May-Jun 2008
An Efficient Synthesis of Polyhydroacridine Derivatives
657
3,3,6,6-Tetramethyl-9-(4-methylphenyl)-10-(4-methoxy-
phenyl)-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione (4d).
This compound was obtained as solid with mp 247-248 °C; ir
(potassium bromide): 2959, 2841, 1640, 1575, 1511, 1466,
1424, 1360, 1310, 1294, 1277, 1245, 1213, 1175, 1141, 1120,
= 2.0 Hz, 1H, ArH), 7.54 (d, J = 8.4 Hz, 1H, ArH). Anal. Calcd.
for C30H31Cl2NO3: C, 68.70; H, 5.96; N, 2.67. Found: C, 68.82;
H, 6.04; N, 2.75.
3,3,6,6-Tetramethyl-9-(4-hydroxyphenyl)-10-(4-methoxy-
phenyl)-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione (4i).
This compound was obtained as solid with mp > 300 °C; ir
(potassium bromide): 3234, 2960, 2873, 1634, 1593, 1567, 1510,
1452, 1366, 1313, 1295, 1251, 1213, 1168, 1142, 1121, 1107,
1
1029, 1000, 849, 835 cm-1; H nmr (DMSO-d6): δ 0.72 (s, 6H, 2
× CH3), 0.89 (s, 6H, 2 × CH3), 1.79 (d, J = 17.6 Hz, 2H, 2 ×
CH), 1.99 (d, J = 16.0 Hz, 2H, 2 × CH), 2.18 (d, J = 16.0 Hz,
2H, 2 × CH), 2.20 (d, J = 17.6 Hz, 2H, 2 × CH), 2.22 (s, 3H,
CH3), 3.86 (s, 3H, CH3O), 5.00 (s, 1H, CH), 7.04 (d, J = 7.6 Hz,
2H, ArH), 7.13 (d, J = 8.0 Hz, 2H, ArH), 7.18 (d, J = 8.0 Hz,
2H, ArH), 7.20-7.40 (m, 2H, ArH). Anal. Calcd. for C31H35NO3:
C, 79.28; H, 7.51; N, 2.98. Found: C, 79.35; H, 7.43; N, 3.06.
3,3,6,6-Tetramethyl-9-(3,4-dimethoxyphenyl)-10-(4-meth-
oxyphenyl)-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione
(4e). This compound was obtained as solid with mp 247-248 °C;
ir (potassium bromide): 2955, 2837, 1636, 1573, 1510, 1465,
1419, 1363, 1311, 1294, 1248, 1213, 1174, 1138, 1024, 977,
928, 853, 815, 775, 754 cm-1; 1H nmr (DMSO-d6): δ 0.75 (s, 6H,
2 × CH3), 0.89 (s, 6H, 2 × CH3), 1.81 (d, J = 17.2 Hz, 2H, 2 ×
CH), 2.02 (d, J = 16.0 Hz, 2H, 2 × CH), 2.19 (d, J = 16.0 Hz,
2H, 2 × CH), 2.21 (d, J = 17.2 Hz, 2H, 2 × CH), 3.69 (s, 3H,
CH3O), 3.71 (s, 3H, CH3O), 3.85 (s, 3H, CH3O), 5.00 (s, 1H,
CH), 6.79-6.84 (m, 3H, ArH), 7.14 (s, 3H, ArH), 7.37 (s, 1H,
ArH). Anal. Calcd. for C32H37NO5: C, 74.54; H, 7.23; N, 2.72.
Found: C, 74.63; H, 7.19; N, 2.64.
1
1030, 1001, 887, 844, 745 cm-1; H nmr (DMSO-d6): δ 0.72 (s,
6H, 2 × CH3), 0.88 (s, 6H, 2 × CH3), 1.78 (d, J = 17.2 Hz, 2H, 2 ×
CH), 1.99 (d, J = 16.0 Hz, 2H, 2 × CH), 2.17 (d, J = 16.0 Hz, 2H,
2 × CH), 2.18 (d, J = 17.2 Hz, 2H, 2 × CH), 3.85 (s, 3H, CH3O),
4.93 (s, 1H, CH), 6.61 (d, J = 8.4 Hz, 2H, ArH), 7.07 (d, J = 8.4
Hz, 2H, ArH), 7.12 (d, J = 8.4 Hz, 2H, ArH), 7.21 (s, 1H, ArH),
7.36 (s, 1H, ArH), 9.09 (s, 1H, OH). Anal. Calcd. for C30H33NO4:
C, 76.41; H, 7.05; N, 2.97. Found: C, 76.59; H, 6.97; N, 3.06.
3,3,6,6-Tetramethyl-9-(4-bromophenyl)-10-(3-chloro-4-
methylphenyl)-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-
dione (4j). This compound was obtained as solid with mp 293-
295 °C; ir (potassium bromide): 2957, 1652, 1603, 1567, 1495,
1372, 1301, 1264, 1224, 1176, 1143, 1117, 1068, 1055, 1009, 923,
887, 838, 775, 731, 708 cm-1; 1H nmr (DMSO-d6): δ 0.73 (s, 6H, 2
× CH3), 0.90 (s, 6H, 2 × CH3), 1.80 (d, J = 16.0 Hz, 2H, 2 × CH),
2.01 (d, J = 16.0 Hz, 2H, 2 × CH), 2.18 (d, J = 16.0 Hz, 4H, 4 ×
CH), 2.44 (s, 3H, CH3), 4.99 (s, 1H, CH), 7.27 (d, J = 8.4 Hz, 2H,
ArH), 7.34-7.37 (m, 1H, ArH), 7.43 (d, J = 8.4 Hz, 2H, ArH), 7.59
(d, J = 8.0 Hz, 2H, ArH). 13C nmr (DMSO-d6): δ 19.40, 26.17,
29.19, 31.96, 40.87, 49.51, 112.61, 125.79, 129.77, 129.85,
130.57, 130.69, 136.95, 137.01, 145.34, 150.12, 150.83, 151.19,
194.74. Anal. Calcd. for C30H31BrClNO2: C, 65.17; H, 5.65; N,
2.53. Found: C, 65.28; H, 5.60; N, 2.57.
3,3,6,6-Tetramethyl-9-(4-(dimethylamino)phenyl)-10-(4-
methoxyphenyl)-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-
dione (4f). This compound was obtained as solid with mp 274-
276 °C; ir (potassium bromide): 2961, 1652, 1603, 1577, 1518,
1461, 1370, 1295, 1250, 1223, 1169, 1132, 1113, 1026, 999,
1
979, 945, 887, 850, 827, 778, 745 cm-1; H nmr (DMSO-d6): δ
3,3,6,6-Tetramethyl-9-(4-chlorophenyl)-10-(3-chloro-4-methyl-
phenyl)-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione (4k).
This compound was obtained as solid with mp 288-290 °C; ir
(potassium bromide): 2958, 2870, 1642, 1601, 1578, 1489, 1472,
1361, 1301, 1261, 1221, 1176, 1143, 1122, 1089, 1054, 1014,
1000, 924, 887, 840 cm-1; 1H nmr (DMSO-d6): δ 0.72 (s, 6H, 2 ×
CH3), 0.89 (s, 6H, 2 × CH3), 1.80 (d, J = 16.0 Hz, 2H, 2 × CH),
2.00 (d, J = 16.0 Hz, 2H, 2 × CH), 2.18 (d, J = 16.0 Hz, 4H, 4 ×
CH), 2.44 (s, 3H, CH3), 5.00 (s, 1H, CH), 7.27-7.34 (m, 5H, ArH),
7.59 (d, J = 8.0 Hz, 2H, ArH). Anal. Calcd. for C30H31Cl2NO2: C,
70.86; H, 6.15; N, 2.75. Found: C, 70.92; H, 6.11; N, 2.84.
0.74 (s, 6H, 2 × CH3), 0.89 (s, 6H, 2 × CH3), 1.79 (d, J = 17.2
Hz, 2H, 2 × CH), 1.99 (d, J = 16.0 Hz, 2H, 2 × CH), 2.17 (d, J =
16.0 Hz, 2H, 2 × CH), 2.19 (d, J = 17.2 Hz, 2H, 2 × CH), 3.22
(s, 6H, (CH3)2N), 3.86 (s, 3H, CH3O), 4.92 (s, 1H, CH), 6.61 (d,
J = 8.4 Hz, 2H, ArH), 7.10-7.14 (m, 4H, ArH), 7.20-7.36 (m,
2H, ArH). Anal. Calcd. for C32H38N2O3: C, 77.08; H, 7.68; N,
5.62. Found: C, 77.23; H, 7.62; N, 5.58.
3,3,6,6-Tetramethyl-9-(4-chlorophenyl)-10-(4-methoxy-
phenyl)-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione (4g).
This compound was obtained as solid with mp 274-276 °C; ir
(potassium bromide): 2956, 1646, 1572, 1510, 1471, 1360,
1295, 1242, 1222, 1169, 1143, 1120, 1036, 1003, 934, 886, 846,
798, 750, 718, 700, 662 cm-1; 1H nmr (DMSO-d6): δ 0.74 (s, 6H,
2 × CH3), 0.87 (s, 6H, 2 × CH3), 1.79 (d, J = 17.2 Hz, 2H, 2 ×
CH), 1.94 (d, J = 16.4 Hz, 2H, 2 × CH), 2.15 (d, J = 16.4 Hz,
4H, 4 × CH), 3.86 (s, 3H, CH3O), 5.27 (s, 1H, CH), 7.08-7.17
(m, 3H, ArH), 7.22-7.38 (m, 4H, ArH), 7.50 (d, J = 8.0 Hz, 1H,
ArH). Anal. Calcd. for C30H32ClNO3: C, 73.53; H, 6.58; N, 2.86.
Found: C, 73.66; H, 6.51; N, 2.82.
3,3,6,6-Tetramethyl-9-(4-methylphenyl)-10-(3-chloro-4-
methylphenyl)-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione
(4l). This compound was obtained as solid with mp 248-250 °C; ir
(potassium bromide): 2957, 2869, 1642, 1602, 1578, 1495, 1472,
1361, 1301, 1260, 1221, 1177, 1143, 1122, 1053, 999, 886, 835,
715, 702 cm-1; 1H nmr (DMSO-d6): δ 0.73 (s, 6H, 2 × CH3), 0.89
(s, 6H, 2 × CH3), 1.79 (d, J = 16.0 Hz, 2H, 2 × CH), 2.00 (d, J =
16.0 Hz, 2H, 2 × CH), 2.17 (d, J = 16.0 Hz, 4H, 4 × CH), 2.22 (s,
3H, CH3), 2.44 (s, 3H, CH3), 4.99 (s, 1H, CH), 7.02-7.05 (m, 3H,
ArH), 7.19 (d, J = 8.0 Hz, 2H, ArH), 7.31 (s, 1H, ArH), 7.59 (d, J
= 8.0 Hz, 1H, ArH). Anal. Calcd. for C31H34ClNO2: C, 76.29; H,
7.02; N, 2.87. Found: C, 76.40; H, 6.98; N, 2.94.
3,3,6,6-Tetramethyl-9-(3,4-dichlorophenyl)-10-(4-methoxy-
phenyl)-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione (4h).
This compound was obtained as solid with mp 209-211 °C; ir
(potassium bromide): 2959, 1645, 1573, 1513, 1456, 1376,
1294, 1250, 1206, 1169, 1132, 1027, 932, 876, 847, 779, 745,
702, 673 cm-1; 1H nmr (DMSO-d6): δ 0.73 (s, 6H, 2 × CH3), 0.89
(s, 6H, 2 × CH3), 1.83 (d, J = 17.2 Hz, 2H, 2 × CH), 2.03 (d, J =
16.0 Hz, 2H, 2 × CH), 2.20 (d, J = 16.0 Hz, 2H, 2 × CH), 2.21
(d, J = 17.2 Hz, 2H, 2 × CH), 3.86 (s, 3H, CH3O), 5.00 (s, 1H,
CH), 7.14 (d, J = 7.2 Hz, 2H, ArH), 7.24 (s, 1H, ArH), 7.27 (dd,
J1 = 2.0 Hz, J2 = 8.4 Hz, 1H, ArH), 7.37 (s, 1H, ArH), 7.45 (d, J
3,3,6,6-Tetramethyl-9-(thiophen-2-yl)-10-(4-methoxyphenyl)-
1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione (4m). This
compound was obtained as solid with mp 240-242 °C; ir
(potassium bromide): 3064, 2959, 2837, 1651, 1573, 1506,
1441, 1371, 1293, 1264, 1213, 1173, 1121, 1074, 1030, 997,
1
980, 921, 888, 843, 820, 772, 744, 699 cm-1; H nmr (DMSO-
d6): δ 0.78 (s, 6H, 2 × CH3), 0.91 (s, 6H, 2 × CH3), 1.78 (d, J =
17.6 Hz, 2H, 2 × CH), 2.07 (d, J = 16.0 Hz, 2H, 2 × CH), 2.23