A Facile One-pot Solid-phase Synthesis of Oxazolidin-2-ones Using Polymer-supported 2-hydroxyalkyl Selenide Reagent

Abstract

A simple, efficient and environmentally friendly procedure for one-pot solid-phase synthesis of 2-oxazolidinones in moderate to good yields by reaction of polystyrene-supported 2-hydroxyalkyl selenide with benzoyl isocyanate and subsequent oxidation/cyclisation-hydrolysis using a selenium traceless linker strategy is described.

Keywords

solid-phase organic synthesis polymer-supported 2-hydroxyalkyl selenide 2-oxazolidinones

References

For recent reviews, see: (a) Shuttleworth

S.J.

, Allin

S.M.

, and Sharma

P.K.

, Synthesis, 1997, 1217; (b) F. Guillier, D.Orain and M. Bradley, Chem. Rev., 2000, 100, 2091; (c) R.E. Sammelson and M.J. Kurth, Chem. Rev., 2001, 101, 137; (d) V. V. Zhdankin and P.J. Stang, Chem. Rev., 2002, 102, 2523.

Danielmeier

, and Steckhan

, Tetrahedron: Asymmetry, 1995, 6, 1181.

Some molecules containing the oxazolidin-2-one moiety have shown interesting pharmaceutical activity. For recent leading references, see: (a) Ahmed

, Adat

, Murrells

, and Owen

C.P.

, Biochem. Biophys. Res. Commun., 2002, 294, 380; (b) A. Mai, M. Artico, M. Esposito, G. Sbardella, S. Massa, O. Befani, P. Turini, V. Giovannini and B. Mondovi, J. Med. Chem., 2002, 45, 1180; (c) M. Seki and K. Mori, Eur. J. Org. Chem., 1999, 64, 2965.

For some recent selected examples of the use of oxazolidin-2-ones as chiral auxiliary, see: (a) Wu

Y.K.

, Shen

, Tang

C.J.

, Chen

Z.L.

, Hu

, and Shi

, J. Org. Chem., 2002, 67, 3802; (b) G. Faita, A. Paio, P. Quadrelli, F. Rancati and P. Senesi, Tetrahedron, 2001, 57, 8313; (c) C. Gaul, K. Scharer and D. Seebach, J. Org. Chem., 2001, 66, 3059; (d) H. Yamamoto, S. Watanabe, K. Kadotani, M. Hasegawa, M. Noguchi and S. Kanemasa, Tetrahedron Lett., 2000, 41, 3131.

(a) Ager

D.J.

, Prakash

, and Schaad

D.R.

, Chem. Rev., 1996, 96, 835. For some recent developments in 2-oxazolidinone synthesis, see: (b) S.C. Bergmeier and S.J. Katz, J. Comb. Chem., 2002, 4, 162; (c) B. Gabriele, R. Mancuso, G. Salerno and M. Costa, J. Org. Chem., 2003, 68, 601; (d) G. Bartoli, M. Bosco, A. Carlone, M. Locatelli, P. Melchiorre and L. Sambri, Org. Lett., 2005, 7, 1983.

(a) Paulmier

C. Ed.

, Selenium Reagents and Intermediates in Organic Synthesis, Pergamon Press: Oxford, 1986; (e) D. Liotta, Ed. Organoselenium Chemistry, Wiley: New York, 1987; (f) A. Krief, Comprehensive Organic Synthesis, Pergamon: Oxford, 1991; (g) T.G. Back, Organoselenium Chemistry, Oxford University Press: Oxford, 1999; (h) T. Wirth, Organoselenium Chemistry, Springer: Berlin, 2000.

(a) Nicolaou

K.C.

, Pastor

, Barluenga

, and Winssinger

, Chem. Commun., 1998, 1947; (b) T. Ruhland, K. Andersen and H. Pedersen, J. Org. Chem., 1998, 63, 9204; (c) K.-I. Fujita, S. Hashimoto, A. Oishi and Y. Taguchi, Tetrahedron Lett., 2003, 44, 3793; (d) L. Uehlin and T. Wirth, Org. Lett., 2001, 3, 2931.

(a) Huang

, and Sheng

S.-R.

, Tetrahedron Lett., 2001, 42, 9035; (b) X. Huang and S.-R. Sheng, J. Comb. Chem., 2003, 5, 273; (c) S.-R. Sheng, X.-L. Liu, X.-C. Wang, Q. Xin and C.-S. Song, Synthesis, 2004, 2833; (d) X.-L. Liu, S.-R. Sheng, Q.-Y. Wang, W.-K. Sun, Q. Xin and H.-Y. Ao, J. Chem. Res(S)., 2006, 118; (e) B. Huang, S.-R. Sheng, Y.-X. Huang, Q. Xin, L.-Y. Song and N.-H. Luo, J. Chem. Res(S)., 2006, 623.

Zundel

, Angew. Chem., Int. Ed. Engl., 1969, 8, 499.

10.

(a) Ferranti

, and Filippo

D.D.

, J. Chem. Soc. (B)., 1971, 1925; (b) W.-M. Xu, E. Tang and X. Huang, Synthesis, 2004, 2094.

11.

Hassner

, Lorber

M.E.

, and Heathcock

, J. Org. Chem., 1967, 32, 540.