X. Fan, Y. Zhang / Tetrahedron Letters 43 (2002) 7001–7003
7003
3. Michael, J. P. Nat. Prod. Rep. 1997, 14, 605 and refer-
ences cited therein.
4. Walsh, D. A. Synthesis 1980, 677.
5. Jones, G. In Comprehensive Heterocyclic Chemistry II;
Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.;
Pergamon Press: Oxford, 1996; Vol. 5, Chapter 5.05, p.
167.
g, 1 mmol) in dry THF (20 mL) was stirred at room
temperature until the samarium disappeared. To the
resulting dark blue suspension of SmI2 was added 3-aryl-
2,1-benzisoxazole (0.5 mmol). The mixture was stirred at
room temperature for 5 min. On completion, the reaction
mixture was poured into H2O (10 mL) and extracted with
ethyl acetate (3×15 mL). The combined extracts were
6. (a) Konwar, D.; Boruah, R. C.; Sandhu, J. S. Chem. Ind.
1989, 191; (b) Dutta, D. K.; Konwar, K. Indian J. Chem.
1994, 33B, 690; (c) Okabe, M.; Sun, R. C. Tetrahedron
1995, 51, 1861.
7. (a) Arcadi, A.; Marinelli, F.; Rossi, E. Tetrahedron 1999,
55, 13233; (b) Amaresh, R. R.; Perumal, P. T. Tetra-
hedron 1998, 54, 14327; (c) Katritzky, A. R.; Semenzin,
D.; Yang, B.; Pleynet, D. P. M. J. Heterocyclic Chem.
1998, 35, 467; (d) Mahanty, J. S.; De, M.; Das, P.;
Kundu, N. G. Tetrahedron 1997, 53, 13397.
washed subsequently with
a saturated solution of
Na2S2O3 (15 mL) and a saturated solution of NaCl (15
mL) and dried over anhydrous Na2SO4. After evaporat-
ing the solvent under reduced pressure, the crude product
was purified by preparative TLC on silica gel using ethyl
acetate–cyclohexane (1:4) as eluent to yield the corre-
sponding 2-aminobenzophenones. All the 2-aminoben-
zophenones are known compounds and have physical
1
data (mp) and spectral characteristics (IR and H NMR)
in agreement with those of the known compounds.
17. Typical procedure for the preparation of 5-chloro-2-(4-
methylphenyl)-4-phenylquinoline (4b): To a dark blue
suspension of SmI2 (1 mmol) in THF was added 3-
phenyl-5-chloro-2,1-benzisoxazole (0.12 g, 0.5 mmol).
The mixture was stirred at room temperature for 5 min.
Then, to the reaction mixture was added 4%-methylace-
tophenone (0.72 g, 0.6 mmol). Stirring was continued for
another hour. On completion, the reaction mixture was
poured into H2O (15 mL) and extracted with diethyl
ether (3×15 mL). The combined extracts were washed
with a saturated solution of Na2S2O3 (15 mL) and a
saturated solution of NaCl (15 mL) and dried over
anhydrous Na2SO4. After evaporating the solvent under
reduced pressure, the crude product was purified by
preparative TLC on silica gel using ethyl acetate–cyclo-
hexane (1:8) as eluent to yield 4b (66%), mp 132–134°C;
1H NMR (400 MHz, CDCl3): l 8.20 (d, 1H, J=8.0 Hz),
8.09 (d, 2H, J=8.0 Hz), 7.85 (d, 1H, J=3.5 Hz), 7.82 (s,
1H), 7.67–7.64 (m, 1H), 7.57–7.52 (m, 5H), 7.33 (d, 2H,
J=8.0 Hz), 2.43 (s, 3H); 13C NMR (100 MHz, CDCl3): l
21.4, 119.9, 124.5 126.5, 127.4 128.7, 128.8 129.5, 129.6,
130.4, 131.7, 131.9, 136.4, 137.9, 139.8, 147.3, 148.3,
157.1; MS m/z (%): 329 (M+, 100), 294 (23). Anal. calcd
for C22H16ClN: C, 80.11; H, 4.89; N, 4.25. Found: C,
80.25; H, 4.78; N, 4.33%. Other 2,4-diarylquinoline
derivatives were obtained in a similar manner and were
8. For reviews, see: (a) Krief, A.; Laval, A. M. Chem. Rev.
1999, 99, 745; (b) Molander, G. A. Acc. Chem. Res. 1998,
31, 603; (c) Molander, G. A.; Harris, C. R. Tetrahedron
1998, 54, 3321; (d) Molander, G. A.; Harris, C. R. Chem.
Rev. 1996, 96, 307; (e) Imamota, T. Lanthanides in
Organic Synthesis; Academic Press: London, 1994; Chap-
ter 4; (f) Molander, G. A. Chem. Rev. 1992, 92, 29; (g)
Curran, D. P.; Fevig, T. L.; Jasperse, C. P.; Totleben, M.
J. Synlett 1992, 943.
9. (a) Souppe, J.; Danon, L.; Namy, J. L.; Kagan, H. B. J.
Organomet. Chem. 1983, 250, 227; (b) Zhang, Y. M.; Lin,
R. H. Synth. Commun. 1987, 17, 329; (c) Mukaiyama, T.;
Yoyozu, K.; Kato, K.; Yamada, T. Chem. Lett. 1982,
181; (d) Kende, A. S.; Mendoza, J. S. Tetrahedron Lett.
1991, 32, 1699.
10. Natale, N. R. Tetrahedron Lett. 1982, 23, 5009.
11. Sternbach, L. H.; Reeder, E.; Keller, O.; Metlesics, W. J.
Org. Chem. 1961, 26, 4480.
12. Walker, G. N. J. Org. Chem. 1962, 27, 1929.
13. Bortolotti, B.; Leardini, R.; Nannl, D.; Zanarkl, G. Tet-
rahedron 1993, 49, 10157.
14. Leardini, R.; Nanni, D.; Pedulli, G. F.; Tundo, A.;
Zanardi, G. J. Chem. Soc., Perkin Trans. 1 1986, 1591.
15. 3-Aryl-2,1-benzisoxazoles were conveniently prepared
according to the literature. See: Davis, R. B.; Pizzini, L.
C. J. Org. Chem. 1960, 25, 1884.
16. General procedure for the preparation of 2-aminoben-
zophenones (2): Under anhydrous conditions, a mixture
of powdered samarium (0.15 g, 1 mmol) and iodine (0.25
1
also fully characterized by IR, H NMR, 13C NMR, MS
and elemental analysis.