinese Journal of Organic Chemistry >

2012 , Vol. 32 >Issue 07: 1336 - 1339

DOI: https://doi.org/10.6023/cjoc1111271

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Synthesis and Characterization of 5-phosphonyl 3-arylisoxazoline

  • Zhang Changshui ,
  • Ye Yong
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  • a Chemical Engineering & Pharmaceutics College, Henan University Of Science & Technology, Luoyang 471003;
    b Phosphorus Chemical Engineering Research Center of Henan Province, Department of Chemistry, Zhengzhou University, Zhengzhou 450052

Received date: 2011-11-27

  Revised date: 2011-12-30

  Online published: 2012-03-31

Supported by

Project supported by the National Natural Science Foundation of China (No. 20972143).

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Abstract

A series of regioselectively isoxazolines were synthesized through cycloaddition reaction of nitrile oxides with vinylphosphonate. The structure of title compound was proved as 5-phosphonyl isoxazoline by X-ray crystallography of compound 3c. Their structures were confirmed by NMR, ESI-MS and elemental analysis. We have tested suppression of the NIs, and found they can inhibit neuraminidase.

Key words： Vinylphosphonates; nitrile oxides; 1,3-Dipolar cycloadditions; isoxazoline

Cite this article

Zhang Changshui , Ye Yong . Synthesis and Characterization of 5-phosphonyl 3-arylisoxazoline[J]. Chinese Journal of Organic Chemistry, 2012 , 32(07) : 1336 -1339 . DOI: 10.6023/cjoc1111271

References

[1] Minami, T.; Motoyoshiya, J. Synthesis, 1992, 333
[2] Kumaraswamy, S.; Selvi, R. S.; Swamy, K. C. K. Synthesis, 1997, 207
[3] Tian, L.; Xu, G.Y.; Ye, Y; L-Z Liu, J Heterocyclic Chem, 2003, 1071
[4] Ye, Y.;Luo, Y; Wang, C.F.; Wei, D.Q.; Liu, L.Z.;Zhao, Y.F., Heteroatom Chem., 2009, 20 (2), 95
[5] Ye, Y.; Ma, L.; Luo, Y.; Wang, W.; Liu, L.; Zhao, Y., Phosphorus Sulfur, 2009, 184 (1), 135
[6] Shen, Y.; Jiang, G.F.; Synthesis, 2000, 1, 99
[7]. Wang,T.;Imerhasam,Mukhtar. Chin. J. Org. Chem. 2010,30(12),1831-1839 (in Chinese). (王婷,穆合塔尔·伊米尔艾山,有机化学,2010,30(12),1831-1839
[8]. Zheng,C.Y.;Wu,J.W.;He,,X,W.;Zhang,C.J.;Fan,C.L.;Shang,Y.J.Chin. J. Synth. Chem.2009,17(1),91-94(in Chinese) (郑彩云,吴建伟,何心伟.张传菊,樊陈莉,商永嘉,合成化学,2009,17(1)91-94
[9] Bianchi, G.; Gandolfi, R.; Grunanger P.; Perotti, A. J. Chem. Soc. (C), 1967, 1598.
[10] Sustmann, R.; Huisgen, R.; Huber, H.; Chem. Ber., 1967, 100, 1802.  
[11] Crystallographic data for the structure reported in this article have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-194466. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, U.K
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