8514
Y. Zhou et al. / Tetrahedron Letters 47 (2006) 8511–8514
the scope and limitation of this reaction, and will be
reported in due course.
chloric acid was stirred at 70 ꢀC for 2–4 h. The reaction was
monitored by TLC. After cooling, the mixture was filtered,
and the filtrate was neutralized with NaOH. Water (20 mL)
was added and the solution was extracted with ethyl acetate
(
3 · 10 mL). The combined organic layers were washed
Acknowledgements
with water (2 · 10 mL) and dried with anhydrous Na SO .
2
4
After removal of the solvent, the crude product was purified
by column chromatography (ethyl acetate/petroleum
ether = 1/50, v/v) to give the target compound. These
products 2a–b, 2d–g, 2i–l and 3m–n are known compounds,
which was estimated by H NMR and EI-MS spectrum in
comparison with the reported spectral data. And the
We gratefully acknowledge generous support from the
National Natural Science Foundation of China (Grants
2
0372069, 29725203, and 20472094), the Basic Research
1
Project for Talent Research Group from the Shanghai
Science and Technology Commission, the Key Project
from the Shanghai Science and Technology Commission
spectral data of 2c, 2h and 3j are as follows: Compound
1
(
2c), H NMR (300 MHz, CDCl ): d 8.19–8.27 (2H, m),
3
(
Grant 02DJ14006), the Key Project for New Drug
7
.89 (1H, d, J = 7.8 Hz), 7.73–7.80 (2H, m), 7.68 (1H, d,
Research from CAS.
J = 8.4 Hz), 7.61 (1H, t), 7.54 (1H, d), 7.41 (1H, dd,
+
1
J = 8.1, 1.8 Hz); EI-MS m/z 273 (M ). Compound (2h), H
NMR (300 MHz, CDCl ): d 8.19 (2H, d, J = 8.7 Hz), 7.81
3
References and notes
. Ung, S.; Falguieres, A.; Guy, A.; Ferroud, C. Tetrahedron
(
(
2H, d, J = 8.7 Hz), 7.67–7.76 (3H, m), 7.51 (1H, t), 7.01
+
1H, d, J = 8.4 Hz), 4.33 (4H, s); EI-MS m/z 263 (M ).
1
1
2
Compound (3j), H NMR (300 MHz, DMSO-d ): d 7.80
6
Lett. 2005, 46, 5913–5917.
(1H, d, J = 8.1 Hz), 7.32 (1H, t), 7.19 (1H, d, J = 8.1 Hz),
. Burke, S. D.; Danheiser, R. L. Handbook of Reagents for
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7.01 (1H, t), 5.97 (1H, s), 2.24–2.33 (1H, m), 1.14–1.90
(10H, m); EI-MS m/z 226 (M ).
+
8. Typical procedure for 1k–n preparation: the target com-
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3
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4
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2
2
5
6
7
presence of trimethyl-phosphite was irradiated by a day-
light lamp under nitrogen to give the target compounds.
9. (a) Carey, F. A.; Sundberg, R. J. Advanced Organic
Chemistry Structure and Mechanisms; Springer: New York,
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3
. Brown, R. F. C.; Coulston, K. J.; Eastwood, F. W.; Jurss,
C. J. Aust. J. Chem. 1994, 47, 567–569.
. A mixture of 1.0 mmol of 1a–n and 2.0 mmol of Sn in
2 5
25 mL of C H OH including 4 mL of concentrated hydro-