348
A. Ashoorzadeh, V. Caprio
LETTER
(6) (a) Pulz, R.; Cicchi, S.; Brandi, A.; Reißig, H.-U. Eur. J.
References
Org. Chem. 2003, 1153. (b) Cardona, F.; Goti, A.; Brandi,
A. Org. Lett. 2003, 5, 1475. (c) Richichi, B.; Cicchi, S.;
Chiacchio, U.; Romeo, G.; Brandi, A. Tetrahedron 2003, 59,
5231. (d) Pisaneschi, F.; Della Monica, C.; Cordero, F. M.;
Brandi, A. Tetrahedron Lett. 2002, 43, 5711. (e) Cordero,
F. M.; Pisaneschi, F.; Gensini, M.; Goti, A.; Brandi, A. Eur.
J. Org. Chem. 2002, 1941. (f) Goti, A.; Cicchi, S.;
Cacciarini, M.; Cardona, F.; Fedi, V.; Brandi, A. Eur. J. Org.
Chem. 2000, 3633. (g) Zorn, C.; Anichini, B.; Goti, B.;
Brandi, A.; Kozhushkov, S. I.; de Meijere, A.; Citti, L. J.
Org. Chem. 1999, 64, 7846. (h) Goti, A.; Cacciarini, M.;
Cardona, F.; Brandi, A. Tetrahedron Lett. 1999, 40, 2853.
(i) Cardona, F.; Valenza, S.; Picasso, S.; Goti, A.; Brandi, A.
J. Org. Chem. 1998, 63, 7311. (j) Murahashi, S.-I.; Ohtake,
H.; Imada, Y. Tetrahedron Lett. 1998, 39, 2765. (k) Cicchi,
S.; Goti, A.; Brandi, A. J. Org. Chem. 1995, 60, 4743.
(7) (a) Taniguchi, M.; Koga, K.; Yamada, S. Tetrahedron 1974,
30, 3547. (b) Ravid, U.; Silverstein, R. M.; Smith, L. R.
Tetrahedron 1978, 34, 1449.
(1) (a) Koepfli, J. B.; Mead, J. F.; Brockman, J. A. Jr. J. Am.
Chem. Soc. 1947, 69, 1836. (b) Koepfli, J. A.; Mead, J. F.;
Brockman, J. A. Jr. J. Am. Chem. Soc. 1949, 69, 1048.
(2) (a) Jang, C. S.; Fu, F. Y.; Wang, C. Y.; Huang, K. C.; Lu, G.;
Thou, T. C. Science 1946, 103, 59. (b) Hewitt, R. I.;
Wallace, W. S.; Gill, E. R.; Williams, J. H. Am. J. Trop. Med.
Hyg. 1952, 1, 768.
(3) Murata, K.; Takano, F.; Fushiya, S.; Oshima, Y. Biochem.
Pharmacol. 1999, 58, 1593.
(4) (a) Baker, B. R.; Schaub, R. E.; McEvoy, F. J.; Williams, J.
H. J. Org. Chem. 1952, 17, 132. (b) Baker, B. R.; Schaub,
R. E.; McEvoy, F. J.; Williams, J. H. J. Org. Chem. 1953, 18,
153. (c) Baker, B. R.; McEvoy, F. J.; Schaub, R. E.; Joseph,
J. P.; Williams, J. H. J. Org. Chem. 1953, 18, 178.
(d) Baker, B. R.; McEvoy, F. J. J. Org. Chem. 1955, 20, 118.
(e) Baker, B. R.; McEvoy, F. J. J. Org. Chem. 1955, 20, 136.
(f) Hill, R. K.; Edwards, A. G. Chem. Ind. 1962, 858.
(g) Barringer, D. F. Jr.; Beakelhammer, G. B.; Wayne, R. S.
J. Org. Chem. 1973, 38, 1937. (h) Burgess, L. E.; Gross, E.
K. M.; Jurka, J. Tetrahedron Lett. 1996, 37, 3225.
(8) Gmeiner, P.; Dagmar, J. J. Org. Chem. 1995, 60, 3910.
(9) Cicchi, S.; Marradi, M.; Goti Brandi, A. Tetrahedron Lett.
2001, 42, 6503.
(10) Alford, E. J.; Hall, J. A.; Rogers, T. M. A. J. Chem. Soc. C
1966, 1103.
(11) Ranganathan, D.; Rathi, R.; Kesavan, K.; Pal Singh, W.
Tetrahedron 1986, 42, 4873.
(i) Takeuchi, Y.; Hattori, M.; Abe, H.; Harayama, T.
Synthesis 1999, 1814. (j) Kobayashi, S.; Ueno, M.; Suzuki,
R.; Ishitani, H.; Kim, H.-S.; Wataya, S. J. Org. Chem. 1999,
64, 6833. (k) Takeuchi, Y.; Azuma, K.; Takakura, K.; Abe,
H.; Harayama, T. Chem. Commun. 2000, 1643. (l) Okitsu,
O.; Suzuki, R.; Kobayashi, S. Synlett 2000, 989.
(12) Solid N-allylquinazolone 5 (0.34 g, 1.83 mmol) was added
to a solution of nitrone 4 (0.38 g, 1.85 mmol) in toluene. The
mixture was stirred under reflux for 24 h and solvent was
then removed under reduced pressure. The crude product
was purified by column chromatography on silica gel using
Et2O–MeOH 49:1 as eluent to give isoxazolidine 3 as a
colourless oil (0.35 g, 48%). [a]D20 –41.4 (c 1.0, CHCl3). IR
(neat): nmax = 3062, 2944, 1674, 1610 cm–1. 1H NMR (300
MHz, DMSO-d6, 90 °C): d = 1.20–1.32 (m, 1 H), 1.45–1.60
(m, 1 H), 1.64–1.74 (m, 1 H), 2.00 (dddd, 1 H, J = 4.0, 4.0,
4,0, 12.7 Hz), 2.12–2.22 (m, 1 H), 2.24–2.31 (m, 1 H), 2.55–
2.70 (m, 2 H), 3.12 (ddd, 1 H, J = 1.8, 4.0, 4.0 Hz), 3.35–
3.45 (m, 1 H), 4.05 (dd, 1 H, J = 7.5, 13.9 Hz), 4.22 (dd, 1 H,
J = 3.9, 13.9 Hz), 4.39 (m, 1 H), 4.48 (d, 1 H, J = 12.0 Hz),
4.57 (d, 1 H, J = 12.0 Hz), 7.22–7.36 (m, 5 H), 7.54 (ddd, 1
H, J = 1.1, 7.1, 8.1 Hz), 7.67 (d, 1 H, J = 7.7 Hz), 7.81 (ddd,
1 H, J = 1.6, 7.2, 8.5 Hz), 8.20 (dd, 1 H, J = 1.4, 8.1 Hz),
8.22 (s, 1 H). 13C NMR (75 MHz, DMSO-d6, 90 °C): d =
19.8, 27.5, 38.6, 48.4, 51.1, 66.3, 69.5, 72.5, 76.0, 121.0,
125.5, 126.21, 126.5, 126.6, 126.8, 127.4, 133.5, 138.3,
147.4, 147.5, 159.6. HRMS (EI): m/z calcd for
(m) Taniguchi, T.; Ogasawara, K. Org. Lett. 2000, 2, 3193.
(n) Takeuchi, Y.; Azuma, K.; Takakura, K.; Abe, H.; Kim,
H.-S.; Wataya, Y.; Harayama, T. Tetrahedron 2001, 57,
1213. (o) Ooi, H.; Urushibara, A.; Esumi, T.; Iwabuchi, Y.;
Hatakeyama, S. Org. Lett. 2001, 3, 953. (p) Sugiura, M.;
Kobayashi, S. Org. Lett. 2001, 3, 477. (q) Sugiura, M.;
Hagio, H.; Hirabayashi, R.; Kobayashi, S. Synlett 2001,
1225. (r) Okitsu, O.; Suzuki, R.; Kobayashi, S. J. Org.
Chem. 2001, 66, 809. (s) Sugiura, M.; Hagio, H.;
Hirabayashi, R.; Kobayshi, S. J. Am. Chem. Soc. 2001, 123,
12510. (t) Takeuchi, Y.; Harayama, T. Trends Heterocycl.
Chem. 2001, 7, 65. (u) Katoh, M.; Matsune, R.; Nagase, H.;
Honda, T. Tetrahedron 2004, 45, 6221.
(5) (a) Tufariello, J. J.; Asrof Ali, S. Tetrahedron Lett. 1978, 19,
4647. (b) Asrof Ali, S.; Wazeer, M. I. M. J. Chem. Soc.,
Perkin Trans. 1 1988, 597. (c) Carruthers, W.; Moses, R. C.
J. Chem. Soc., Perkin Trans. 1 1988, 2251.
[C23H25N3O3]+: 391.1896. Found: 391.1893.
(13) The specific rotation and spectral data of this compound was
in agreement with the reported values; see ref.4j
Synlett 2005, No. 2, 346–348 © Thieme Stuttgart · New York