Wan et al.
FULL PAPER
Spectral data for compounds
Hz, 1H), 5.05 (dd, J=8.0, 12.0 Hz, 1H), 5.24 (t, J=8.0
Hz, 1H), 6.16—6.18 (m, 1H), 6.30—6.32 (m, 1H), 7.09
—7.56 (m, 6H, Ar-H), 8.11 (brs, NH); IR (KBr) ν: 3420,
1,1'-[(5-Chloro-3-methyl-1-phenyl-1H-pyrazol-4-
ylmethylene)-amino]-thiourea Yellow powder; m.p.
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1
1
3058, 2919, 1620, 1555, 1458, 1378, 1013, 743 cm .
Anal. calcd for C14H12N2O3: C 65.62, H 4.72, N 10.93;
found C 65.54, H 4.85, N 11.03.
236—238 ℃; H NMR (CDCl3, 400 MHz) δ: 2.55 (s,
3H), 2.68 (s, 3H), 7.44—7.68 (m, 10H, Ar-H), 8.01 (s,
1H), 8.05 (s, 1H), 10.19 (s, 1H), 10.64 (s, 1H); 13C
NMR (CDCl3, 100 MHz) δ: 14.78, 112.9, 125.1, 127.5,
128.8, 129.4, 135.3, 137.4, 148.6, 177.7; IR (KBr) ν:
3260, 3134, 2960, 1620, 1543, 1500, 1385, 1004, 763
3-(2-Nitro-1-p-tolylethyl)-1H-indole[2b]
Oil; 1H
NMR (CDCl3, 400 MHz) δ: 2.30 (s, 1H), 4.90 (dd, J=
8.4, 12.4 Hz, 1H), 5.03 (dd, J=7.6, 12.4 Hz, 1H), 5.14
(t, J=8.0 Hz, 1H), 6.98—7.45 (m, 9H, Ar-H), 8.04 (brs,
NH); IR (KBr) ν: 3421, 3054, 2921, 1549, 1551, 1458,
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1
cm . Anal. calcd for C23H20Cl2N8S: C 54.01, H 3.94, N
21.91; found C 54.11, H 3.95, N 21.94.
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1
3-(2-Nitro-1-phenyl-ethyl)-1H-indole[2b] Oil; 1H
NMR (CDCl3, 400 MHz) δ: 4.95 (dd, J=8.4, 12.4 Hz,
1H), 5.07 (dd, J=8.0, 12.4 Hz, 1H), 5.20 (t, J=8.0 Hz,
1H), 7.03—7.46 (m, 10H, Ar-H), 8.11 (brs, NH); IR
(KBr) ν: 3660, 3421, 2927, 1602, 1550, 1457, 1378,
1379, 1101, 745 cm . Anal. calcd for C17H16N2O2: C
72.84, H 5.75, N 9.99; found C 72.74, H 5.73, N 10.04.
3-[1-(4-Methoxy-phenyl)-2-nitro-ethyl]-1H-
1
indole[2b] White powder; m.p. 149—150 ℃; H NMR
(CDCl3, 400 MHz) δ: 3.77 (s, 3H), 4.90 (dd, J=8.4,
12.0 Hz, 1H), 5.05 (dd, J=7.6, 12.0 Hz, 1H), 5.14 (t,
J=8.0 Hz, 1H), 6.83—7.44 (m, 9H, Ar-H), 8.02 (brs,
NH); IR (KBr) ν: 3409, 3056, 2926, 1549, 1510, 1457,
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1
1103, 745 cm . Anal. calcd for C16H14N2O2: C 72.16,
H 3.30, N 10.52; found C 72.21, H 3.24, N 10.59.
3-[1-(4-Chloro-phenyl)-2-nitro-ethyl]-1H-indole[2b]
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1
1
1246, 1180, 748 cm . Anal. calcd for C17H16N2O3: C
68.91, H 5.44, N 9.45; found C 69.01, H 5.48, N 9.53.
3-[2-Nitro-1-(3-nitro-phenyl)-ethyl]-1H-indole[2b]
Oil; H NMR (CDCl3, 400 MHz) δ: 4.91 (dd, J=8.8,
12.4 Hz, 1H), 5.05 (dd, J=7.2, 12.4 Hz, 1H), 5.17 (t,
J=8.0 Hz, 1H), 7.01—7.42 (m, 9H, Ar-H), 8.10 (brs,
NH); IR (KBr) ν: 3420, 3059, 2921, 1620, 1549, 1458,
1
Oil; H NMR (CDCl3, 400 MHz) δ: 4.99 (dd, J=8.8,
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1
12.8 Hz, 1H), 5.11 (dd, J=6.8, 12.8 Hz, 1H), 5.30 (t,
J=7.2 Hz, 1H), 7.07—8.14 (m, 9H, Ar-H), 8.22 (brs,
NH); IR (KBr) ν: 3419, 3063, 2921, 1553, 1526, 1378,
1378, 1092, 746 cm . Anal. calcd for C16H13ClN2O2: C
63.90, H 4.36, N 9.32; found C 63.93, H 4.30, N 9.39.
3-[1-(4-Bromo-phenyl)-2-nitro-ethyl]-1H-indole[2b]
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1
1
1350, 1101, 748 cm . Anal. calcd for C16H13N3O4: C
61.73, H 4.21, N 13.50; found C 61.77, H 4.19, N 13.61.
3-[1-(3-Methoxy-phenyl)-2-nitro-ethyl]-1-methyl-
1H-indole[3a] Oil; 1H NMR (CDCl3, 400 MHz) δ: 3.72
(s, 3H), 3.75 (s, 3H), 4.89 (dd, J=8.4, 12.4 Hz, 1H),
5.03 (dd, J=7.6, 12.4 Hz, 1H), 5.13 (t, J=8.0 Hz, 1H),
6.83—7.45 (m, 9H, Ar-H); IR (KBr) ν: 3052, 2930,
Oil; H NMR (CDCl3, 400 MHz) δ: 4.91 (dd, J=8.8,
12.4 Hz, 1H), 5.05 (dd, J=7.6, 12.4 Hz, 1H), 5.05 (t,
J=8.0 Hz, 1H), 7.01—7.46 (m, 9H, Ar-H), 8.11 (brs,
NH); IR (KBr) ν: 3421, 3058, 2919, 1620, 1551, 1488,
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1
1378, 1104, 745 cm . Anal. calcd for C16H13BrN2O2: C
55.67, H 3.80, N 8.12; found C 55.55, H 3.88, N 8.20.
3-[1-(2,4-Dichloro-phenyl)-2-nitro-ethyl]-1H-
indole[2b] Oil; 1H NMR (CDCl3, 400 MHz) δ: 4.93 (dd,
J=7.2, 12.8 Hz, 1H), 4.99 (dd, J=8.4, 12.8 Hz, 1H),
5.69 (t, J=8.0 Hz, 1H), 7.04—7.47 (m, 8H, Ar-H), 8.13
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1
1551, 1511, 1468, 1376, 1249, 1178, 743 cm . Anal.
calcd for C18H18N2O3: C 69.66, H 5.85, N 9.03; found C
69.57, H 5.79, N 9.02.
1-Methyl-3-(2-nitro-1-phenyl-ethyl)-1H-indole[2b]
(brs, NH); IR (KBr) ν: 3419, 3060, 2923, 1620, 1551,
1
-
1469, 1378, 1103, 745 cm 1. Anal. calcd for
Oil; H NMR (CDCl3, 400 MHz) δ: 4.93 (dd, J=8.4,
12.4 Hz, 1H), 5.05 (dd, J=8.4, 12.4 Hz, 1H), 5.19 (t,
J=4.4 Hz, 1H), 7.05—7.46 (m, 9H, Ar-H); IR (KBr) ν:
3058, 2927, 1552, 1475, 1337, 1332, 1248, 1132, 744
C16H12Cl2N2O2: C 57.33, H 3.61, N 8.36; found C 57.29,
H 3.77, N 8.19.
3-[2-Nitro-1-(2-nitro-phenyl)-2-nitro-ethyl]-1H-
indole[9] Oil; 1H NMR (CDCl3, 400 MHz) δ: 5.24 (dd,
J=8.4, 13.2 Hz, 1H), 5.29 (dd, J=7.2, 13.2 Hz, 1H),
6.04 (t, J=8.0 Hz, 1H), 7.18—7.68 (m, 9H, Ar-H), 8.35
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1
cm . Anal. calcd for C17H16N2O2: C 77.84, H 5.75, N
9.99; found C 77.87, H 5.69, N 9.87.
{4-1-[1-(3-Ethyl-1H-indole-3-yl)-2-nitro-ethyl]-1-
1
phenyl}-dimethyl-amine Oil; H NMR (CDCl3, 400
(brs, NH); IR (KBr) ν: 3421, 3062, 2923, 1620, 1551,
-
1459, 1355, 1106, 745 cm 1. Anal. calcd for
MHz) δ: 2.91 (s, 6H), 3.69 (s, 3H), 4.91(dd, J=8.0, 12.4
Hz, 1H), 5.05 (dd, J=7.6, 12.4 Hz, 1H), 5.12 (t, J=7.6
Hz, 1H), 6.76—7.46 (m, 9H, Ar-H); 13C NMR (CDCl3,
100 MHz) δ: 32.9, 40.5, 40.8, 79.9, 109.4, 112.7, 113.5,
119.1, 119.3, 122.0, 126.3, 126.7, 128.4, 137.2, 149.8;
IR (KBr) ν: 3049, 2915, 1614, 1550, 1522, 1377, 1131,
C16H13N3O4: C 61.73, H 4.21, N 13.50; found C 61.57,
H 4.22, N 13.57.
{4-[1-(1H-Indol-3-yl)-2-nitro-ethyl]-phenyl}-
dimethylamine[3a] Oil; 1H NMR (CDCl3, 400 MHz) δ:
2.92 (s, 6H), 4.88 (dd, J=8.0, 12.0 Hz, 1H), 5.03 (dd,
J=8.0, 12.0 Hz, 1H), 5.10 (t, J=8.0 Hz, 1H), 6.66—
7.47 (m, 9H, Ar-H), 8.05 (brs, NH); IR (KBr) ν: 3429,
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1
1063, 742 cm . Anal. calcd for C19H21N3O2: C 70.57,
H 6.55, N 12.99; found C 70.55, H 6.59, N 12.91.
1-Methyl-3-(2-nitro-1-p-tolyl-ethyl)-1H-indole[2b]
Oil; 1H NMR (CDCl3, 400 MHz) δ: 2.30 (s, 3H), 3.72 (s,
3H), 4.89 (dd, J=8.8, 12.4 Hz, 1H), 5.02 (dd, J=8.0,
12.4 Hz, 1H), 5.13 (t, J=8.0 Hz, 1H), 6.84—7.46 (m,
9H, Ar-H); IR (KBr) ν: 3054, 2919, 1615, 1553, 1475,
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1
3062, 2913, 1544, 1520, 1456, 1379, 1104, 741 cm .
Anal. calcd for C18H19N3O2: C 69.88, H 6.19, N 13.58;
found C 69.92, H 6.24, N 13.52.
3-(1-Furan-2-yl-2-nitro-ethyl)-1H-indole[2b]
Oil;
1H NMR (CDCl3, 400 MHz) δ: 4.91 (dd, J=7.6, 12.4
314
© 2012 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Chin. J. Chem. 2012, 30, 311—315