4
74
D. W. Zhang et al./Chemical Papers 69 (3) 470–478 (2015)
Table 4. Spectral data of newly prepared compounds
Compound
Spectral data
−
Ia
Ib
Ic
IR (KBr), ν˜ /cm 1: 3390, 3050, 2360, 1600, 1450, 1330, 1220, 1090, 1010, 748, 594, 498
1
H NMR (300 MHz, CDCl3), δ: 7.92 (s, 2H, indole NH), 7.37 (dd, J = 10.0 Hz, 7.1 Hz, 7H, indole H4, H7, phenyl
H3, H4, H5), 7.24–7.13 (m, 4H, indole H5, H6), 7.00 (t, J = 7.5 Hz, 2H, phenyl H2, H6), 6.67 (d, J = 1.5 Hz, 2H,
indole H2), 5.89 (s, 1H, CH)
1
3C NMR (CDCl3, 125 MHz), δ: 144.4 (phenyl C1), 137.1, 129.2 (indole C), 128.6, 127.5, 126.6, (phenyl C2, C3,
C4, C5, C6), 124.0, 122.4, 120.4, 120.1, 119.7, 111.5 (indole C), 40.6 (CH)
IR (KBr), ν˜ /cm 1: 3410, 3050, 2360, 1620, 1450, 1340, 1210, 1090, 1010, 744, 598, 482
−
1
H NMR (300 MHz, CDCl3), δ: 7.95 (s, 2H, indole NH), 7.36 (d, J = 8.3 Hz, 8H, indole H4, H6, H7, phenyl H3,
H5), 7.21–7.14 (m, 2H, indole H5), 7.01 (t, J = 7.6 Hz, 2H, phenyl H2, H6), 6.64 (s, 2H, indole H2), 5.86 (s, 1H,
CH)
1
3C NMR (CDCl3, 125 MHz), δ: 143.0 (phenyl C1), 137.1, 132.2 (indole C), 130.5, 128.8, 127.3, (phenyl C2, C3,
C4, C5, C6), 124.0, 122.5, 120.2, 119.8, 119.6, 111.5 (indole C), 40.0 (CH)
IR (KBr), ν˜ /cm 1: 3410, 3050, 2930, 2360, 1740, 1600, 1460, 1340, 1240, 1100, 876, 744, 486
−
1
H NMR (300 MHz, CDCl3), δ: 7.87 (s, 2H, indole NH), 7.38 (dd, J = 18.8 Hz, 8.0 Hz, 4H, indole H4, H7), 7.15
(d, J = 11.7 Hz, 4H, indole H5, H6), 7.02–6.91 (m, 3H, phenyl H4, H5, H6), 6.81 (t, J = 7.3 Hz, 1H, phenyl H3),
6
.67 (s, 2H, indole H2), 6.36 (s, 1H, CH), 3.82 (s, 3H, OCH3)
13
C NMR ((CD3)2SO, 125 MHz), δ: 157.2 (phenyl C2), 137.5, 133.5 (indole C), 130.0, 127.9, 127.6 (phenyl C1, C4,
C6), 124.4, 121.6 (indole C), 120.9 (phenyl C5), 119.8, 119.0 (indole C), 118.7 (phenyl C3), 112.3, 111.7 (indole C),
6.4 (CH), 32.3 (OCH3)
5
−
Id
Ie
If
IR (KBr), ν˜ /cm 1: 3400, 3060, 2950, 2360, 1610, 1510, 1460, 1340, 1240, 1170, 1090, 852, 744, 490
1
H NMR (300 MHz, CDCl3), δ: 7.90 (s, 2H, indole NH), 7.44–7.32 (m, 4H, indole H4, H7), 7.24 (d, J = 5.9 Hz, 2H,
indole H6) 7.16 (t, J = 7.6 Hz, 2H, indole H5), 7.00 (t, J = 7.4 Hz, 2H, phenyl H2, H6), 6.82 (d, J = 8.4 Hz, 2H,
phenyl H3, H5), 6.66 (s, 2H, indole H2), 5.84 (s, 1H, CH), 3.78 (s, 3H, OCH3)
C NMR ((CD3)2SO, 125 MHz), δ: 158.2 (phenyl C4), 137.8, 137.5 (indole C), 130.1, 127.5, 124.3 (phenyl C1, C2,
C6), 121.7, 120.0 (indole C), 119.3 (phenyl C3, C5), 119.0, 114.2, 112.3 (indole C), 55.8 (CH), 39.7 (OCH3)
13
IR (KBr), ν˜ /cm 1: 3410, 3050, 2920, 2360, 1610, 1510, 1450, 1340, 1260, 1210, 1090, 845, 744, 494
−
1
H NMR (300 MHz, CDCl3), δ: 7.92 (s, 2H, indole NH), 7.82 (d, J = 8.4 Hz, 1H, phenyl OH), 7.37 (d, J = 15.5 Hz,
H, indole H4, H7), 7.21–7.10 (m, 4H, indole H5, H6), 7.00 (t, J = 7.5 Hz, 2H, phenyl H2, H6), 6.75 (d, J = 8.4 Hz,
H, phenyl H3, H5), 6.67 (s, 2H, indole-2-CH), 5.83 (s, 1H, CH)
C NMR ((CD3)2SO, 125 MHz), δ: 156.1 (phenyl C4), 137.4, 136.1 (indole C), 123.0, 127.5, 124.2 (phenyl C1, C2,
C6), 121.6, 120.0 (indole C), 119.5 (phenyl C3, C5), 118.9, 115.6, 112.2 (indole C), 39.7 (CH)
4
2
13
IR (KBr), ν˜ /cm 1: 3410, 3060, 2960, 2360, 1620, 1510, 1450,1340, 1210, 1090, 744, 602, 482
−
1
H NMR (300 MHz, CDCl3), δ: 7.89 (s, 2H, indole NH), 7.38 (dd, J = 17.2 Hz, 8.0 Hz, 4H, indole H4, H7), 7.27
(d, J = 3.8 Hz, 4H, indole H5, H6), 7.16 (t, J = 7.5 Hz, 2H, phenyl H3, H5), 7.00 (t, J = 7.4 Hz, 2H, phenyl H2,
H6), 6.68 (s, 2H, indole H2), 5.86 (s, 1H, CH), 1.29 (s, 9H, C(CH3)3)
1
3C NMR (CDCl3, 125 MHz), δ: 148.6, 140.7 (phenyl C1, C4), 137.5, 136.6, 128.2 (indole C), 127.1 (phenyl C3,
C5), 125.0 (indole C), 123.5, 121.8 (phenyl C2, C6), 119.9, 119.1, 110.9 (indole C), 39.6 (CH), 31.4 (C(CH3)3)
MS, m/z: 377.2 [M – H]+ (calc. 377.2)
IR (KBr), ν˜ /cm 1: 3410, 3160, 2360, 1720, 1580, 1450, 1340, 1100, 741, 509
−
Ig
1
H NMR (300 MHz, CDCl3), δ: 8.65 (d, J = 2.2 Hz, 1H, pyridyl H2), 8.51–8.43 (m, 1H, pyridyl H4), 8.03 (s, 2H,
indole NH), 7.64 (d, J = 7.9 Hz, 1H, pyridyl H6), 7.37 (dd, J = 7.8 Hz, 4.3 Hz, 4H, indole H4, H7), 7.23–7.14 (m,
3H, pyridyl H5, indole H6), 7.02 (ddd, J = 8.1 Hz, 7.1 Hz, 1.0 Hz, 2H, indole H5), 6.68 (s, 2H, indole H2), 5.93 (s,
1
H, CH)
1
3
C NMR ((CD3)2SO, 125 MHz), δ: 150.5, 148.0, 141.1, (pyridyl C2, C4, C6), 137.5, 136.4 (indole C), 127.3, 124.5,
pyridyl C1, C5), 124.1, 121.9, 119.8, 119.2, 118.0, 112.4 (indole C), 38.0 (CH)
MS, m/z: 324.2 [M + H] (calc. 324.15)
(
+
−
Ih
Ii
IR (KBr), ν˜ /cm 1: 3420, 3060, 2850, 1920, 1620, 1520, 1350, 1220, 1160, 1090, 899, 791, 733, 602, 474
1
H NMR (300 MHz, CDCl3), δ: 8.21 (s, 1H, phenyl H2), 8.08 (d, J = 8.7 Hz, 1H, phenyl H4), 7.99 (s, 2H, indole
NH), 7.70 (d, J = 7.9 Hz, 1H, phenyl H6), 7.41 (dt, J = 17.6 Hz, 8.4 Hz, 5H, phenyl H5, indole H4, H7), 7.20 (t, J
7.5 Hz, 2H, indole H6), 7.02 (t, J = 7.5 Hz, 2H, indole H5), 6.68 (s, 2H, indole H2), 6.00 (s, 1H, CH)
C NMR (DMSO, 125 MHz), δ: 148.7, 148.3 (phenyl C1, C3), 137.5 (indole C), 136.0, 130.4 (phenyl C5, C6), 127.2
=
13
(
indole C), 124.7 (phenyl C2), 123.5, 122.0, 119.8, 119.3, 117.8, 112.5 (indole C), 40.0 (CH)
IR (KBr), ν˜ /cm 1: 3410, 3048, 2862, 1910, 1717, 1616, 1508, 1454, 1339, 1215, 1092, 845, 741, 579, 474
−
1
H NMR (600 MHz, CDCl3), δ: 7.79 (s, 2H, indole NH), 7.38 (d, J = 7.9 Hz, 2H, indole H4, H7), 7.30 (d, J =
8
2
3
.2 Hz, 2H, indole H4), 7.23–7.20 (m, 2H, phenyl H3, H5), 7.14 (t, J = 7.5 Hz, 2H, phenyl H2, H6), 7.07–7.05 (m,
H, indole H6), 6.98 (t, J = 7.5 Hz, 2H, indole H5), 6.59 (d, J = 1.8 Hz, 2H, indole H2), 5.83 (s, 1H, CH), 2.30 (s,
H, CH3)
13
C NMR (CDCl3, 125 MHz), δ: 141.0 (indole C), 136.7, 135.5, 129.0, 128.6 (phenyl C1, C2, C3, C4, C5, C6), 127.1,
23.6, 121.9, 120.0, 119.9, 119.2, 111.1 (indole C), 39.8 (CH), 21.1 (CH3)
1
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