JOURNAL OF CHEMICAL RESEARCH 2010 205
6.68–6.66 (m, 2H), 6.41 (d, 2H, J = 2.5 Hz), 3.40 (s, 6H). Anal. Calcd
for C30H22N2O3: C, 78.59; H, 4.84; N, 6.11. Found: C, 78.45; H, 4.82;
N, 6.26%.
Anal. Calcd for C29H N2O : C, 81.29; H, 4.70; N, 6.54. Found:
C, 81.34; H, 4.76; N, 62.40 6%.2
3k 2-(1H-indol-3-yl)-2-(7-methyl-1H-indol-3-yl)acenaphthylen-
1(2H)-one. IR (KBr) ν 3410 (NH), 3051, 2954, 2922, 2857, 1713,
3f: 2,2-Bis(5-bromo-1H-indol-3-yl)acenaphthylen-1(2H)-one. IR
1
1620, 1600, 1494, 1457, 1431, 1342, 1099, 785, 745 cm−1. H NMR
(KBr) ν 3431 (NH), 3340, 3121, 3051, 1709, 1683, 1600, 1564, 1493,
1
1457, 1417, 1334, 1283, 1096, 884, 794, 783 cm−1. H NMR(500
(500 MHz, DMSO-d ): δ (ppm) 10.97 (s, 1H), 10.93 (s, 1H), 8.35
(d, 1H, J = 8.0 Hz), 68.01–7.94 (m, 2H), 7.89 (t, 1H, J = 7.5 Hz),
7.70–7.67 (m, 1H), 7.55–7.52 (m, 1H), 7.34 (d, 1H, J = 8.0 Hz), 7.07
(d, 1H, J = 8.0 Hz), 7.01–6.98 (m, 1H), 6.83–6.72 (m, 5H), 6.66–6.61
(m, 1H), 2.41 (s, 3H). Anal. Calcd for C29H20N2O: C, 84.44; H, 4.89;
N, 6.79. Found: C, 84.54; H, 4.76; N, 6.83%.
MHz, DMSO-d6): δ (ppm) 11.25 (s, 2H), 8.40 (d, 1H, J = 8.0 Hz),
8.06–8.04 (m, 2H), 7.94–7.91 (m, 1H), 7.75–7.72 (m, 1H), 7.53
(d, 1H, J = 7.0 Hz), 7.35 (d, 2H, J = 9.0 Hz), 7.15–7.13 (m, 4H), 6.93
(d, 2H, J = 2.5 Hz). Anal. Calcd for C H Br N2O: C, 60.46; H, 2.90;
N, 5.04. Found: C, 60.37; H, 3.01; N, 258.1116%.2
3g: 2,2-Bis(7-methyl-1H-indol-3-yl)acenaphthylen-1(2H)-one. IR
(KBr) ν 3425(NH), 3126, 3049, 2967, 2851, 1711, 1598, 1493, 1458,
This work was financially supported by the research
foundation of Hebei University of Science and Technology.
1
1430, 1101, 789, 779, 745 cm−1. H NMR (500 MHz, DMSO-d6): δ
(ppm) 10.93 (s, 2H, NH), 8.35 (d, 1H, J = 8.0 Hz), 7.99 (t, 2H, J = 6.5
Hz), 7.89 (t, 1H, J = 8.0 Hz), 7.67 (t, 1H, J = 8.0 Hz), 7.53 (d, 1H,
J = 7.0 Hz), 6.85–6.79 (m, 6H), 6.65 (t, 2H, J = 7.5 Hz), 2.42 (s, 6H).
Anal. Calcd for C30H22N2O: C, 84.48; H, 5.20; N, 6.57. Found:
C, 84.56; H, 5.13; N, 6.64%.
Received 10 January 2010; accepted 11 March 2010
Paper 100955 doi: 10.3184/030823410X12701382235942
Published online: 29 April 2010
3h: 2,2-Bis(5-nitro-1H-indol-3-yl)acenaphthylen-1(2H)-one. IR
(KBr) ν 3365 (NH), 1706, 1623, 1518, 1470, 1429, 1333, 1256, 1110,
783, 739 cm−1. 1H NMR(500 MHz, DMSO-d ): δ (ppm) 11.83 (s, 2H),
8.45 (d, 1H, J = 8.0 Hz), 8.10 (t, 2H, J = 7.06Hz), 7.98–7.92 (m, 5H),
7.78–7.75 (m, 1H), 7.61 (d, 1H, J = 6.5 Hz), 7.56 (d, 2H, J = 9.0 Hz),
7.24 (d, 2H, J = 2.5 Hz). Anal. Calcd for C H N4O : C, 68.85;
H, 3.30; N, 11.47. Found: C, 68.94; H, 3.22; N, 2181.1364%. 5
The mixture of 4 (0.30 g, 1 mmol), 2 (1 mmol), CAN (0.06 g,
0.1 mmol) and anhydrous C H5OH (10 mL) was refluxed for 1 hour.
After complete conversion a2s indicated by TLC, the reaction mixture
was washed by cool water (3×5 mL) and cool ethanol (3×5 mL). The
crude mixture was purified by flash chromatography to afford the pure
product 3i–k.
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1
1599, 1488, 1457, 1422, 1336, 1250, 1222, 1099, 788, 739 cm−1. H
NMR(500 MHz, DMSO-d6): δ (ppm) 10.98 (s, 1H), 8.36 (d, 1H,
J = 8.0 Hz), 8.00 (t, 2H, J = 8.0 Hz), 7.90 (t, 1H, J = 7.5 Hz), 7.70
(t, 1H, J = 8.0 Hz), 7.55 (d, 1H, J = 6.5 Hz), 7.38–7.34 (m, 2H), 7.07
(t, 2H, J = 7.5 Hz), 7.00 (t, 1H, J = 7.5 Hz), 6.96 (d, 1H, J = 8.5 Hz),
6.86 (d, 1H, J = 2.5 Hz), 6.84 (s, 1H), 6.79 (t, 1H, J = 7.5 Hz), 6.73
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1
1621, 1578, 1482, 1459, 1341, 1255, 1213, 1099, 782, 743 cm−1. H
NMR(500 MHz, DMSO-d ): δ (ppm) 10.97 (s, 1H), 10.82 (s, 1H),
8.37 (d, 1H, J = 8.0 Hz), 8.06 1 (t, 2H, J = 7.5 Hz), 7.91–7.88 (m, 1H),
7.71–7.68 (m, 1H), 7.54 (d, 1H, J = 6.5 Hz), 7.34 (d, 1H, J = 8.5 Hz),
7.23 (d, 1H, J = 8.5 Hz), 6.99 (t, 1H, J = 7.5 Hz), 6.94 (d, 1H, J = 8.0
Hz), 6.89 (d, 1H, J = 2.5 Hz), 6.79 (d, 1H, J = 2.5 Hz), 6.73 (d, 1H,
J = 7.5 Hz), 6.68–6.66 (m, 1H), 6.44 (d, 1H, J = 2.0 Hz), 3.41 (s, 3H).