RESEARCH ARTICLE

 

Synthesis and antimicrobial activity of 3-[(4-substituted) (2-oxo-1,3-oxazolidin-3-yl) phosphoryl]-1,3-oxazolidin-2-ones

 

 

Mudumala V.N. Reddy; A.U. Ravi Sankar; B. Siva Kumar; C. Suresh Reddy^*; C. Naga Raju

Department of Chemistry, Sri Venkateswara University, Tirupati-517 502, India

 

 

---

ABSTRACT

3-[(4-Substituted) (2-oxo-1,3-oxazolidin-3-yl)-phosphoryl]-1,3-oxazolidin-2-ones (4a-j) were synthesized through a two-step process. Bis-(2-oxo-1,3-oxazolidin-3-yl)-phosphonic chloride (2) prepared by the reaction of two moles of oxazolidin-2-one (1) with phosphorus oxychloride in dry tetrahydrofuran in the presence of triethylamine and treatment with various heterocyclic aromatic and aliphatic amines under the same experimental conditions afforded the title compounds (4a-j). They were characterized by elemental analysis, IR, NMR (¹H, ¹³C and ³¹P) and mass spectroscopy. Their antimicrobial activities were also evaluated.

Keywords: 3-[(4-Substituted) (2-oxo-1,3-oxazolidin-3-yl)-phosphoryl]-1,3-oxazolidin-2-ones, oxazolidin-2-one, bis-(2-oxo-1,3-oxazolidin-3-yl)-phosphonic chloride, antimicrobial activity, spectral studies

---

 

 

Full text available only in pdf format.

 

Acknowledgements

The authors express their gratitude to Prof. C.D. Reddy, Department of Chemistry, Sri Venkateswara University, Tirupati, for helpful discussions. The Department of Atomic Energy (BRNS, Mumbai, India) is also thanked for providing financial assistance.

 

References and Notes

1 Y.B. Kiran, D. Gunasekar, C.D. Reddy, C.S. Reddy, K. Trank, T. Le, K. Berlin, S. Srinivasan and M.C. Devi. Pest Manage. Sci., 2005, 61, 1016-1023.         [ Links ]

2 (a) Y.L. Nene and P.N. Thapliyal, Fungicides in Plant Disease Control, 2nd edn., IBH Publishing Co, New Delhi, India, 1979, pp. 287-288; (b) S.O. Dulce, J.J. Menn and J.R. Plimmer, A Novel View in Pest Control with Enhanced Environmental Safety. ACS Books, Washington, DC, USA, 1993, p. 1.         [ Links ]

3 D.L. Hill, A Review of Cyclophosphamide, C.C. Thomas, Springfield, IL, USA, 1975.         [ Links ]

4 P.S. Kulkarni, V.N. Gogte, A.S. Modak, S.D. Sahasrabudhe and B.D.Tilak, Org. Mass Spectrom, 1983, 18, 489-493.         [ Links ]

5 G.S. Prasad, B.H. Babu, K.R. Kishore, K. Reddy, P. Haranath and C. S. Reddy, Arkivoc, 2006, 13, 165-170.         [ Links ]

6 Y.H. Babu, P.V.G. Reddy, C.S. Reddy, C.D. Reddy and P.U.M. Devi, J. Heterocyclic Chem., 2002, 39, 1039-1044.         [ Links ]

7 P. Kannan and K. Kishore, Polymer, 1992, 33, 418-422.         [ Links ]

8 P. Kannan, N. Umamaheshwari and K. Kishore, J. Appl. Polym. Sci., 1995, 56, 113-118.         [ Links ]

9 D. Liaw, J. Appl. Polym. Sci, 1997, 65, 59-65.         [ Links ]

10 J.E. Cabrita, X.S. Candeias, A.M. Ramos, C.A.M. Afonso and A. Gilsantos, Tetrahedron Letters, 1999, 40, 137-140.         [ Links ]

11 S.E. Denmark, S. Xiping, Y. Nishigaichi, D.M. Coe, K.-T. Wong, S.B.D. Winter and J.Y. Choi, J. Org. Chem., 1999, 64, 1958-1967.         [ Links ]

12 K. Gholivand, Z. Shariatinia and M. Pourayoubi, Polyhedron, 2006, 25, 711-721.         [ Links ]

13 J. Diago-Meseguer, A.L. Palomo-Coll, J.R. Fernandez-Lizarbe and A.Zugaza-Bilba, Synthesis, 1980, 547-551.         [ Links ]

14 M. Ballestere-Rodes and A.L. Palomo-Coll, Synth. Commun., 1984, 14, 515-520 and references therein.         [ Links ]

15 L.C. Thomas, Interpretation ofthe Infrared Spectra ofOrganophosphorus Compounds, Heyden and Sons, London, UK, 1974.         [ Links ]

16 For an exhaustive approach to SEC techniques see W.W. See Yau, J.J Kirkland and D.D. Bly, Modern Size-exclusion Liquid Chromatography, John Wiley and Sons, New York, NY, USA, 1979.         [ Links ]

17 For an example of the application of MALDI to polymer characterization see: J.B. Williams, A.I Gusev and D.M. Hercules, Macromolecules, 1997, 30, 3781-3787.         [ Links ]

18 R.M. Silverstein and F.X. Webster, Spectrometric Identification of Organic Compounds, 6th edn, John Wiley and Sons, New York, NY, USA, 1998.         [ Links ]

19 N. Muller, P.C. Lauterbur and J. Goldenson, J. Am. Chem. Soc, 1956, 78, 3557-3561.         [ Links ]

20 F. Ramirez, V.A.U. Prasad and J.F. Maracek, J. Am. Chem. Soc, 1979, 96, 7269-7275.         [ Links ]

21 H.J. Benson, Microbiological Applications, 5th edn., W.C. Brown Publications, Boston, MA, USA, 1990, p. 134.         [ Links ]

 

 

Received 10 December 2007
Revised 11 March 2008
Accepted 28 March 2008

 

 

* To whom correspondence should be addressed. E-mail: csrsvu@gmail.com