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M. A. E. Pinto-Bazurco Mendieta et al.
Arch. Pharm. Chem. Life Sci. 2008, 341, 597–609
7.5 Hz, 1H), 7.79 (s, 1H), 8.25 (dd, J = 1.7 Hz, J = 8.6 Hz, 1H), 8.94
(dd, J = 1.7 Hz, J = 4.1 Hz, 1H);dC (CDCl3, 125 MHz) 11.4, 28.2, 55.4,
57.0, 114.0, 118.0, 121.2, 125.3, 126.8, 127.0, 128.9, 131.0, 131.4,
134.7, 137.1, 137.8, 140.3, 145.7, 149.4, 159.3; (ESI): m/z = 344 [M+
+ H].
7.55–7.60 (m, 4H), 7.66 (d, J = 8.4 Hz, 1H), 7.76 (s, 1H); dC (CDCl3,
125 MHz) 50.5 (CH2), 119.7, 123.8, 127.7, 127.9, 129.9, 135.5,
137.4, 141.7,145.7; MS (ESI): m/z = 275 [M+ + H].
1-(4-(Benzo[b]thiophen-5-yl)benzyl)-1H-imidazole 15
Synthesized according to method A1 using 15a (0.7 g,
2.91 mmol) and CDI (2.36 g, 14.6 mmol); yield: 0.18 g (21%);
white solid: m.p. 164–1658C; Rf = 0.25 (DCM / MeOH, 20 : 1); IR
(ATR) m (cm– 1) 1434 (w), 908 (m), 807 (m), 759 (m), 708 (m), 663
(m); dH (CDCl3, 500 MHz) 5.18 (s, 2H, CH2), 6.95 (s, 1H), 7.12 (s, 1H),
7.25 (d, J = 8.1 Hz, 2H), 7.38 (d, J = 5.4 Hz, 1H), 7.49 (d, J = 5.4 Hz,
1H), 7.55 (d, J = 8.4 Hz, 1H), 7.59 (s, 1H), 7.64 (d, J = 8.3 Hz, 2H),
7.93 (d, J = 8.4 Hz, 1H), 8.00 (s, 1H); dC (CDCl3, 125 MHz) 50.5 (CH2),
119.3, 121.93, 122.83, 123.7, 124.1, 127.3, 127.9, 129.9, 135.0,
139.1, 140.2, 141.4; MS (ESI): m/z = 291 [M+ + H].
8-(1-(1H-Imidazol-1-yl)propyl)-2-ethyl-5-(4-
methoxyphenyl)quinoline 10
Synthesized according to method A1 using 10a (0.40 g,
1.25 mmol) and CDI (1.61 g, 9.96 mmol); yield: 0.27 g (59%);
white solid: m.p. 1578C; Rf = 0.56 (DCM / MeOH, 95 : 5); IR (ATR) m
(cm– 1) 2969 (w), 1609 (s), 1576 (w), 1517 (s), 1498 (w), 1460 (w),
1285 (w), 1247 (s), 1177 (m), 1110 (w), 1072 (w), 1032 (m), 825 (w),
738 (m), 664 (m); dH (CDCl3, 500 MHz) 1.08 (t, J = 7.3 Hz, 3H), 1.47
(t, J = 7.6 Hz, 3H), 2.37-2.51 (m, 2H), 3.06 (q, J = 7.6 Hz, J = 15.1 Hz,
2H), 3.91 (s, 3H), 6.69 (m, 1H), 7.05 (d, J = 8.7 Hz, 2H), 7.14 (s, 1H),
7.27 (d, J = 3.8 Hz, 1H), 7.35–7.39 (m, 3H), 7.55 (d, J = 7.5 Hz, 1H),
7.82 (s, 1H), 8.15 (d, J = 8.7 Hz, 1H); dC (CDCl3, 125 MHz) 11.4, 13.2,
28.0, 31.9, 55.4, 57.1, 113.9, 117.9, 121.1, 125.1, 125.3, 125.8,
128.8, 131.0, 131.7, 134.7, 137.1, 137.2, 140.0, 145.2, 159.2,
162.6; (ESI): m/z = 372 [M+ + H].
5-(4-(1H-Imidazol-1-ylmethyl)phenyl)-1H-indole 16
Synthesized according to method A1 using 16a (0.80 g,
3.58 mmol) and CDI (3.55 g, 21.88 mmol); yield: 0.24 g (25%);
white solid: m.p. 217–2188C; Rf = 0.16 (DCM / MeOH, 20 : 1); IR
(ATR) m (cm– 1) 1509 (m), 1232 (m), 1099 (m), 1072 (m), 915 (m),
883 (m), 801 (m), 732 (s), 662 (m), 619 (m), 574 (s), 528 (m); dH
(CDCl3, 500 MHz) 5.16 (s, 2H, CH2), 6.61–6.63 (m, 1H), 6.97 (s, 1H),
7.13 (s, 1H), 7.22 (d, J = 8.4 Hz, 2H), 7.25 (s, 1H), 7.43 (dd, J = 8.4,
9.4 Hz, 2H), 7.61 (s, 1H), 7.63 (d, J = 8.3 Hz, 2H), 7.84 (s, 1H), 8.31 (s,
1H); dC (CDCl3, 125 MHz) 50.6 (CH2), 103.0, 111.3, 119.2, 121.6,
127.6, 127.8, 128.4, 130.8, 132.4, 134.0, 135.5, 140.53, 142.63; MS
(ESI): m/z = 274 [M+ + H].
1-(1-(4-(Benzo[b]thiophen-5-yl)phenyl)propyl)-1H-
imidazole 12
Synthesized according to method A1 using 12a (1.33 g,
4.94 mmol) and CDI (4.00 g, 24.7 mmol); yield: 0.51 g (32%);
white solid: m.p. 101-1038C; Rf = 0.24 (DCM / MeOH, 20 : 1); IR
(ATR) m (cm– 1) 1496 (m), 1223 (m), 1073 (m), 805 (vs), 758 (s), 702
(s), 663 (s); dH (CDCl3, 500 MHz) 0.98 (t, J = 7.3 Hz, 3H, CH3), 2.28
(q, J = 7.3, 7.6 Hz, 2H, CH2), 5.08 (t, J = 7.6 Hz, 1H, CH), 7.00 (s, 1H),
7.13 (s, 1H), 7.29 (d, J = 8.1 Hz, 2H), 7.39 (d, J = 5.4 Hz, 1H), 7.49 (d, J
= 5.4 Hz, 1H), 7.55 (dd, J = 1.7, 8.4 Hz , 1H), 7.64 (dd, J = 1.7, 8.3 Hz,
2H), 7.73 (s, 1H), 7.93 (d, J = 8.4 Hz, 1H), 8.00 (s, 1H); dC (CDCl3,
125 MHz) 11.1 (CH3), 28.6 (CH2), 63.3 (CH), 117.8, 120.0, 121.9,
122.8, 123.7, 124.0, 127.0, 127.2, 127.8, 128.7, 136.1, 136.7,
138.8, 139.1, 139.4, 140.2, 141.3; MS (ESI): m/z = 319 [M+ + H].
6-(4-(1H-Imidazol-1-ylmethyl)phenyl)benzo[d]thiazole 17
Synthesized according to method A1 using 17a (0.40 g,
1.66 mmol) and CDI (2.15 g, 13.26 mmol); yield: 0.29 g (70%);
white solid: m.p. 1438C; Rf = 0.38 (DCM / MeOH, 95 : 5); IR (ATR) m
(cm– 1) 3370 (w), 2927 (w), 2856 (w), 1708 (w), 1506 (m), 1468 (m),
1441 (m), 1391 (m), 1284 (w), 1232 (m), 1108 (w), 1077 (m), 1030
(w), 886 (w), 813 (s), 739 (s), 697 (w), 663 (s); dH (CDCl3, 500 MHz)
5.18 (s, 2H), 6.95 (s, 1H), 7.13 (s, 1H), 7.23 (d, J = 8.3 Hz, 2H), 7.64
(bs, 1H), 7.71 (dd, J = 1.8 Hz, J = 8.5 Hz, 1H), 8.12 (m, 1H), 8.18 (d, J
= 8.5 Hz, 1H); dC (CDCl3, 125 MHz) 50.6, 119.3, 120.1, 123.8, 125.8,
127.9, 128.0, 134.6, 135.3, 138.1, 140.6, 152.7, 154.3.
5-(4-(1-(1H-Imidazol-1-yl)propyl)phenyl)-1H-indole 13
Synthesized according to method A1 using 13a (1.10 g,
4.38 mmol) and CDI (3.55 g, 21.88 mmol); yield: 0.33 g (25%);
white solid: m.p. 158-1598C; Rf = 0.15 (DCM / MeOH, 20 : 1); IR
(ATR) m (cm– 1) 3143 (br), 1593 (w), 1471 (w), 1222 (w), 1075 (m),
891 (s), 805 (s), 772 (s), 739 (s), 660 (m), 574 (w), 539 (w); dH (CDCl3,
500 MHz) 0.86 (t, J = 7.3, 3H, CH3), 2.15 (q, J = 7.23, 7.6 Hz, 2H,
CH2), 4.93 (t, J = 7.6 Hz, 1H, CH), 6.50 (s, 1H), 6.90 (s, 1H), 7.04 (s,
1H), 7.13–7.17 (m, 3H), 7.30 (dd, J = 8.5, 9.5 Hz, 2H), 7.52 (d, J =
8.3 Hz, 2H), 7.67 (s, 1H), 7.74 (s, 1H), 8.89 (s, 1H); dC (CDCl3,
125 MHz) 11.0 (CH3), 28.4 (CH2), 63.5 (CH), 102.6, 111.4,
119.0,121.4, 125.2, 127.7, 128.4, 130.8, 132.1, 135.6, 135.8, 137.3,
142.6; MS (ESI): m/z = 302 [M+ + H].
1-((4-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)phenyl)-
methyl)-1H-imidazole 18
Synthesized according to method A1 using 18a (0.13 g,
0.54 mmol) and CDI (0.70 g, 4.30 mmol); yield: 0.06 g (43%);
white solid: m.p. 1498C; Rf = 0.52 (DCM / MeOH, 95 : 5); IR (ATR) m
(cm– 1) 3112 (w), 3041 (w), 2930 (w), 2877 (w), 1728 (w), 1677 (w),
1588 (w), 1497 (s), 1309 (s), 1284 (m), 1246 (m), 1068 (s), 897 (m),
876 (w), 807 (m), 748 (m), 699 (w), 662 (w), 530 (w); dH (CDCl3 +
CD3OD, 500 MHz) 5.13 (s, 2H), 6.88 (d, J = 8.3 Hz, 1H), 6.96 (bs,
1H), 7.00–7.04 (m, 3H), 7.18 (d, J = 8.0 Hz, 2H), 7.36 (s, 1H), 7.48
(d, J = 8.0 Hz, 2H), 7.64 (s, 1H); dC (CDCl3 + CD3OD, 125 MHz) 17.8,
29.8, 31.0, 51.1, 64.8, 64.8, 116.0, 117.9, 120.1, 120.3, 127.6,
128.2, 128.9, 134.1, 134.5, 137.6, 141.1, 143.8, 144.1; (ESI): m/z =
293 [M+ + H].
1-(4-(Benzofuran-5-yl)benzyl)-1H-imidazole 14
Synthesized according to method A1 using 14a (0.50 g,
2.23 mmol) and CDI (1.81 g, 11.1 mmol); yield: 0.26 g (43%);
white solid: m.p. 127–1298C; Rf = 0.22 (DCM / MeOH, 20 : 1); IR
(ATR) m (cm– 1) 3109 (w), 1511 (m), 1463 (m), 1439 (m), 1249 (m),
1130 (m), 1107 (m), 1083 (m), 1028 (s), 909 (m), 876 (m), 836 (m),
802 (vs), 779 (s), 748 (vs), 704 (m), 662 (vs), 631 (m), 523 (s); dH
(CDCl3, 500 MHz) 5.17 (s, 2H, CH2), 6.82 (d, J = 3.0 Hz, 1H), 6.95 (s,
1H), 7.12 (s, 1H), 7.23 (d, J = 8.1 Hz, 2H), 7.49 (d, J = 5.4 Hz, 1H),
1-(1-(4-(6-Methoxynaphthalen-2-yl)phenyl)propyl)-1H-
imidazole 19
Synthesized according to method A1 using 19a (0.75 g,
1.71 mmol) and CDI (1.50 g, 9.30 mmol); yield: 0.23 g (39%);
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