S. Mor, S. Nagoria, S. Sindhu, M. Khatri, G. Sidhu, and V. Singh
Vol 000
J = 7.00 Hz, OCH2CH3), 4.01 (d, 1H, J = 4.45 Hz, C12–H),
4.35 (d, 1H, J = 11.65 Hz, C11–H), 6.59 (d, 2H,
J = 8.70 Hz, C3″–H, C5″–H), 6.86–6.89 (m, 1H, Ar-H),
6.99 (d, 2H, J = 8.70 Hz, C2″–H, C6″–H), 7.11 (dd, 1H,
J = 8.25 and 1.20 Hz, Ar-H), 7.24–7.41 (m, 9H, Ar-H),
7.60 (dd, 1H, J = 7.95 and 1.15 Hz, Ar-H), 7.92–7.93
(m, 1H, Ar-H); 13C nmr (125 MHz, CDCl3): δ 14.74
(OCH2CH3), 53.15 (C11a), 57.53 (C12), 63.20
(OCH2CH3), 65.56 (C11), 113.96 (C3″, C5″), 121.05,
(OCH3), 58.10 (C12), 63.18 (OCH2CH3), 67.42 (C11),
113.95 (C3″, C5″), 115.01, 118.10, 121.15, 123.50,
0
0
126.92, 127.75, 128.60 (C2 , C6 ), 128.65, 128.81 (C2″,
0
0
C6″), 129.03 (C3 , C5 ), 130.31, 132.40, 134.21, 138.10,
142.65, 146.62, 148.71, 157.48, 157.84, 165.70 (C4b); ms
(TOF ESI) m/z: [M + H]+ calcd. for C31H27NO2S:
478.1841; found, 478.1845. Anal. Calcd. for
C31H27NO2S (477.62): C, 77.96; H, 5.70; N, 2.93.
Found: C, 77.68; H, 5.95; N, 2.75.
0
0
121.58, 126.38, 126.90, 127.56, 128.56 (C2 , C6 ),
8-Bromo-11-(4-ethoxyphenyl)-12-phenyl-11a,12-dihydro-
0
0
128.66, 128.83 (C2″, C6″), 129.01 (C3 , C5 ), 129.06,
130.24, 131.24, 132.37, 134.23, 138.03, 142.61, 146.58,
148.36, 157.47, 165.68 (C4b); ms (TOF ESI) m/z:
[M + H]+ calcd. for C30H25NOS: 448.1735; found,
448.1730. Anal. Calcd. for C30H25NOS (447.17): C,
80.50; H, 5.63; N, 3.13. Found: C, 80.43; H, 5.75; N, 3.38.
11H-indeno[2,1-c][1,5]
benzothiazepine
(5i).
This
compound was obtained as yellow solid, yield 55%; mp
196–198°C; ir (KBr): 1604 (C═N str.), 2930, 2963
(aliphatic C–H str.), 3022, 3059 (aromatic C–H
1
str.) cmꢀ1; H nmr (400 MHz, CDCl3): δ 1.31 (t, 3H,
J = 7.00 Hz, OCH2CH3), 3.70 (dd, 1H, J = 11.70 and
4.20 Hz, C11a–H), 3.83 (q, 2H, J = 7.00 Hz, OCH2CH3),
4.41 (d, 1H, J = 4.20 Hz, C12–H), 4.80 (d, 1H,
J = 11.70 Hz, C11–H), 6.57 (d, 2H, J = 8.60 Hz, C3″–H,
C5″–H), 6.97 (d, 2H, J = 8.60 Hz, C2″–H, C6″–H),
7.14–7.44 (m, 10H, Ar-H), 7.59 (d, 1H, J = 8.32 Hz,
Ar-H), 7.97–8.02 (m, 1H, Ar-H); 13C nmr (100 MHz,
CDCl3): δ 14.72 (OCH2CH3), 53.83 (C11a), 58.17 (C12),
63.19 (OCH2CH3), 66.80 (C11), 113.97 (C3″, C5″),
119.48, 121.25, 121.61, 124.13, 126.86, 127.28,
11-(4-Ethoxyphenyl)-8-methyl-12-phenyl-11a,12-dihydro-
11H-indeno[2,1-c][1,5]
benzothiazepine
(5g).
This
compound was obtained as light orange crystals, yield
58%; mp 145–148°C; ir (KBr): 1601 (C═N str.), 2887,
2930, 2980 (aliphatic C–H str.), 3080 (aromatic C–H
str.) cmꢀ1; H nmr (400 MHz, CDCl3): δ 1.34 (t, 3H,
1
J = 7.00 Hz, OCH2CH3), 2.41 (s, 3H, CH3), 3.58 (dd,
1H, J = 11.76 and 4.64 Hz, C11a–H), 3.86 (q, 2H,
J = 7.00 Hz, OCH2CH3), 4.34 (d, 1H, J = 4.64 Hz,
C12–H), 4.97 (d, 1H, J = 11.76 Hz, C11–H), 6.58 (d, 2H,
J = 8.68 Hz, C3″–H, C5″–H), 6.43–6.85 (m, 9H, Ar-H),
6.98 (d, 2H, J = 8.68 Hz, C2″–H, C6″–H), 7.58 (d, 1H,
J = 8.32 Hz, Ar-H), 7.64–7.67 (m, 1H, Ar-H), 7.90–7.94
(m, 1H, Ar-H); 13C nmr (100 MHz, CDCl3): δ 14.73
(OCH2CH3), 21.43 (CH3), 53.80 (C11a), 57.95 (C12),
63.21 (OCH2CH3), 66.92 (C11), 113.94 (C3″, C5″),
0
0
128.59 (C2 , C6 ), 128.62, 128.82 (C2″, C6″), 128.99
0
0
(C3 , C5 ), 129.23, 130.32, 132.48, 134.39, 137.98,
142.61, 146.55, 148.52, 157.49, 165.91 (C4b); ms
(TOF ESI) m/z: [M + H]+ calcd. for C30H24BrNOS:
526.0840 (79Br), 528.0820 (81Br); found, 526.0835
(79Br),
528.0816
(81Br).
Anal.
Calcd.
for
C30H24BrNOS (526.49): C, 68.44; H, 4.59; N, 2.66.
0
121.48, 122.87, 126.84, 127.14, 128.15, 128.62 (C2 ,
Found: C, 68.57; H, 4.33; N, 2.51.
0
0
0
C6 ), 128.81 (C2″, C6″), 129.01 (C3 , C5 ), 130.42, 132.45,
132.45, 134.38, 135.50, 138.24, 142.58, 146.60, 148.55,
157.51, 165.75 (C4b); ms (TOF ESI) m/z: [M + H]+
calcd. for C31H27NOS: 462.1892; found, 462.1887. Anal.
Calcd. for C31H27NOS (461.62): C, 80.66; H, 5.90; N,
3.03. Found: C, 80.83; H, 5.75; N, 3.27.
8-Chloro-11-(4-ethoxyphenyl)-12-phenyl-11a,12-dihydro-
11H-indeno[2,1-c][1,5]
benzothiazepine
(5j).
This
compound was obtained as yellow solid, yield 53%; mp
124–128°C; ir (KBr): 1605 (C═N str.), 2876, 2918, 2963
(aliphatic C–H str.), 3024, 3063 (aromatic C–H
1
str.) cmꢀ1; H nmr (400 MHz, CDCl3): δ 1.32 (t, 3H,
J = 7.00 Hz, OCH2CH3), 3.69 (dd, 1H, J = 11.70 and
4.40 Hz, C11a–H), 3.84 (q, 2H, J = 7.00 Hz, OCH2CH3),
4.42 (d, 1H, J = 4.40 Hz, C12–H), 4.79 (d, 1H,
J = 11.68 Hz, C11–H), 6.59 (d, 2H, J = 8.56 Hz, C3″–H,
C5″–H), 6.96 (d, 2H, J = 8.56 Hz, C2″–H, C6″–H),
7.21–7.43 (m, 10H, Ar-H), 7.60 (d, 1H, J = 8.20 Hz,
Ar-H), 7.96–8.01 (m, 1H, Ar-H); 13C nmr (100 MHz,
CDCl3): δ 14.73 (OCH2CH3), 53.87 (C11a), 58.15 (C12),
63.21 (OCH2CH3), 66.83 (C11), 113.92 (C3″, C5″),
120.35, 121.63, 124.53, 126.51, 126.88, 127.31, 128.58
11-(4-Ethoxyphenyl)-8-methoxy-12-phenyl-11a,12-dihydro-
11H-indeno[2,1-c][1,5]
benzothiazepine
(5h).
This
compound was obtained as yellow crystals, yield 52%;
mp 156–160°C; ir (KBr): 1603 (C═N str.), 2887, 2966
(aliphatic C–H str.), 3019, 3073 (aromatic C–H
1
str.) cmꢀ1; H nmr (400 MHz, CDCl3): δ 1.33 (t, 3H,
J = 7.00 Hz, OCH2CH3), 3.64 (dd, 1H, J = 11.68 and
4.40 Hz, C11a–H), 3.68 (s, 3H, OCH3), 3.85 (q, 2H,
J = 7.00 Hz, OCH2CH3), 4.39 (d, 1H, J = 4.40 Hz,
C12–H), 5.02 (d, 1H, J = 11.68 Hz, C11–H), 6.60 (d, 2H,
J = 8.60 Hz, C3″–H, C5″–H), 6.65 (d, 1H, J = 2.60 Hz,
Ar-H), 6.98 (d, 2H, J = 8.60 Hz, C2″–H, C6″–H),
7.13–7.43 (m, 9H, Ar-H), 7.58 (d, 1H, J = 7.95 Hz,
Ar-H), 7.92–7.93 (m, 1H, Ar-H); 13C nmr (100 MHz,
CDCl3): δ 14.75 (OCH2CH3), 53.68 (C11a), 55.42
0
0
0
0
(C2 , C6 ), 128.63, 128.85 (C2″, C6″), 128.99 (C3 , C5 ),
130.21, 130.37, 132.47, 134.35, 138.29, 142.63, 146.54,
148.54, 157.50, 165.89 (C4b); ms (TOF ESI) m/z:
[M + H]+ calcd. for C30H24ClNOS: 482.1345 (35Cl),
484.1316 (37Cl); found, 482.1342 (35Cl), 484.1313
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet