146
H. Loghmani-Khouzani, P. Tamjidi, I. Mohammadpoor-Baltork, M. Yaeghoobi, N. Abd.Rahman,
Vol 51
A. R. Khosropour, M. Moghadam, S. Tangestaninejad, V. Mirkhani, et al.
(10.92), 253.96 (37.14), 240.98 (100.00), 225.96 (85.71), 197.97
(84.08), 196.95 (73.88), 137.95 (61.22), 108.95 (33.88), 102.99
(67.76), 77.02 (65.71); Anal. Calcd for C22H18NSOCl: C, 69.55; H,
4.78; N, 3.96; S, 8.44. Found: C, 68.98; H, 4.77; N, 3.67; S, 8.15.
2-(4-Fluorophenyl)-4-(4-methylphenyl)-2,3-dihydro-1,5-
benzothiazepine (5). White crystals; mp 131–133ꢀC; IR (KBr)
n: 3026, 2891, 1602, 1505, 1451, 1321, 1321, 1220, 1155, 819,
744 cmÀ1;1H NMR (400 MHz, CDCl3): d 2.45 (s, 3H, CH3), 3.01
(t, 1H, J = 12.8Hz, CH2), 3.28 (dd, 1H, J1 = 13.0 Hz, J2 = 4.6 Hz,
CH2), 4.97 (dd, 1H, J1 = 12.2 Hz, J2 = 4.6 Hz, CH), 7.00 (t, 2H,
J = 8.4 Hz), 7.15 (t, 1H, J = 7.2 Hz), 7.30 (d, 5H, J = 7.6 Hz), 7.48
(t, 1H, J = 8.0 Hz), 7.60 (d, 1H, J = 7.6 Hz), 7.95 (d, 2H,
4.98 (dd, 1H, J1 = 24.4Hz, J2 = 9.6 Hz, CH), 6.93 (t, 1H,
J= 7.2 Hz), 7.09 (d, 1H, J= 7.2 Hz), 7.22 (d, 2H, J=8.4Hz), 7.33
(d, 1H, J = 8.4 Hz), 7.46 (d, 4H, J= 6.4 Hz), 7.57 (d, 1H,
J= 6.8 Hz), 7.63 (d, 1H, J= 7.2 Hz), 14.5 (s, 1H, OH); 13C NMR
(100 MHz, CDCl3): 36.62 (CH2), 59.27 (CH), 118.65, 118.75,
121.82, 123.95, 125.73, 126.51, 127.79, 128.28, 130.18, 132.00,
133.77, 135.18, 142.69, 162.77 (Ar C), 172.83 (C═N); MS
(EI, 70 eV) m/z (%): 410.96 (4.27) [M + 2]+, 408.97 (4.11) [M+],
240.02 (4.16), 227.00 (100.00), 198.96 (40.41), 197.95 (30.85),
181.85 (7.35), 108.89 (16.90), 102.89 (20.84), 90.89 (16.65), 76.89
(50.38), 64.91 (32.43); Anal. Calcd for C21H16NSOBr: C, 61.47;
H, 3.93; N, 3.41; S, 7.81. Found: C, 60.95; H, 4.37; N, 3.96; S, 7.48.
4-(2-Hydroxyphenyl)-2-(4-methylphenyl)-2,3-dihydro-1,5-
benzothiazepine (10). Light yellow crystals; mp 156–158ꢀC
(Lit [28] 155–157ꢀC); IR (KBr) n: 3434, 3049, 2980, 1596, 1448,
J = 7.6 Hz) cmÀ1 13C NMR (100MHz, CDCl3): d 21.50 (CH3),
;
37.68 (CH2), 59.71 (CH), 122.57, 125.19, 125.40, 127.42,
127.69, 127.77, 129.53, 129.85, 134.88, 135.00, 140.12, 141.63,
152.57, 163.38 (Ar C), 168.61 (C═N); MS (EI, 70 eV) m/z (%):
374.05 (4.17) [M+], 256.09 (2.66), 238.10 (2.91), 225.10
(100.00), 210.06 (3.05), 197.04 (2.29), 122.08 (6.08), 91.12
(15.77), Anal. Calcd for C22H18FNS: C, 76.05; H, 5.22; N, 4.02;
S, 9.23; Found: C, 75.85; H, 5.38; N, 3.87; S, 9.01.
1
1256, 1207, 810, 745, 498 cmÀ1; H NMR (400MHz, CDCl3): d
2.37 (s, 3H, CH3), 3.11 (t, 1H, J =12.8Hz, CH2), 3.43 (d, 1H,
J = 12.8Hz, CH2), 5.06 (d, 1H, J = 12Hz, CH), 6.94 (t, 1H,
J = 8.0 Hz), 7.4 (s, 1H),7.15 (d, 2H, J =8.0 Hz), 7.22 (d, 3H,
J = 8.0 Hz), 7.35 ( d, 1H, J = 8.0 Hz), 7.42 (t, 1H, J = 8.0Hz), 7.52
(t, 1H, J = 8.0 Hz), 7.36 (q, 2H, J = 8.0 Hz), 14.35 (S, 1H, OH);
MS (EI, 70 eV) m/z (%): 345.09 (2.97) [M+], 240.06 (2.97),
227.03 (100.00), 199.05 (31.91), 198.05 (19.68), 118.04 (12.41),
108.97 (10.37).
2-(4-Chlorophenyl)-4-(4-chlorophenyl)-2,3-dihydro-1,5-
benzothiazepine (6). White crystals; mp 124–126ꢀC; IR (KBr)
n: 3052, 2883, 1607, 1562, 1486, 1398, 1319, 1088, 1010, 806,
; d 3.02 (t, 1H,
757 cmÀ1 1H NMR (400MHz, CDCl3):
J = 12.8Hz, CH2), 3.24 (dd, 1H, J1 = 13.2 Hz, J2 = 4.8 Hz, CH2),
4.94 (dd, 1H, J1 = 12.2 Hz, J2 = 5.0 Hz, CH), 7.17 (t, 1H,
J = 7.6 Hz), 7.23–7.31 (m, 6H), 7.46–7.51 (m, 2H), 7.60 (d, 1H,
J = 7.6 Hz), 7.99 (d, 1H, J = 8.4 Hz); 13C NMR (100 MHz,
CDCl3): 37.33 (CH2), 59.72 (CH), 122.37, 125.43, 125.60,
127.46, 128.75, 128.97, 129.04, 129.33, 130.05, 133.59, 135.09,
135.99, 137.43, 142.31, 152.21 (Ar C), 167.52 (C═N); MS
(EI, 70 eV) m/z (%): 384.88 (2.19) [M+ 2]+, 382.88 (3.03) [M+],
271.94 (3.89), 248.93 (5.52), 246.94 (84.68), 244.94 (100.00),
209.99 (19.5), 137.98 (27.94), 108.97 (17.57), 107.96 (85.37),
68.98 (47.68); Anal. Calcd for C21H15Cl2NS: C, 65.63; H, 3.93;
N, 3.64; S, 8.34. Found: C, 65.24; H, 3.52; N, 3.61; S, 7.89.
4-(4-Chlorophenyl)-2-(4-(N,N-dimethylamino)phenyl)-2,3-
dihydro-1,5-benzothiazepine (7). White crystals; mp 155–157ꢀC;
IR (KBr) n: 3056, 2868, 1621, 1475, 1416, 1322, 1237, 1078,
2-(4-Fluorophenyl)-4-(2-hydroxyphenyl)-2,3-dihydro-1,5-
benzothiazepine (11). Light yellow crystals; mp 161–163ꢀC; IR
(KBr) n: 3431, 3054, 1598, 1505,1448, 1214, 1155, 823,
; d 3.08 (t, 1H,
746 cmÀ1 1H NMR (400 MHz, CDCl3):
J = 12.4Hz, CH2), 3.44 (d, 1H, J = 12 Hz, CH2), 5.09 (d, 1H,
J = 10.8Hz, CH), 6.94 (t, 1H, J = 7.2Hz), 7.04 (t, 2H, J = 8.0 Hz),
7.18 (t, 1H, J = 8.0 Hz), 7.30–7.38 (m, 3H), 7.45 (dd, 2H,
J1 = 32Hz, J2 = 7.2Hz), 7.60 (d, 2H, J = 11.2 Hz), 7.75 (d, 1H,
J = 12.8 Hz), 14.5 (s, 1H, OH); 13C NMR (125 MHz, CDCl3):
37.02 (CH2), 59.31 (CH), 115.65, 115.82, 118.62, 118.75, 125.73,
126.47, 127.77, 127.84, 128.35, 130.09, 133.72, 135.17, 139.53,
148.87, 161.35, 162.82, 163.32 (Ar C), 172.93 (C═N); MS (EI,
100 eV) m/z (%): 348.96 (56.54) [M+], 331.94 (6.45), 255.99
(10.43), 239.98 (13.09), 227.00 (100.00), 199.00 (84.29), 197.99
(76.44), 122.00 (47.64), 108.98 (43.98); Anal. Calcd for
C21H16NSOF: C, 72.18; H, 4.62; N, 4.51; S, 9.18. Found: C,
71.72; H, 5.19; N, 4.21; S, 8.71.
841, 755cmÀ1 1H NMR (400 MHz, CDCl3): d 3.05 (t, 1H,
;
J = 12.6 Hz, CH2), 3.31 (dd, 1H, J1 = 13.0Hz, J2 = 4.6Hz, CH2),
3.91 (s, 6H, CH3), 5.01 (dd, 1H, J1 = 12.6 Hz, J2 = 4.2 Hz, CH),
7.02 (d, 2H, J = 8.4 Hz), 7.16 (t, 1H, J = 7.4Hz), 7.32 (d, 1H,
J = 8.0Hz), 7.47–7.52 (m, 3H), 7.58 (d, 1H, J = 8.0 Hz), 8.02
(d, 2H, J = 8.8 Hz), 8.19 (d, 2H, J = 8.8Hz); 13C NMR (100 MHz,
CDCl3): 36.69 (CH2), 55.51 (CH3), 59.24 (CH), 76.72, 114.20,
121.66, 124.18, 125.27, 125.52, 127.04, 129.13, 129.91, 130.32,
134.98, 147.30, 150.89, 152.74, 162.32 (Ar C), 167.52 (C═N).
4-(4-Chlorophenyl)-2-(4-methoxyphenyl)-2,3-dihydro-1,5-
benzothiazepine (8). White crystals; mp 132–134ꢀC (Lit. [28]
133–135ꢀC); IR (KBr) n: 3000, 2895, 1605, 1509, 1451, 1243,
4-(2-Hydroxyphenyl)-2-phenyl-2,3-dihydro-1,5-benzothiazepine
(12). Light yellow crystals; mp 145–147ꢀC (Lit. [18] 146–147ꢀC);
IR (KBr) n: 3325, 2836, 1592, 1467, 1350, 1294, 889, 749cmÀ1
;
1H NMR (500 MHz, CDCl3): d 3.10 (t, 1H, J = 12.9Hz, CH2),
3.42 (dd, 1H, J1 = 13.3 Hz, J2 =4.4 Hz, CH2), 5.07 (dd, 1H,
J1 = 12.4Hz, J2 =4.4 Hz, CH), 6.92 (t, 1H, J = 7.6 Hz), 7.08
(d, 1H, J = 8.3 Hz), 7.25 (t, 1H, J = 7.5Hz), 7.29–7.34 (m, 5H),
7.43 (t, 1H, J = 7.7 Hz), 7.51 (t, 1H, J = 7.6Hz), 7.60 (d, 1H,
J = 8.0 Hz), 7.67 (d, 1H, J = 7.7 Hz), 14.51 (s, 1H, OH); MS
(EI, 70eV) m/z (%): 331.04 (79.08) [M+], 314.05 (8.79), 254.10
(3.79), 238.11 (4.58), 227.10 (100.00), 199.11 (90.38), 198.11
(61.09), 173.09 (30.13), 167.14 (33.89), 109.11 (61.51), 91.15
(25.21), 77.14 (32.64), 65.14 (49.37), 51.12 (35.98).
1
1088, 1007, 826, 755 cmÀ1; H NMR (400 MHz, CDCl3): d 3.05
(t, 1H, J= 12.6 Hz, CH2), 3.22 (dd, 1H, J1 = 13.2 Hz, J2 =4.8Hz,
CH2), 3.81 (s, 3H, CH3), 4.97 (dd, 1H, J1 = 12.6 Hz, J2 =4.6Hz,
CH), 6.84 (d, 2H, J= 8.8 Hz), 7.16 (t, 1H, J= 8.0 Hz), 7.23 (d, 2H,
J= 8.8 Hz), 7.29 (d, 1H, J= 7.27 Hz), 7.46 (d, 2H, J= 8.4 Hz), 7.48
(t, 2H, J= 8.0 Hz), 7.61 (d, 1H, J=8.0Hz), 7.99 (d, 2H, J=8.0Hz).
2-(4-Bromophenyl)-4-(2-hydroxyphenyl)-2,3-dihydro-1,5-
benzothiazepine (9). Yellowish needles; mp 174–176ꢀC; IR (KBr)
n: 3439, 3055, 2901, 1598, 1564, 1483,1448, 1253, 1009, 809,
4-(2-Hydroxyphenyl)-2-(4-methoxyphenyl)-2,3-dihydro-1,5-
benzothiazepine (13). Light yellow crystals; mp 160–162ꢀC
(Lit. [18] 160–161ꢀC); IR (KBr) n: 3008, 2958, 1597, 1555, 1511,
1
1251, 1030, 827, 757 cmÀ1; H NMR (400 MHz, CDCl3): d 3.09
(t, 1H, J = 12.8Hz, CH2), 3.42 (d, 1H, J = 11.2 Hz, CH2), 3.82
(s, 1H, CH3), 5.08 (d, 1H, J = 10.8Hz, CH), 6.87 (d, 2H,
J = 8.0 Hz), 6.93 (t, 1H, J = 7.2 Hz), 7.14 (d, 1H, J = 8.0 Hz), 7.25
(t, 2H, J = 8.0 Hz), 7.35 (t, 2H, J = 8.0 Hz), 7.44 (t, 1H, J =8.0 Hz),
;
748, 499cmÀ1 1H NMR (400 MHz, CDCl3): d 3.05 (t, 1H,
J = 12.6 Hz, CH2), 3.35 (dd, 1H, J1 = 19.2 Hz, J2 =10.6Hz, CH2),
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet