160 Zhong, Chen, and Zhang
phenyl-1,5-benzothiazepine: light-yellow crystals,
m.p. 165–167ЊC; mmax(cmמ
1) 1610–1578 (Cס
N), 760
(C–S); dH 8.04–6.92 (8H, m, ArH), 4.90–4.62 (1H, m),
REFERENCES
[1] (a) Krapcho, J.; Yale, H. L. U.S. Patent 3,117,124,
1964; Chem Abstr 1964, 60, 8049a; (b) Palmer, P. J.;
Trigg, R. B.; Warrington, J. V. J Med Chem 1971, 14,
248.
[2] (a) Chioccara, F.; Prota, G. Synthesis 1977, 876; (b)
George, B.; Papadopoulos, E. P. J Org Chem 1977, 42,
441; (c) Orlov, V. D.; Kolos, N.; Ruzhitskaya, N. N.
Khim Geterotsikl Soedin 1983, 12, 1638; Chem Abstr
1984, 100, 209766g.
3.14–2.74 (2H, m), 2.24 (3H, s); m/z 363 (M , 1.9),
259 (19), 245 (14), 221 (39), 207 (100), 105 (35), 77
(37); Anal. calcd. for C22H18ClNS: C, 72.61; H, 4.99;
N, 3.85%; found: C, 72.47; H, 5.10; N, 3.62.
6e, 7-Chloro-2,3-dihydro-2-(4Ј-methoxylphenyl)-
4-phenyl-1,5-benzothiazepine: light-yellow crystals,
m.p. 148–150ЊC; mmax(cmמ
1) 1613–1585 (Cס
N), 1250
(ס
C–OMe), 755 (C–S); dH 8.02–6.40 (12H, m), 4.25–
4.05 (1H, m), 3.51 (3H, s), 3.25–2.85 (2H, m); m/z 379
[3] Girard, P.; Namy, J. L.; Kagan, H. B. J Am Chem Soc
1980, 102, 2693.
[4] (a) For reviews see; Krief, A.; Laval, A. M. Chem Rev
1999, 99, 745; (b) Molander, G. A.; Harris, C. R. Tet-
rahedron 1998, 54, 3321; (c) Molander, G. A.; Harris,
C. R. Chem Rev 1996, 96, 307; (d)] Imamota, T. Lan-
thanides in Organic Synthesis; Academic Press: Lon-
don, 1994; Chapter 4; (e) Molander, G. A. Chem Rev
1992, 92, 29; (f) Curran, D. P.; Fevig, T. L.; Jasperse,
C. P.; Totleben, M. J. Synlett 1992, 943.
[5] (a) Zhang, Y.; Lin, R. Synth Commun 1987, 17, 329;
(b) Souppe, D. L.; Namy, J. L.; Kagan, H. B. J Organ-
omet Chem 1983, 250, 227.
[6] (a) Jia, S. X.; Zhang, Y. M. Synth Commun 1994, 24,
387; (b) Zhang, Y. M.; Yu, Y. P.; Lin, R. H. Synth Com-
mun 1993, 23, 189; (c) Fukuzawa, S.; Niiomoto, Y.;
Fujinami, T.; Sakai, S. Heteroat Chem 1990, 1, 490.
[7] Liso, G.; Trapani, G.; Reho, A.; Latrofa, A. Synthesis
1985, 288.
[8] (a) Chikashita, H.; Miyazaki, M.; Itoh, K. J Chem Soc
Perkin Trans 1 1987, 699; (b) Lankelma, H. P.; Shar-
noff, P. X. J Am Chem Soc 1932, 54, 379.
[9] Metzger, J.; Plank, H. Bull Soc Chim Fr 1956, 23,
1692.
[10] Lankelma, H. P.; Sharnoff, P. X. J Am Chem Soc 1931,
53, 2654.
[11] (a) Fujii, K. Yakugaku Zaisshi 1957, 77, 347; Chem
Abstr 1957, 51, 12100h; (b) Santacroce, C.; Sica, D.;
Nicolaus, R. A. Gazz Chim Ital 1968, 98, 85; Chem
Abstr 1968, 69, 36051f.
(M , 1.2), 248 (19), 246 (49), 134 (100); Anal. calcd.
for C22H18ClNOS: C, 69.56; H, 4.78; N, 3.69%; found:
C, 69.44; H, 4.52; N, 3.51.
6f, 7-Chloro-2,3-dihydro-2-(3Ј,4Ј-dioxomethyl-
enephenyl)-4-phenyl-1,5-benzothiazepine: light-yel-
low crystals, m.p. 178–180ЊC; mmax(cmמ
1) 2780, 925,
720 (OCH2O), 1615–1580 (Cס
N), 760 (C–S); dH 8.00–
6.42 (11H, m), 5.77 (2H, s), 4.96–4.62 (1H, m), 3.36–
2.80 (2H, m); m/z 393 (M , 4.2), 289 (23.3), 246
(24.8), 149 (100); Anal. calcd. for C22H16ClNO2S: C,
67.09; H, 4.09; N, 3.56%; found: C, 67.20; H, 3.92; N,
3.43.
6g, 7-Chloro-2,3-dihydro-2-phenyl-4-styryl-1,5-
benzothiazepine: light-yellow crystals, m.p. 102–
104ЊC; mmax(cmמ
1) 1650, 965 (Cס
C), 1615–1582
(Cס
N), 760 (C–S); dH 8.10–6.70 (13H, m), 6.23–5.76
(2H, m), 4.53–4.23 (1H, m), 3.10–2.53 (2H, m); m/z
375 (M , 1.2), 272 (16), 270 (33), 247 (38.6), 245
(100); Anal. calcd. for C23H18ClNS: C, 73.49; H, 4.83;
N, 3.73%; found: C, 73.33; H, 4.76; N, 3.57.
6h, 2,3-Dihydro-4-methyl-2-phenyl-1,5-benzo-
thiazepine: yellow crystals, m.p. 123–124ЊC (lit. [13],
121–123ЊC); mmax(cmמ
1) 2980, 1380 (CH3), 1610–1590
(Cס
N), 758 (C–S); dH 7.82–6.74 (9H, m), 4.70–4.35
(1H, m), 3.10–2.75 (2H, m), 2.03 (3H, s).
[12] Stephens, W. D.; Field, L. Chem Ber 1957, 90, 2683.
[13] Xing, Q.; Jin, S.; Ma, J.; Qi, D. You Ji Hua Xue 1985,
3, 212; Chem Abstr 1985, 105, 24236u.