S. Karabuga et al. / Tetrahedron Letters 46 (2005) 5225–5227
5227
16. Heintzelmann, R. W.; Swern, D. Synthesis 1976, 731–733.
17. Huang, S.; Swern, D. Phosphorus Sulfur 1976, 1, 309–314.
18. Tye, H. Tetrahedron Lett. 2002, 43, 9421–9423.
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Lacote, E.; Malacria, M. Chem. Eur. J. 2004, 10, 906–916.
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Synlett 2002, 116–118.
O
S
Ph
N
O
NQ*
7a
N
O
S
CH2Cl2, HMDS
Ph
10 dr: 1.3:1
OH NHOAc
-78 oC to -10 o
49%
C
21. Cren, S.; Kinahan, T. C.; Skinner, C. L.; Tye, H.
Tetrahedron Lett. 2002, 43, 2749–2751.
9 Q*NHOAc
22. Siu, T.; Yudin, A. K. Org. Lett. 2002, 4, 1839–1842.
23. Siu, T.; Picard, C. J.; Yudin, A. K. J. Org. Chem. 2005, 70,
932–937.
Scheme 4.
24. Atkinson, R. S. Tetrahedron 1999, 55, 1519–1559.
25. Atkinson, R. S.; Fawcett, J.; Claxton, T. A.; Lochrie, I. S.
T.; Ulukanli, S. J. Chem. Soc., Perkin Trans. 2 2002, 819–
828.
but, with virtually no diastereoselectivity (dr: 1.3:1)
(Scheme 4).
26. Atkinson, R. S.; Claxton, T. A.; Lochrie, I. S. T.;
Ulukanli, S. Tetrahedron Lett. 1998, 39, 5113–5116.
27. Atkinson, R. S.; Ayscough, A. P.; Gattrell, W. T.;
Raynham, T. M. J. Chem. Soc., Perkin Trans. 1 1998,
2783–2793.
In conclusion, we have developed a new method for the
conversion of sulfoxides into sulfoximides using
QNHOAc 2. The yields were good in the presence of
HMDS.
28. Atkinson, R. S.; Barker, E.; Ulukanli, S. J. Chem. Soc.,
Perkin Trans. 1 1998, 583–589.
Acknowledgements
29. Ulukanli, S.; Karabuga, S.; Celik, A.; Kazaz, C. Tetrahed-
ron Lett. 2005, 46, 197–199.
30. Al-Sehemi, A. G.; Atkinson, R. S.; Fawcett, J. J. Chem.
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31. Al-Sehemi, A. G.; Atkinson, R. S.; Fawcett, J.; Russell, D.
R. J. Chem. Soc., Perkin Trans. 1 2000, 4413–4421.
32. Al-Sehemi, A. G.; Atkinson, R. S.; Fawcett, J.; Russell, D.
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33. Atkinson, R. S. In Nitrenes and Azides, Reactivity and
Utility; Scriven, E. F. V., Ed.; Academic Press: NewYork,
1984, pp 247–295.
We would like to thank Dr. Ali Gunes for his proofread-
ing of this manuscript. We also thank the Turkish Scien-
tific Research Council (Grant TBAG 2322 (103T071))
for its generous support of this work. We are also grate-
ful to the Department of Chemistry at Ataturk Univer-
sity for the use of the 400 MHz NMR facility and Dr.
Ebru Mete for elemental analyses.
References and notes
34. Typical experimental procedure: 3-Amino-2-ethyl-quinazo-
linone QNH2 1 (0.3 g, 1.58 mmol) and acetic acid-free
lead tetraacetate (LTA) (0.77 g, 1.75 mmol) were added
alternately and continuously in very small portions over
15 min to a vigorously stirred solution of dry dichloro-
methane (6 cm3) at À40 ꢁC. The mixture was then stirred
for a further 5 min to give a solution of the 3-acetoxy-
aminoquinazolinone. The temperature was lowered to
À78 ꢁC, before dropwise addition of the phenyl methyl
sulfoxide (0.44 g, 3.17 mmol) as a solution in dichloro-
methane (3 cm3) containing HMDS (0.51 g, 3.17 mmol)
and then allowing the temperature of the solution to rise
to À10 ꢁC (ꢀ1.5–2 h) with continuous stirring. Saturated
aqueous sodium hydrogen carbonate (30 cm3) was added
and the mixture extracted with dichloromethane
(3 · 30 cm3). The combined organics were washed with
water (3 · 30 cm3), dried with sodium sulfate and the
solvent removed by evaporation under reduced pressure.
The crude product crystallised on addition of ethanol to
give sulfoximide 8a as a colourless solid (0.3 g, 57%), mp
145–147 ꢁC (from ethanol) IR (in CH2Cl2 solution) mmax
cmÀ1: 3479w, 3011w, 2929w, 1675s, 1608w, 1591s and
1568w. 1H NMR (CDCl3, 400 MHz): d 1.35 (3H, t,
J 7.3 Hz, CH2CH3), 3.17 (2H, m, CH2CH3), 3.31 (3H, s,
PhSCH3), 7.39–7.75 (m, 6-H, 7-H, 8-H (Q) and 3H (Ph)),
8.21 (1H, dd, J 8.2 and 1.1 Hz, 5-H (Q)) and 8.33 (2H, dd,
8.4 and 1.7 Hz, 2H (Ph)). 13C NMR (CDCl3, 100 MHz): d
10.8, 28.2, 43.8, 121.3, 126.2, 127.3, 128.8, 129.6, 134.1,
137.3, 146.8, 161.5 and 161.8). Elemental analysis calcu-
lated for C17H17N3O2S: C, 62.36; H, 5.23; N, 12.83; S,
9.79. Found: C, 62.13; H, 5.35; N, 12.97; S, 9.87.
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