W. Zhong, Y. Zhang / Tetrahedron Letters 42 (2001) 3125–3127
3127
4. (a) Develotte, J. Ann. Chim. 1950, 12, 215 (Chem. Abstr.
1951, 45: 1582d); (b) Jacquemin, P. V.; Christiaens, L. E.;
Renson, M. J.; Evers, M. J.; Dereu, N. Tetrahedron Lett.
1992, 33, 3863.
(1.1 mmol) in anhydrous THF (2 mL) was added slowly.
After being stirred for a given time (Table 1, the reaction
was monitored by TLC), the reaction was quenched with
dilute HCl (0.1 mol/L, 3 mL) and extracted with ether
(3×30 mL). The organic phase was successively washed
with a saturated solution of Na2S2O3 (15 mL), saturated
brine (15 mL), and dried over anhydrous Na2SO4. The
solvent was removed under reduced pressure to give the
crude product which was purified by preparative TLC
using ethyl acetate and cyclohexane (1:3) as eluant.
11. Typical physical data of new compounds are listed. Com-
pound 3c, 2-isopropyl-2H-1,4-benzothiazin-3(4H)-one
115–117°C. wmax: 3320 (NH), 2975, 2850, 1380 (CH3,
CH), 1665 (CꢁO) cm−1. lH: 9.80 (1H, br s, NH), 7.32–
6.96 (4H, m, ArH), 3.11 (1H, d, J=7.8 Hz, CH), 2.13–
1.80 (1H, m, CH), 1.04 (6H, d, J=6.5 Hz, 2×CH3). m/z
(%): 208 (M+1, 17), 207 (M+, 71), 165 (100), 164 (41), 136
(60), 132 (71). Anal. C11H13NOS. Calcd C, 63.74; H,
6.32; N, 6.76. Found C, 63.89; H, 6.11; N, 6.53%. Com-
pound 3j, 2-isopropyl-2H-1,4-benzoselenazin-3(4H)-one
123–125°C. wmax: 3335 (NH), 2980, 2830, 1375 (CH3,
CH), 1655 (CꢁO) cm−1. lH: 9.82 (1H, br s, NH), 7.46–
6.95 (4H, m, ArH), 3.20 (1H, d, J=8.0 Hz, CH), 2.15–
1.81 (1H, m, CH), 1.07 (6H, d, J=6.5 Hz, 2×CH3). m/z
(%): 255 (80Se−M+, 100), 253 (78Se−M+, 54.5), 213 (48),
211 (24.6), 184 (25), 132 (87), 83 (87). Anal. C11H13NOSe.
Calcd C, 51.99; H, 5.16; N, 5.51. Found C, 52.12; H,
5.03; N, 5.65%. Compound 3l, 6-chloro-2-methyl-2H-1,4-
benzoselenazin-3(4H)-one 178–180°C. wmax: 3325 (NH),
2960, 2830, 1380 (CH3, CH), 1660 (CꢁO) cm−1. lH: 10.23
(1H, br s, NH), 7.60–6.85 (3H, m, ArH), 3.56 (1H, q,
J=7.2 Hz, CH), 1.53 (3H, d, J=7.2 Hz, CH3). m/z (%):
261 (80Se−M+, 82), 180 (24), 156 (33), 154 (100), 55 (27).
Anal. C9H8ClNOSe. Calcd C, 41.49; H, 3.10; N, 5.38.
Found C, 41.56; H, 3.21; N, 5.14%.
5. Girard, P.; Namy, J. L.; Kagan, H. B. J. Am. Chem. Soc.
1980, 102, 2693.
6. 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.
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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.
7. (a) Zhang, Y.; Lin, R. Synth. Commun. 1987, 17, 329; (b)
Souppe, D. L.; Namy, J. L.; Kagan, H. B. J. Organomet.
Chem. 1983, 250, 227.
8. (a) Jia, S. X.; Zhang, Y. M. Synth. Commun. 1994, 24,
387; (b) Zhang, Y. M.; Yu, Y. P.; Lin, R. H. Synth.
Commun. 1993, 23, 189; (c) Fukuzawa, S.; Niiomoto, Y.;
Fujinami, T.; Sakai, S. Heteroatom. Chem. 1990, 1, 490.
9. (a) Chen, X. Y.; Zhong, W. H.; Zhang, Y. M. J. Chem.
Res. 2000, 386; (b) Chen, X. Y.; Zhong, W. H.; Zhang,
Y. M. Chin. Chem. Lett. 2000, 11, 387; (c) Zhong, W. H.;
Chen, X. Y.; Zhang, Y. M. Heteroatom. Chem. 2001, 12,
in press.
10. General procedure:
A solution of bis(o-nitrophenyl)
disulfides or diselenides (0.5 mmol) in dry THF (3 mL)
was added dropwise to the solution of SmI2 (7 mmol) in
THF (30 mL) at room temperature under a nitrogen
atmosphere. The deep blue color of the solution changed
to yellow (as for bis(o-nitrophenyl) disulfides) or brown-
ish red (as for bis(o-nitrophenyl) diselenides) within 5–10
minutes. Then a solution of a-halocarboxylic derivative
.
.