RESEARCH ARTICLE

 

Straightforward synthesis of a new series of α-(arylamino thiocarbonyloxy) hydrocarbylphosphonates

 

 

Jian-Ping Li^{I, *}; Jun-Ge Zhu^I; Rui-Jie Liu^I; Feng-Ling Cui^I; Ping Liu^II; Guo-Sheng Liu^II

^ICollege of Chemical and Environmental Science, The Key Laboratory of Environmental Pollution Control Technology of Henan Province, Henan Normal University, Xinxiang, 453007, People's Republic of China
^IICollege of Life Sciences, Henan Normal University, Xinxiang, 453007, People's Republic of China

 

 

---

ABSTRACT

A convenient, straightforward, two-step reaction of α-hydroxyhydrocarbylphosphonates with arylisothiocyanates in the presence of catalytic amounts of sodium methoxide in 1,2-dichloroethane as solvent produced various new α-(arylamino thiocarbonyloxy) hydrocarbylphosphonates in excellent yields. Their structures have been confirmed by their IR, ¹H NMR and ³¹P NMR spectra and by elemental analysis. The preliminary antisepsis activity and protein activity of some of the compounds were identified.

Keywords: Phosphonates, arylisothiocyanates, α-hydroxyhydrocarbylphosphonates, synthesis, activity

---

 

 

Full text available only in pdf format.

 

Acknowledgements

We are grateful for financial support from the Natural Science Foundation of the Technology Commission of Henan Province (No. 0611021700).

 

References

1 K.P. Kumar, C. Muthiah, S.K. Swamy and K.C.K. Swamy, Tetrahedron Lett., 2001, 42, 3219-3221.         [ Links ]

2 C. Muthiah, K.P. Kumar, C.A. Mani and K.C.K. Swamy, J. Org. Chem., 2000, 65, 3733-3737.         [ Links ]

3 G.F. Zh and L.T. Li, Pest Trans., 1996,18, 1-3.         [ Links ]

4 K.C.K. Swamy, S. K. Swamy, K.S. Kumar and C. Muthiah, Tetrahedron Lett., 2005,46, 3347-3351.         [ Links ]

5 X.F. Liu and Y. Wang, Chin. J. Appl. Chem, 2005, 22, 40-44.         [ Links ]

6 S. Failla, P. Finocchiaro and G.A. Consiglio, Heteroatom Chem., 2000, 11, 493-504.         [ Links ]

7 H.W. He and Z.J. Liu, Chin. J. Org. Chem., 2001, 21, 878-883.         [ Links ]

8 J.K. Kozlowski, N.P. Rath and C.D. Spilling, Tetrahedron, 1995, 51, 6385-6396.         [ Links ]

9 D.V Petal, K. Rielly-Gauvin and D.E. Ryono, Tetrahedron Lett, 1990, 31, 5587-5590.         [ Links ]

10 H.Schmidt,F.VollenkleandH.Leibigs, Ann. Chem., 1989,12,577-580.         [ Links ]

11 L. Maier, Phosphorus, Sulfur and Silicon, 1993, 76, 119-120.         [ Links ]

12 H.W. He,S.Q. Wang and Z.J. Liu, Chin. J. Appl. Chem, 1998, 15, 89-91.         [ Links ]

13 A.F. Prokofeva, L.P. Gryaznova and N.N. Melnikov, Zh. Obshch. Khhim, 1983, 53, 15.         [ Links ]

14 V.V. Alekseev and N.P. Pokryshchenko, Zh. Obshch. Khim., 1968, 38, 1770-1772.         [ Links ]

15 A.E. Wróblewski and A. Haajewska-Wosik, Tetrahedron: Asymmetry, 2004, 15, 2075-2077.         [ Links ]

16 F. Texier-Boullet and A. Foucaud, Synthesis, 1982, 1, 916-917.         [ Links ]

17 F. Texier-Boullet and A. Foucaud, Synthesis, 1982, 1, 165-166.         [ Links ]

18 F. Texier-Boullet and M. Lequitte, Tetrahedron Lett, 1986, 27, 3515-3516.         [ Links ]

19 X.F. Liu, H.W. He and Q.C. Zhou, Chin. J. Pest. Sci., 2001, 3, 73-75.         [ Links ]

20 E. Joe and W.P. Reeves, J. Org. Chem., 1964, 29, 3098-3099.         [ Links ]

21 R. Pierre-Yves, S. Herve, V. Philippe, L. Eric, D. Sonia and M. Charles, Tetrahedron Lett., 2001, 42, 8479-8481.         [ Links ]

22 R. Pierre-Yves, S. Herve, V. Philippe, J. Ludovic, V. Alain and M. Charles, Chem. - Eur. J., 2002, 8, 2910-2916.         [ Links ]

 

 

Received 30 November 2006
Revised 8 May 2007
Accepted 21 October 2007

 

 

* To whom correspondence should be addressed. E-mail: jplig@163.com