160 J. Chin. Chem. Soc., Vol. 57, No. 2, 2010
Mo and Chen
rated to give the crude product. The crude product was pu-
rified by flash chromatography (ethyl acetate/petroleum
ether, 1:20) to afford the pure product.
72.28; H, 5.10; N, 3.37. Found: C, 72.40; H, 5.22; N, 3.18.
12-p-Tolyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one
(4q)
12-(2-Hydroxyphenyl)-9,9-dimethyl-8,9,10,12-tetrahy-
drobenzo[a]xanthen-11-one (4d)
Colourless crystals; IR (KBr): 2950, 2871, 1650,
1596, 1456, 1401, 1373, 1336, 1251, 1227, 1200, 1188,
1126, 1138, 955, 818 cm-1; 1H NMR (400 MHz, CDCl3) dH
1.91-1.94 (m, 2H), 2.21 (s, 3H), 2.31-2.48 (m, 2H), 2.56-
2.77 (m, 2H), 5.70 (s, 1H), 6.98 (d, J = 8.0 Hz, 1H), 7.03 (d,
J = 8.0 Hz, 1H), 7.20 (d, J = 8.0 Hz, 1H), 7.25 (d, J = 8.0
Hz, 1H), 7.30-7.45 (m, 3H), 7.76 (t, J = 8.0 Hz, 2H), 7.97
(d, J = 8.0 Hz, 1H); Anal. calcd. For C24H20O2: C, 84.68; H,
5.92. Found: C, 84.82; H, 5.78.
Colourless crystals; IR (KBr): 3421, 2960, 2866,
1652, 1631, 1595, 1558, 1485, 1379, 1363, 1232, 1182,
1070, 812, 754 cm-1; 1H NMR (400 MHz, CDCl3) dH 0.99
(s, 3H), 1.14 (s, 3H), 2.35 and 2.42 (AB system, J = 16.4
Hz, 2H), 2.61 (s, 2H), 5.76 (s, 1H), 6.58-6.64 (m, 2H),
6.97-7.02 (m, 2H), 7.32-7.42 (m, 3H), 7.67 (d, J = 8.0 Hz,
1H), 7.77 (t, J = 8.4 Hz, 2H), 9.26 (s, 1H); ESI MS (m/z) =
371 (M+H); Anal. calcd. For C25H22O3: C, 81.06; H, 5.99.
Found: C, 79.95; H, 6.06.
12-(4-Methoxyphenyl)-8,9,10,12-tetrahydrobenzo[a]-
xanthen-11-one (4r)
Colourless crystals, Mp 181-182 oC; IR (KBr): 2945,
2833, 1651, 1595, 1460, 1378, 1251, 1227, 1188, 1175,
12-(3-Phenoxyphenyl)-9,9-dimethyl-8,9,10,12-tetrahy-
drobenzo[a]xanthen-11-one (4g)
1
1130, 1034, 952, 829, 748 cm-1; H NMR (400 MHz,
Colourless crystals; IR (KBr): 2929, 2832, 1651,
1591, 1577, 1485, 1444, 1398, 1373, 1236, 1178, 1024,
831, 817, 742 cm-1; 1H NMR (400 MHz, CDCl3) dH 0.99 (s,
3H), 1.13 (s, 3H), 2.26 and 2.32 (AB system, J = 16.4 Hz,
2H), 2.56 (s, 2H), 5.68 (s, 1H), 6.67-6.70 (m, 1H), 6.85 (d,
J = 8.4 Hz, 2H), 7.01-7.06 (m, 2H), 7.11-7.16 (m, 2H),
7.23-7.33 (m, 3H), 7.39 (t, J = 8.0 Hz, 1H), 7.46 (t, J = 8.0
Hz, 1H), 7.75 (d, J = 8.4 Hz, 1H), 7.79 (d, J = 8.0 Hz, 1H),
7.98 (d, J = 8.4 Hz, 1H); ESI MS (m/z) = 447 (M+H); Anal.
calcd. For C31H26O3: C, 83.38; H, 5.87. Found: C, 83.26; H,
6.02.
CDCl3) dH 1.91-2.08 (m, 2H), 2.31-2.48 (m, 2H), 2.57-2.76
(m, 2H), 3.69 (s, 3H), 5.69 (s, 1H), 6.71 (d, J = 8.0 Hz, 2H),
7.23-7.45 (m, 5H), 7.77 (t, J = 8.4 Hz, 2H), 7.96 (d, J = 8.4
Hz, 1H); Anal. calcd. For C24H20O3: C, 80.88; H, 5.66.
Found: C, 81.02; H, 5.53.
12-(4-Bromophenyl)-8,9,10,12-tetrahydrobenzo[a]xan-
then-11-one (4v)
Colourless crystals; IR (KBr): 2823, 1647, 1595,
1473, 1375, 1224, 1190, 1175, 1130, 1066, 954, 812, 746
cm-1; 1H NMR (400 MHz, CDCl3) dH 1.93-2.09 (m, 2H),
2.32-2.51 (m, 2H), 2.62-2.79 (m, 2H), 5.70 (s, 1H), 7.05 (t,
J = 8.0 Hz, 1H), 7.20 (d, J = 8.0 Hz, 1H), 7.32-7.35 (m, 2H),
7.39 (t, J = 7.6 Hz, 2H), 7.45 (t, J = 8.0 Hz, 1H), 7.78 (d, J =
8.4 Hz, 1H), 7.80 (d, J = 8.0 Hz, 1H), 7.89 (d, J = 8.4 Hz,
1H); Anal. calcd. For C23H17BrO2: C, 68.16; H, 4.23.
Found: C, 68.32; H, 4.05.
12-(4-Fluorophenyl)-9,9-dimethyl-8,9,10,12-tetrahydro-
benzo[a]xanthen-11-one (4h)
Colourless crystals; IR (KBr): 3037, 2889, 1651,
1595, 1508, 1398, 1375, 1226, 1184, 1026, 852, 839, 744
cm-1; 1H NMR (400 MHz, CDCl3) dH 0.96 (s, 3H), 1.12 (s,
3H), 2.25 and 2.30 (AB system, J = 16.4 Hz, 2H), 2.57 (s,
2H), 5.70 (s, 1H), 6.85 (d, J = 8.8 Hz, 2H), 7.28-7.46 (m,
5H), 7.78 (t, J = 8.0 Hz, 2H), 7.93 (d, J = 8.4 Hz, 1H); Anal.
calcd. For C25H21FO2: C, 80.62; H, 5.68. Found: C, 80.51;
H, 5.80.
ACKNOWLEDGMENT
We thank the Nature Science Foundation of Hebei
Province (B2008000149) and the Science Foundation of
Hebei Normal University for financial support.
2-(4-Hydroxy-3-nitrophenyl)-9,9-dimethyl-8,9,10,12-
tetrahydrobenzo[a]xanthen-11-one (4o)
Yellow crystals; IR (KBr): 3145, 3024, 2956, 1651,
1
Received February 1, 2010.
1596, 1400, 1375, 1224, 1174, 1145, 827, 754 cm-1; H
REFERENCES
NMR (400 MHz, CDCl3) dH 0.97 (s, 3H), 1.13 (s, 3H), 2.25
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(s, 1H), 6.98 (d, J = 8.8 Hz, 1H), 7.34 (d, J = 8.8 Hz, 1H),
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= 8.8 Hz, 1H), 8.03 (d, J = 2.4 Hz, 1H), 10.43 (s, 1H); ESI
MS (m/z) = 416 (M+H); Anal. calcd. For C25H21NO5: C,
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