F. L. Ansari et al. / Bioorg. Med. Chem. 16 (2008) 7691–7697
7695
5.2.3.1. 2-(Phenyl)-4-(30-hydroxyphenyl)-2,3-dihydro-1,5-ben-
zothiazepine (27). Yield 71%; mp 102 °C; 1H NMR (DMSO-d6): d
8.60 (s, 1H, OH), 6.93–7.70 (m, 13H, aryl H), 4.16 (dd,
J2,3a = 5.0 Hz, J2,3b = 12.0 Hz, 1H, H-2), 3.23 (dd, J3a,3b = 12.0 Hz,
5.2.3.9. 2-(300-Hydroxyphenyl)-4-(30-hydroxyphenyl)-2,3-dihydro-1,
5-benzothiazepine (35). Yield 70%; mp 142 °C dec; 1H NMR
(DMSO-d6): d 8.89 and 8.63 (s, 2H, OH), 6.87–8.06 (m, 12H, aryl
H), 3.85 (d, J2,3b = 6.3 Hz, 1H, H-2), 3.34 (unresolved, 1H, H-3a),
J
3a,2 = 5.0 Hz, 1H, H-3a), 2.53 (t, J3b,3a = J3b,2 = 12.0 Hz, 1H, H-3b);
2.41 (d, J d 157.0 (C-4),
3b,2 = 6.3 Hz, 1H, H-3b); 13C NMR:
13C NMR: d 160.0 (C-4), 113.0–157.9 (aryl C), 45.5 (C-2), 28.2 (C-
3); EIMS (m/z, %): 330 [M+Å, 6].
113.0–157.9 (aryl C), 45.5 (C-2), 28.2 (C-3); EIMS (m/z, %): 347
[M+Å, 9].
5.2.3.10. 2-(400-Hydroxyphenyl)-4-(30-hydroxyphenyl)-2,3-dihydro-
1,5-benzothiazepine (36). Yield 53%; mp 170–172 °C; 1H NMR
(DMSO-d6): d 8.71 and 8.49 (s, 2H, OH), 6.76–8.00 (m, 12H, aryl
H), 3.58 (t, J2,3a = J2,3b = 7.2 Hz, 1H, H-2), 3.06 (unresolved, 1H, H-
3a), 2.87 (unresolved, 1H, H-3b); 13C NMR: d 157.1 (C-4), 113.0–
147.0 (aryl C), 40.2 (C-2), 28.0C-3; EIMS (m/z, %): 347 [M+Å, 8].
5.2.3.2. 2-(200-Chlorophenyl)-4-(30-hydroxyphenyl)-2,3-dihydro-
1,5-benzothiazepine (28). Yield 81%; mp 45–47 °C; 1H NMR
(DMSO-d6): d 10.05 (s, 1H, OH), 7.09–8.43 (m, 12H, aryl H), 4.89
(dd, J2,3a = 5.1 Hz, J2,3b = 9.0 Hz, 1H, H-2), 3.43 (dd, J3b,3a = 14.0 Hz,
J
3b,2 = 9.0 Hz, 1H, H-3b), 3.36 (dd, J3a,3b = 14.0 Hz, J3a,2 = 5.1 Hz,
1H, H-3a); 13C NMR: d 167.5 (C-4), 115.2–162.2 (aryl C), 55.9 (C-
2), 27.2 (C-3); EIMS (m/z, %): 367 [M+Å+2, 3], 366 [M+Å+1, 1], 365
[M+Å, 9].
00
0
5.2.3.11. 2-(2 -Methoxyphenyl)-4-(3 -hydroxyphenyl)-2,3-dihydro-1,
5-benzothiazepine (37). Yield 61%; mp 62–64 °C; 1H NMR (d6-
acetone): d 8.11 (s, 1H, OH), 7.04–8.08 (m, 12H, aryl H), 3.58 (t,
5.2.3.3. 2-(300-Chlorophenyl)-4-(30-hydroxyphenyl)-2,3-dihydro-
1,5-benzothiazepine (29). Yield 80%; mp 100–101 °C; 1H NMR
(DMSO-d6): d 10.0 (s, 1H, OH), 7.10–8.03 (m, 12H, aryl H), 4.32
J
2,3b = 6.9 Hz, 1H, H-2), 2.87 (unresolved, 1H, H-3a*), 2.50 (s, 3H,
O-CH3), 1.036 (t, J3b,2 = 6.9 Hz, 1H, H-3b*); 13C NMR: d 162.7 (C-
4), 114.0–158.3 (aryl C), 56.0 (O-CH3), 43.0 (C-2), 40.2 (C-3); EIMS
(m/z, %): 361[M+Å, 5].
(dd, J2,
J2,3a = 5.0 Hz, J3b = 12.9 Hz, 1H, H-2), 3.74 (t, J3b,3a =
J
3b,2 = 12.6 Hz, 1H, H-3b), 3.51 (dd, J3a,3b = 12.9 Hz, J3a,2 = 5.0 Hz,
1H, H-3a); 13C NMR: d 165.0 (C-4), 118.0–158.7 (aryl C), 56.3 (C-
2), 33.5 (C-3); EIMS (m/z, %): 367 [M+Å+2, 2], 366 [M+Å+1, 1], 365
[M+Å, 6].
5.2.3.12. 2-(300-Methoxyphenyl)-4-(30-hydroxyphenyl)-2,3-dihydro-1,
5-benzothiaze-pine (38). Yield 59%; mp 58 °C; 1H NMR (d6-ace-
tone): d 8.63 (s, 1H, OH), 6.77–7.31 (m, 12H, aryl H), 3.41 (d,
5.2.3.4. 2-(400-Chlorophenyl)-4-(30-hydroxyphenyl)-2,3-dihydro-
1,5-benzothiazepine (30). Yield 87%; mp 114 °C; 1H NMR (DMSO-
d6): d 10.05 (s, 1H, OH), 7.09–8.44 (m, 12H, aryl H), 5.0 (dd,
J
2,3b = 7.1 Hz, 1H, H-2), 3.0 (unresolved, 1H, H-3a), 2.76 (s, 3H, O-
CH3), 1.65 (d, J3b,2 = 7.1 Hz, 1H, H-3b); 13C NMR: d 161.6 (C-4),
115.0–158.0 (aryl C), 57.0 (O-CH3), 41.7 (C-2), 39.0 (C-3); EIMS
(m/z, %): 361 [M+Å, 8].
J
2,3a = 5.1 Hz, J2,3b = 12.9 Hz, 1H, H-2), 3.53 (t, J3b,3a = J3b,2 = 12.9 Hz,
1H, H-3b), 3.39 (dd, J3a,3b = 12.9 Hz, J3a,2 = 5.1 Hz, 1H, H-3a); 13C
NMR: d 160.0 (C-4), 113.0–157.9 (aryl C), 45.5 (C-2), 28.2 (C-3);
EIMS (m/z, %): 367 [M+Å+2, 3], 366 [M+Å+1, 1], 365 [M+Å, 10].
5.2.3.13. 2-(400-Methoxyphenyl)-4-(30-hydroxyphenyl)-2,3-dihydro-
1,5-benzothiazepine (39). Yield 56%; mp 80 °C; 1H NMR (d6-ace-
tone): d 9.10 (s, 1H, OH), 6.23–7.09 (m, 12H, aryl H), 3.83 (s, 3H,
O-CH3), 3.30 (d, J2,3b = J = 7.0 Hz, 1H, H-2), 2.9 (unresolved, 1H, H-
3a*), 1.0 (t, J3b,3a = J3b,2 = 6.9 Hz, 1H, H-3b*); 13C NMR: d 159.6 (C-
4), 114.7–158.0 (aryl C), 59.0 (O-CH3), 43.5 (C-2), 40.0 (C-3); EIMS
(m/z, %): 361 [M+Å, 10].
5.2.3.5. 2-(200-Fluorophenyl)-4-(30-hydroxyphenyl)-2,3-dihydro-
1,5-benzothiazepine (31). Yield 87%; mp 68–70 °C; 1H NMR
(DMSO-d6): d 9.72 (s, 1H, OH), 6.96–7.59 (m, 12H, aryl H), 5.31
(dd, J2,3b = 12.6 Hz, J2,3a = 9.9 Hz, 1H, H-2), 3.36 (dd, J
=
3a,3b
12.6 Hz, J3a,2 = 9.9 Hz, 1H, H-3a), 2.87 (t, J3b,2 = J3b,3a = 12.6 Hz,
1H, H-3b); 13C NMR: d 168.9 (C-4), 114.0–160.6 (aryl C), 53.3 (C-
2), 35.3 (C-3); EIMS (m/z, %): 349 [M+Å, 7].
5.2.3.14. 2-(300,400-Dimethoxyphenyl)-4-(30-hydroxyphenyl)-2,3-
dihydro-1,5-benzo-thiazepine (40). Yield 61%; mp 96 °C; 1H NMR
(d6-acetone): d 9.7 (s, 1H, OH), 6.46–7.15 (m, 12H, aryl H), 3.80 and
3.77 (s, 3H, 300, 400O-CH3), 3.06 (d, J2,3b = 6.6 Hz, 1H, H-2), 2.83
(unresolved, 1H, H-3a), 2.0 (t, J3b,3a = J3b,2 = 6.6 Hz, 1H, H-3b); 13C
NMR: d 162.1 (C-4), 112.0–157.0 (aryl C), 61.0 and 59.0 ((300,400-
O-CH3), 49.5 (C-2), 39.7 (C-3); EIMS (m/z, %): 391 [M+Å, 6].
5.2.3.6. 2-(300-Fluorophenyl)-4-(30-hydroxyphenyl)-2,3-dihydro-
1,5-benzothiazepine (32). Yield 73%; mp 73 °C; 1H NMR (DMSO-
d6): d 9.95 (s, 1H, OH), 7.90–6.59 (m, 12H, aryl H), 5.10 (dd,
J
J
2,3a = 9.9 Hz, J2,3b = 12.9 Hz, 1H, H-2), 3.27 (dd, J3a,3b = 12.9 Hz,
3a,2 = 9.9 Hz, 1H, H-3a), 2.66 (t, J3b,3a = J3b,2 = 12.9 Hz, 1H, H-3b);
13C NMR: d 162.0 (C-4), 113.0–164.7 (aryl C), 51.4 (C-2), 32.8 (C-
3); EIMS (m/z, %): 349 [M+Å, 7].
5.2.3.15. 2-(400-Hydroxy-300-methoxyphenyl)-4-(30-hydroxyphenyl)-
2,3-dihydro-1,5-benzothiazepine (41). Yield 55%; mp 108 °C; 1H
NMR (DMSO-d6): d 8.1 and 8.08 (s, 2H, OH), 7.04–8.04 (m, 11H, aryl
H), 3.83 (s, 3H,O-CH3), 3.43 (d, J2,3b = J = 14.1 Hz, 1H, H-2), 2.50
(unresolved, 1H H-3a), 1.03 (d, J3b,2 = 14.1 Hz, 1H, H-3b); 13C
NMR: d 158.3 (C-4), 113.0–157.9 (aryl C), 55.9 (O-CH3), 45.5 (C-
2), 28.2 C-3); EIMS (m/z, %): 376 [M+Å, 5].
5.2.3.7. 2-(400-Fluorophenyl)-4-(30-hydroxyphenyl)-2,3-dihydro-
1,5-benzothiazepine (33). Yield 93%; mp 79–80 °C; 1H NMR
(DMSO-d6): d 8.60 (s, 1H, OH), 7.06–8.19 (m, 12H, aryl H), 5.27
(dd, J2,3b = 12.9 Hz, J2,3a = 5.0 Hz, 1H, H-2), 3.50 (dd, J3a,3b = 12.9 Hz,
J
3a,2 = 5.0, 1H, H-3a), 2.97 (t, J3b,3a = J3b,2 = 12.9 Hz, 1H, H-3b); 13C
NMR: d 168.3 (C-4), 113.9–163.3 (aryl C), 59.5 (C-2), 37.3 (C-3);
5.2.3.16. 2-(300-Nitrophenyl)-4-(30-hydroxyphenyl)-2,3-dihydro-
1,5-benzothiazepine (42). Yield 83%; mp 82–84 °C; 1H NMR
(DMSO-d6): d 9.70 (s, 1H, OH), 6.96–8.22 (m, 12H, aryl H), 5.42
EIMS (m/z, %): 349 [M+Å, 8].
5.2.3.8. 2-(400-Bromophenyl)-4-(30-hydroxyphenyl)-2,3-dihydro-
1,5-benzothiazepine (34). Yield 82%; mp 198 °C; 1H NMR (DMSO-
d6): d 9.78 (s, 1H, OH), 7.02–7.48 (m, 12H, aryl H), 4.94 (dd,
J2,3a = 10.0 Hz, J2,3b = 12.9 Hz, 1H, H-2), 3.25 (dd, J3a,3b = 12.9 Hz,
(dd, J2,3a = J = 9.0 Hz, J2,3b = 12.6 Hz, 1H, H-2), 3.38 (dd, J 3a,3b =
12.9 Hz, J3a,2 = 9.0 Hz, 1H, H-3a), 2.86 (t, J3b,2 = J3b,3a = 12.9 Hz, 1H,
H-3b); 13C NMR: d 169.0 (C-4), 114.1–158.1 (aryl C), 58.0 (C-2),
37.0 (C-3); EIMS (m/z, %): 376 [M+Å, 7].
J
3a,2 = 10.0 Hz, 1H, H-3a), 3.14 (t, J3b,2 = J3b,3a = 12.9 Hz, 1H, H-3b);
13C NMR: d 165.0 (C-4), 118.2–158.4 (aryl C), 50.1 (C-2), 40.0 (C-
3); EIMS (m/z, %): 411 [M+Å+2, 9], 409 [M+Å, 10].
5.2.3.17. 2-(400-Nitrophenyl)-4-(30-hydroxyphenyl)-2,3-dihydro-
1,5-benzothiazepine (43). Yield 90%; mp 73 °C; 1H NMR (DMSO-