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7), 124.10 (C-4), 125.20 (C-1), 126.85 (C-30, 50), 126.96 (C-20, 60),
127.60 (C-10), 127.92 (C-40), 128.20 (C-8), 128.42 (C-300, 500), 128.60
(C-200, 600), 128.98 (C-100), 130.10 (C-400), 132.60 (C-3), 133.29 (C-4a),
135.10 (C-2),138.41 (C-5a),143.20 (C-12a),158.32 (C-4b); ESI-MS m/
z: (M)þ 438, (M þ 1)þ 439.1, (M þ 2)þ 440; Anal. Calcd. for
(C-30, 50), 126.92 (C-20, 60), 127.88 (C-10), 128.06 (C-40), 128.31 (C-300,
500), 128.50 (C-8), 128.83 (C-200, 600), 131.42 (C-100), 132.20 (C-3),
133.88 (C-4a), 135.60 (C-2), 138.50 (C-5a), 141.10 (C-400), 142.92 (C-
12a),157.25 (C-4b); ESI-MS m/z: (M)þ 452.2, (M þ 1)þ 453, (M þ 2)þ
454.2; Anal. Calcd. for C29H22ClNS (452.01): C, 77.06; H, 4.91; N,
3.10; S, 7.09. Found: C, 77.37; H, 5.22; N, 3.41; S, 7.38.
C
28H20ClNS (437.98): C, 76.78; H, 4.60; N, 3.20; S, 7.32. Found: C,
77.03; H, 4.22; N, 3.49; S, 7.58.
4.4.9. 11-(4-Methoxyphenyl)-12-phenyl-11a,12-dihydro-11H-indeno
4.4.5. 12-Phenyl-11-p-tolyl-11a,12-dihydro-11H-indeno[2,1-c][1,5]
benzothiazepine (3e)
[2,1-c][1,5]benzothiazepine (3i)
Yield 75.22%; mp 194e196 ꢃC; IR (KBr): 1601 (C¼N) cmꢁ1
;
1H
Yield 74.22%; mp 117e119 ꢃC; IR (KBr): 1604 (C¼N) cmꢁ1
;
1H
NMR (300 MHz, CDCl3):
d
3.72 (dd, 1H, J ¼ 11.7 Hz, 4.2 Hz, H-11a),
NMR (300 MHz, CDCl3):
d
2.42 (s, 3H, CH3), 3.95 (dd, 1H, J ¼ 11.7 Hz,
3.80 (s, 3H, OCH3), 3.99 (d, 1H, J ¼ 4.2 Hz, H-12), 4.32 (d, 1H,
J ¼ 11.7 Hz, H-11), 6.76 (d, 2H, J ¼ 8.4 Hz, H-300, 500), 6.88e7.01 (m,
2H, H-7, 9), 7.15e7.70 (m, 12H, H-1, 2, 3, 6, 8, 20, 30, 40, 50, 60, 200, 600),
4.2 Hz, H-11a), 4.42 (d, 1H, J ¼ 4.2 Hz, H-12), 5.02 (d, 1H, J ¼ 11.7 Hz,
H-11), 6.57e6.71 (m, 2H, H-7, 9), 6.82e7.79 (m, 14H, H-1, 2, 3, 6, 8,
20, 30, 40, 50, 60, 200, 30, 500, 600), 7.98 (dd, 1H, J ¼ 8.1 Hz, 2.1 Hz, H-4); 13C
7.92 (dd, 1H, J ¼ 8.1 Hz, 2.1 Hz, H-4); 13C NMR (CDCl3):
d 53.18 (C-
NMR (CDCl3):
d
21.05 (CH3), 53.60 (C-11a), 58.25 (C-12), 67.15 (C-
11a), 55.13 (OCH3), 57.80 (C-12), 65.80 (C-11), 113.89 (C-300, 500),
120.80 (C-9a), 121.46 (C-6), 123.28 (C-4), 123.35 (C-7), 124.20 (C-9),
125.66 (C-1), 126.30 (C-8), 126.60 (C-30, 50), 126.93 (C-20, 60), 127.47
(C-10), 128.58 (C-40), 128.89 (C-200, 600), 130.06 (C-100), 131.73 (C-3),
133.31 (C-4a), 134.37 (C-2), 137.27 (C-5a), 143.36 (C-12a), 156.50
(C-4b), 158.07 (C-4”), ESI-MS m/z: (M þ H)þ 434.4; Anal. Calcd. for
11), 119.40 (C-9a), 119.96 (C-6), 122.02 (C-7), 123.16 (C-9), 124.12 (C-
4), 125.24 (C-1), 126.60 (C-8), 126.62 (C-30, 50), 126.80 (C-20, 60),
127.56 (C-10), 127.96 (C-40), 128.35 (C-300, 500), 128.77 (C-200, 600),
130.72 (C-100), 132.40 (C-3), 133.16 (C-4a), 135.34 (C-2), 137.90 (C-
5a), 141.06 (C-400), 143.29 (C-12a), 157.12 (C-4b); ESI-MS m/z:
(M þ Na)þ 440.4; Anal. Calcd. For C29H23NS (417.56): C, 83.41; H,
5.55; N, 3.35; S, 7.68. Found: C, 83.06; H, 5.32; N, 3.63; S, 7.98.
C29H23NOS (433.56): C, 80.34; H, 5.35; N, 3.23; S, 7.40. Found: C,
80.66; H, 5.02; N, 3.52; S, 7.12.
4.4.6. 8-Methyl-12-phenyl-11-p-tolyl-11a,12-dihydro-11H-indeno
4.4.10. 11-(4-Methoxyphenyl)-8-methyl-12-phenyl-11a,12-dihydro-
[2,1-c][1,5]benzothiazepine (3f)
11H-indeno[2,1-c][1,5]benzothiazepine (3j)
Yield 76.14%; mp 125e127 ꢃC; IR (KBr): 1612 (C¼N) cmꢁ1
;
1H
Yield 79.19%; mp 202 ꢃC; IR (KBr): 1605 (C¼N) cmꢁ1
;
1H NMR
NMR (500 MHz, CDCl3):
d
2.43 (s, 3H, CH3), 2.48 (s, 3H, CH3), 3.66
(300 MHz, CDCl3):
d
2.49 (s, 3H, CH3), 3.56 (dd, 1H, J ¼ 11.7 Hz,
(dd, 1H, J ¼ 12.0 Hz, 5.0 Hz, H-11a), 3.91 (d, 1H, J ¼ 5.0 Hz, H-12),
4.69 (d,1H, J ¼ 12.0 Hz, H-11), 6.56e7.74 (m,15H, H- 1, 2, 3, 6, 7, 9, 20,
30, 40, 50, 60, 200, 300, 500, 600), 7.93 (dd, 1H, J ¼ 7.5 Hz, 2.0 Hz, H-4); 13C
4.7 Hz, H-11a), 3.83 (s, 3H, OCH3), 4.32 (d, 1H, J ¼ 4.7 Hz, H-12), 4.96
(d,1H, J ¼ 11.7 Hz, H-11), 6.87e7.71 (m,15H, H-1, 2, 3, 6, 7, 9, 20, 30, 40,
50, 60, 200, 300, 500, 600), 7.96 (dd, 1H, J ¼ 7.8 Hz, 2.1 Hz, H-4); 13C NMR
NMR (CDCl3):
d
20.75 (CH3), 21.05 (CH3), 53.80 (C-11a), 58.10 (C-12),
(CDCl3): d 21.42 (CH3 ), 53.72 (C-11a), 55.25 (OCH3), 57.80 (C-12),
67.59 (C-11), 118.60 (C-9a), 120.23 (C-9), 122.96 (C-6), 123.92 (C-4),
125.24 (C-1), 126.42 (C-7), 126.82 (C-30, 50), 127.02 (C-20, 60), 127.65
(C-10), 128.10 (C-40), 128.60 (C-300, 500), 128.92 (C-200, 600), 131.24 (C-
100), 131.88 (C-3), 133.70 (C-4a), 135.40 (C-2), 136.12 (C-8), 138.10 (C-
5a), 140.23 (C-4"), 142.73 (C-12a), 156.45 (C-4b); ESI-MS m/z:
(M þ H)þ 432.4; Anal. Calcd. for C30H25NS (431.59): C, 83.49; H,
5.84; N, 3.25; S, 7.43. Found: C, 83.15; H, 5.56; N, 3.58; S, 7.11.
65.60 (C-11), 113.98 (C-300, 500), 119.60 (C-9a), 120.51 (C-9), 123.02
(C-6), 123.60 (C-4), 124.60 (C-1), 126.19 (C-7), 126.80 (C-30, 50),
127.01 (C-20, 60),127.25 (C-200, 600),127.62 (C-10),128.65 (C-40),130.21
(C-100), 131.07 (C-3), 133.25 (C-4a), 134.65 (C-2), 135.50 (C-8), 137.92
(C-5a), 143.64 (C-12a), 156.63 (C-4b), 159.12 (C-400), ESI-MS m/z:
(M þ H)þ 448.7; Anal. Calcd. for C30H25NOS (447.59): C, 80.50; H,
5.63; N, 3.13; S, 7.16. Found: C, 80.79, H, 5.91; N, 3.41; S, 7.33.
4.4.7. 8-Methoxy-12-phenyl-11-p-tolyl-11a,12-dihydro-11H-indeno
4.4.11. 8-Methoxy-11-(4-methoxyphenyl)-12-phenyl-11a,12-dihydro-
[2,1-c][1,5]benzothiazepine (3g)
11H-indeno[2,1-c][1,5]benzothiazepine (3k)
Yield 78.24%; mp 130e132 ꢃC; IR (KBr): 1596 (C¼N) cmꢁ1
;
1H
Yield 77.26%; mp 190e191 ꢃC; IR (KBr): 1599 (C¼N) cmꢁ1
;
1H
NMR (500 MHz, CDCl3):
d
2.47 (s, 3H, CH3), 3.42 (dd, 1H, J ¼ 12.0 Hz,
NMR (300 MHz, CDCl3):
d
3.66 (dd, 1H, J ¼ 11.7 Hz, 4.5 Hz, H-11a),
5.0 Hz, H-11a), 3.81 (s, 3H, OCH3), 4.32 (d, 1H, J ¼ 5.0 Hz, H-12), 4.69
(d, 1H, J ¼ 12.0 Hz, H-11), 6.62e7.78 (m, 15H, H-1, 2, 3, 6, 7, 9, 20, 30,
40, 50, 60, 200, 300, 500, 600), 7.96 (dd, 1H, J ¼ 7.5 Hz, 2.0 Hz, H-4); 13C NMR
3.83 (s, 3H, OCH3), 3.88 (s, 3H, OCH3), 4.38 (d, 1H, J ¼ 4.5 Hz, H-12),
5.0 (d, 1H, J ¼ 11.7 Hz, H-11), 6.78e7.65 (m, 15H, H-1, 2, 3, 6, 7, 9, 20,
30, 40, 50, 60, 200, 300, 500, 600), 7.98 (dd, 1H, J ¼ 7.8 Hz, 2.1 Hz, H-4); 13C
(CDCl3):
d
21.06 (CH3), 53.90 (C-11a), 55.29 (OCH3), 58.10 (C-12),
NMR (CDCl3): d 53.40 (C-11a), 55.02 (OCH3), 55.43 (OCH3), 58.03 (C-
67.43 (C-11), 112.48 (C-7), 118.10 (C-9), 119.30 ( C-9a), 122.60 (C-6),
124.10 (C-4), 125.80 (C-1), 126.53 (C-30, 50), 126.72 (C-20, 60), 127.56
(C-10), 127.92 (C-40), 128.12 (C-300, 500), 128.40 (C-200, 600), 130.68 (C-
100), 132.12 (C-3), 133.68 (C-4a), 134.98 (C-2), 137.96 (C-5a), 140.42
(C-400), 143.75 (C-12a), 154.58 (C-8), 156.52 (C-4b); ESI-MS m/z:
(M þ H)þ 448.3; Anal. Calcd. for C30H25NOS (447.59): C, 80.50; H,
5.63; N, 3.13; S, 7.16. Found: C, 80.25; H, 5.92; N, 3.45; S, 6.91.
12), 65.92 (C-11), 112.60 (C-7), 113.98 (C-300, 500), 118.25 (C-9), 119.96
(C-9a), 121.42 (C-6), 124.17 (C-4), 125.85 (C-1), 126.76 (C-30, 50),
126.99 (C-20, 60), 127.56 (C-10), 127.83 (C-40), 129.04 (C-200, 600),
130.22 (C-100), 131.07 (C-3), 134.79 (C-4a), 135.54 (C-2), 138.25 (C-
5a), 142.85 (C-12a), 154.25 (C-8), 157.23 (C-4b), 159.40 (C-400), ESI-
MS m/z: (M þ H)þ 464.3; Anal. Calcd. for C30H25NO2S (463.59): C,
77.72; H, 5.44; N, 3.02; S, 6.92. Found: C, 77.98; H, 5.13; N, 3.36; S,
6.63.
4.4.8. 8-Chloro-12-phenyl-11-p-tolyl-11a,12-dihydro-11H-indeno
[2,1-c][1,5]benzothiazepine (3h)
4.4.12. 8-Chloro-11-(4-methoxyphenyl)-12-phenyl-11a,12-dihydro-
Yield 82.29%; mp 135e136 ꢃC; IR (KBr): 1610 (C¼N) cmꢁ1
;
1H
11H-indeno[2,1-c][1,5]benzothiazepine (3l)
NMR (300 MHz, CDCl3):
d
2.43 (s, 3H, CH3), 3.66 (dd, 1H, J ¼ 11.7 Hz,
Yield 79.98%; mp 196e198 ꢃC; IR (KBr): 1614 (C¼N) cmꢁ1
;
1H
4.2 Hz, H-11a), 3.94 (d, 1H, J ¼ 4.2 Hz, H-12), 4.56 (d, 1H, J ¼ 11.7 Hz,
NMR (300 MHz, CDCl3):
d
3.66 ( dd, 1H, J ¼ 11.7 Hz, 4.2 Hz, H-11a),
H-11), 6.60e7.73 (m, 15H, H-1, 2, 3, 6, 7, 9, 20, 30, 40, 50, 60, 200, 300, 500,
3.87 (s, 3H, OCH3), 4.40 (d, 1H, J ¼ 4.2 Hz, H-12), 4.78 (d, 1H,
J ¼ 11.7 Hz, H-11), 6.75e7.69 (m, 15H, H-1, 2, 3, 6, 7, 9, 20, 30, 40, 50, 60,
200, 300, 500, 600), 7.98 (dd,1H, J ¼ 7.8 Hz, 2.1 Hz, H-4); 13C NMR (CDCl3):
600), 7.91 (dd, 1H, J ¼ 8.1 Hz, 2.1 Hz, H-4); 13C NMR (CDCl3):
d 21.58
(CH3), 53.58 (C-11a), 57.96 (C-12), 66.12 (C-11),118.82 (C-9a),120.25
(C-6), 121.40 (C-9), 122.96 (C-7), 123.75 (C-4), 125.89 (C-1), 126.40
d
53.90 (C-11a), 55.13 (OCH3), 58.10 (C-12), 65.70 (C-11), 113.98 (C-