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7.5 Hz, 2H), 7.97 (d, J ¼ 8.5 Hz, 1H), 8.04 (s, 1H); 13C NMR (125
2-(4-(Triuromethyl)phenyl)benzo[b]thiophene-3-carbonitrile
(3k). White solid; yield: 203 mg (67%); MP 216–218 ꢀC; Rf ¼ 0.46
(hexane–EtOAc, 9 : 1); IR (KBr): 2217, 2231, 3070, 1608, 1589,
1484, 1318, 1176, 1231, 1197, 1064, 943, 878, 744, 614; 1H NMR
(500 MHz, CDCl3): d ¼ 7.85 (d, J ¼ 8.0 Hz, 1H), 7.82–7.80 (m, 3H),
7.67 (d, J ¼ 8.5 Hz, 2H), 7.63 (s, 1H), 7.40–7.34 (m, 1H); 13C NMR
MHz, CDCl3): d ¼ 114.9, 120.06, 120.09, 123.10, 123.41 (q, JC–F
¼
38.7 Hz, 1C), 123.48, 123.7, 125.2, 128.31, 128.34, 130.4, 137.1,
141.8, 142.6, 158.6; MS: m/z ¼ 317 [M]+; anal. cald for C17H10F3NS:
C, 64.34; H, 3.18; N, 4.41. Found: C, 64.37; H, 3.25; N, 4.46.
2-(3,4,5-Trimethoxyphenyl)benzo[b]thiophene]-3-carbonitrile
(3f). White solid; yield: 231 mg (65%); MP 209–210 ꢀC; Rf ¼ 0.42
(hexane–EtOAc, 9 : 1); IR (KBr): 3095, 2220, 1609, 1528, 1457,
(125 MHz, CDCl3): d ¼ 114.0, 121.9, 122.9, 123.9, 124.9 (q, JC–F
¼
103.2 Hz, 1C), 125.1, 125.8, 126.0, 129.8, 130.1, 137.7, 139.8,
140.4, 142.3; MS: m/z ¼ 303 [M]+; anal. cald for C16H8F3NS: C,
63.36; H, 2.66; N, 4.62. Found: C, 63.33; H, 2.63; N, 4.66.
2,6-Bibenzo[b]thiophene]-3-carbonitrile (3l). White solid;
yield: 209 mg (72%); MP 153–155 ꢀC; Rf ¼ 0.54 (hexane–EtOAc,
9 : 1); IR (KBr): 3082, 2215, 1531, 1456, 1318, 1256, 1056, 901,
1
1320, 1208, 1129, 1064, 937, 857, 782, 702, 627 cmꢂ1; H NMR
(500 MHz, CDCl3): d ¼ 3.79–3.82 (m, 3H), 3.84–3.92 (m, 6H),
7.04 (s, 2H), 7.33–7.37 (m, 1H), 7.41–7.45 (m, 1H), 7.72–7.75 (m,
1H), 7.84–7.87 (m, 1H); 13C NMR (100 MHz, CDCl3): d ¼ 56.2,
60.8, 61.0, 101.6, 105.5, 115.3, 122.1, 122.3, 122.59, 125.91,
126.2, 126.7, 137.0, 139.1, 140.1, 153.6, 155.0; MS: m/z ¼ 326 [M
+ H]+; anal. cald for C18H15NO3S: C, 66.44; H, 4.65; N, 4.30;
found: C, 66.47; H, 4.72; N, 4.35.
1
876, 751, 628 cmꢂ1; H NMR (500 MHz, CDCl3): d ¼ 7.46–7.52
(m, 3H), 7.53–7.60 (m, 1H), 7.92 (d, J ¼ 8.0 Hz, 2H), 7.95–7.97
(m, 2H), 8.04–8.15 (m, 1H), 8.14–8.16 (m, 1H); 13C NMR (125
MHz, CDCl3): d ¼ 114.7, 122.6, 122.8, 123.0, 125.1, 125.3, 126.2,
126.9, 129.35, 129.3, 136.6, 137.8, 138.2, 138.2, 140.4, 148.2; MS:
m/z ¼ 292 [M + H]+; anal. cald for C17H9NS2: C, 70.07; H, 3.11; N,
4.81. Found: C, 70.04; H, 3.18; N, 4.86.
2-(4-Chlorophenyl)benzo[b]thiophene-3-carbonitrile
(3g).
White solid; yield: 234 mg (78%); MP 191–193 ꢀC; Rf ¼ 0.59
(hexane–EtOAc, 9 : 1); IR (KBr): 2217, 1608, 1589, 1484, 1318,
1
1231, 1197, 1064, 943, 878, 744, 614 cmꢂ1; H NMR (400 MHz
CDCl3): d ¼ 7.46–7.57 (m, 4H), 7.82–7.87 (m, 3H), 7.97–7.99 (m,
1H); 13C NMR (125 MHz, CDCl3): d ¼ 102.5, 114.9, 122.4, 122.7,
126.3, 126.4, 129.5, 129.7, 130.0, 136.7, 137.4, 139.1, 153.5; MS:
m/z ¼ 270 [M + H]+; anal. cald for C15H8ClNS: C, 66.79; H, 2.99;
N, 5.19. Found: C, 66.74; H, 2.93; N, 5.16.
2-(Thiophenyl-2-yl)-6-(triuoromethyl)benzo[b]thiophene-3-
carbonitrile (3m). White solid; yield: 219 mg (71%); MP 147–148
ꢀC; Rf ¼ 0.57 (hexane–EtOAc, 9 : 1); IR (KBr): 2217, 1602, 1533,
1531, 1497, 1459, 1279, 1119, 1082, 948, 849, 787, 629 cmꢂ1
;
1H NMR (400 MHz, CDCl3): d ¼ 7.20–7.22 (m, 1H), 7.59, (dd, J ¼
7.5, 5.0 Hz, 1H), 7.73–7.75 (m, 1H), 7.84 (dd, J ¼ 6.3, 5.0 Hz, 1H),
8.02 (d, J ¼ 10.5 Hz, 1H), 8.08 (t, J ¼ 0.5 Hz, 1H); 13C NMR (100
MHz, CDCl3): d ¼ 114.4, 119.6, 122.5, 122.8 (q, JC–F ¼ 36.1 Hz,
1C), 123.1, 123.4, 128.3, 128.6, 129.4, 129.9, 132.8, 136.2, 141.2,
150.6; MS: m/z ¼ 309 [M]+; anal. cald for C14H6F3NS2: C, 54.36;
H, 1.96; N, 4.53.
2-(4-Chlorophenyl)-6-(triuromethyl)benzo[b]thiophene-3-
carbonitrile (3h). White solid; yield: 205 mg (61%); MP 212–214
ꢀC; Rf ¼ 0.58 (hexane–EtOAc, 9 : 1); IR (KBr): 2919, 2210, 1601,
1525, 1421, 1395, 1229, 1060, 938, 837, 744, 615 cmꢂ1; 1H NMR
(400 MHz CDCl3): d ¼ 7.52–7.55 (m, 2H), 7.76–7.79 (m, 1H),
7.83–7.87 (m, 2H), 8.09 (d, J ¼ 10.5 Hz, 1H), 8.15 (d, J ¼ 4.0 Hz,
1H); 13C NMR (100 MHz, CDCl3): d ¼ 102.4, 114.4, 120.1, 122.6,
122.9, 123.6 (q, JC–F ¼ 40 Hz, 1C), 124.0, 128.6, 128.9, 129.4,
137.1137.6, 141.5, 156.6; MS: m/z ¼ 337 [M]+; anal. cald for
2-(Thiophen-2-yl)benzo[b]thiophene-3-carbonitrile (3n). Pale
yellow solid; yield: 206 mg (76%); MP 152–154 ꢀC; Rf ¼ 0.50
(hexane–EtOAc, 9 : 1); IR (KBr): 2217, 1606, 1533, 1497, 1459,
1
1279, 1119, 1082, 948, 849, 787, 629 cmꢂ1; H NMR (500 MHz,
C
16H7ClF3NS: C, 56.90; H, 2.09; N, 4.15. Found: C, 56.95; H,
2.15; N, 4.18.
CDCl3): d ¼ 7.17–7.19 (m, 1H), 7.45 (t, J ¼ 9.5 Hz, 1H), 7.53 (t, J ¼
7.0 Hz, 2H), 7.80 (t, J ¼ 10.5 Hz, 2H), 7.92 (d, J ¼ 10 Hz, 1H); 13
C
2-(4-Flurophenyl)-6-(triuromethyl)benzo[b]thiophene-3-
carbonitrile (3i). White solid; yield 240 mg (75%); MP 216–218
ꢀC; Rf ¼ 0.40 (hexane–EtOAc, 9 : 1); IR (KBr): 2962, 2215, 1602,
1531, 1460, 1318, 1260, 1162, 1027, 934, 852, 723, 646 cmꢂ1; 1H
NMR (400 MHz, CDCl3): d ¼ 7.20 (t, J ¼ 10.5 Hz, 2H), 7.07 (d, J ¼
10.5 Hz, 1H), 7.81–7.85 (m, 2H), 8.00 (d, J ¼ 9.8 Hz, 1H), 8.07 (s,
1H); 13C NMR (100 MHz, CDCl3): d ¼ 114.3, 119.8, 122.5, 123.1,
123.7 (q, JC–F ¼ 60 Hz, 1C), 124.3, 127.0, 128.7, 129.8, 130.4,
141.4, 156.7, 163.0, 164.5 (d, JC–F ¼ 150 Hz, 1C); MS: m/z ¼ 321
[M]+; anal. cald for C16H7F4NS: C, 59.81; H, 2.20; N, 4.36. Found:
C, 59.85; H, 2.25; N, 4.38.
NMR (100 MHz, CDCl3): d ¼ 115.0, 122.1, 122.4, 126.2, 128.4,
128.6, 128.63, 128.8, 128.9, 133.5, 136.6, 138.8, 147.6; MS: m/z ¼
242 [M + H]+; anal. cald for C13H7NS2: C, 64.70; H, 2.92; N, 5.80;
found: C, 64.79; H, 2.96; N, 5.88.
6-Triuromethyl-[2,6-bibenzo[b]thiophene]-3-carbonitirle (3o).
White solid; yield: 248 mg (69%); MP 159–160 ꢀC; Rf ¼ 0.44
(hexane–EtOAc, 9 : 1); IR (KBr): 2915, 2848, 2214, 1537, 1459,
1363, 1232, 1191, 1057, 898, 754 cmꢂ1; 1H NMR (400 MHz CDCl3)
d ¼ 7.46–7.54 (m, 2H), 7.79–7.88 (m, 1H), 7.95–7.97 (m, 1H), 8.10–
8.14 (m, 3H), 8.19 (m, 1H); 13C NMR (100 MHz, CDCl3): d ¼ 114.2,
119.9, 122.1, 122.5 (q, JC–F ¼ 45.5 Hz, 1C), 122.6, 123.0, 125.2,
126.3, 128.3, 128.7, 130.23, 130.24, 136.3, 137.4, 140.5, 151.2; MS:
m/z ¼ 359 [M]+; anal. cald for C18H8F3NS2: C, 60.16; H, 2.24; N,
3.90.
2-4-Flurophenylbenzo[b]thiophene-3-carbonitrile (3j). White
solid; yield: 167 mg (66%); MP 161–163 C; Rf ¼ 0.57 (hexane–
ꢀ
EtOAc, 9 : 1); IR (KBr): 2282, 2215, 1460, 1436, 1318, 1260, 1162,
1027, 934, 852, 723, 646 cmꢂ1; 1H NMR (500 MHz, CDCl3): d ¼
7.81 (d, J ¼ 7.5 Hz, 1H), 7.76 (d, J ¼ 8.0 Hz, 1H), 7.68–7.65 (m,
1H), 7.46 (s, 1H), 7.35–7.31 (m, 2H), 7.13–7.10 (m, 2H); 13C NMR
(125 MHz, CDCl3): d ¼ 115.8, 116.0, 119.4, 122.2, 123.5, 124.3,
128.1, 128.2, 130.56, 140.6, 143.0, 161.7, 162.0 (d, JC–F ¼ 238 Hz
1C); MS: m/z ¼ 254 [M + H]+; anal. cald for C15H8FNS: C, 71.13;
H, 3.18; N, 5.53.
2-(4-Hydrxoyphenyl)benzo[b]thiophene-3-carbonitrile (3p).
White solid; yield: 158 mg (63%); MP 203 ꢀC; Rf ¼ 0.49 (hexane–
EtOAc, 9 : 1) IR (KBr): 2217, 3070, 3650, 1608, 1589, 1484, 1318,
1
1231, 1197, 1064, 943, 878, 744, 614 cmꢂ1; H NMR (400 MHz,
CDCl3) d ¼ 6.99–7.50 (m. 2H), 7.50–7.52 (m, 1H), 7.54–7.61 (m,
29944 | RSC Adv., 2015, 5, 29939–29946
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