Akbar MOBINIKHALEDI, Naser FOROUGHIFAR, Zahra KALATE

Synthesis of Some New Isoxazolidines by 1,3-Dipolar Cycloaddition Reaction of Nitrones and Olefins

A series of new isoxazolidines 5a-j were synthesized by 1,3-dipolar cycloaddition reaction of different nitrones with substituted olefins under reflux condition. The yields of products following recrystallization from absolute ethanol were of the order of 40%-66%. IR, NMR and mass spectroscopies were used for identification of these compounds.

Anahtar Kelimeler:

Isoxazolidine, Nitrones, 1, 3-Dipolar, Cycloaddition

Synthesis of Some New Isoxazolidines by 1,3-Dipolar Cycloaddition Reaction of Nitrones and Olefins

Keywords:

Isoxazolidine, Nitrones, 1, 3-Dipolar, Cycloaddition,

PDF

___

G.R. Delpierre and M. Lamchen, Quqrt. Rev, 19, 329 (1965).
J. Hamer and A. Macaluso, Chem. Rev, 64, 473 (1964).
R. Huisgen, Angew. Chem. Int. Ed. Engl, 2, 565 (1963).
K. Hensley, J.M. Carney, C.A. Stewart, T. Tabafabaie, Q. Pye and R.A. Floyd, Int. Rev. Neurobiol, 40, (1999).
D.S.C. Black, R.F. Crozier and V.C. Davis, Synthesis, 205 (1975).
J.P. Freeman, Chem. Rev, 83, 241 (1983).
R.H.D. Barton and J.M. Beaton, J. Am. Chem. Soc, 82, 2641 (1960).
S.R. Sandler and W. Karo, Organic Functional Group Preparations, 2nd ed, Academic Press, San Diego, Vol 3, pp. 351-376 (1989).
H. Mitsui, S. Zenki, T. Shiota, and S-I. Murahashi, J. Chem. Soc. Chem. Commun, 874 (1984).
S. Cicchi, M. Corsi and A. Goti, J. Org. Chem, 64, 7243 (1999).
R.W. Murray and M. Singh, J. Org. Chem, 55, 2954 (1990).
W.W. Zajac.Jr., T.R. Walters and M.G. Darcy, J. Org. Chem, 53, 5856 (1988).
S-I. Murahashi, T. Shiota and Y. Imada., Org. Synth, 70, 265 (1991).
A.H. Fenselau, E.H. Hamamura and J.G. Moffatt, J. Org. Chem, 35, 3546 (1970).
M. Nojima, K. Takeuchi, E. Fukui and N. Tokura, J. Che. Soc; Perkin. Trans, 1, 2202 (1976).
P.A.S. Smith and S.E. Gloyer, J. Org. Chem, 40, 2508 (1975).
S-I. Murahashi, H. Mitsui, T. Shiota, T. Tsuda and S.J. Watanabe, J. Org. Chem, 55, 1736 (1990).
S. Yamazaki, Bull. Chem. Soc. Jpn, 70, 877 (1997).
P.C. Dennis, Advances in Cycloaddition, Vol 3, 1993.
D.P.A. Iannazzo, V. Pistara, A. Rescifina and R. Romeo. Tetrahedron, 58, 581 (2002).
A. Banerji and P. Sengupta, J. Indian Inst. Sci, 81, 313 (2000).