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Can. J. Chem. Vol. 88, 2010
5-Amino-10,11-bis(3,4-dimethoxyphenyl)-3,3,7,7-
tetramethyl-2,3,4,5,6,7,8,9,10,11-decahydro-1H-
dibenzo[b, f]azepine-1,9-dione (7a)
CH3), 2.30–2.50 (m, 8H, 4 Â CH2), 3.84 (s, 3H, OCH3),
3.88 (s, 3H, OCH3), 5.46 (d, 1H, J = 6.0 Hz), 7.04–7.24 (m,
3H, ArH), 8.26 (s, 1H, NH, exchangeable with D2O). 13C
NMR (DMSO-d6) d: 16.4, 25.3, 27.7, 47.1, 54.2, 56.1,
108.0, 114,1, 130.2, 159.2, 161.6, 197.4. Anal. calcd. for
C25H35NO4: C 72.60, H 8.53, N 3.38; found: C 72.53, H
8.48, N 3.34.
Recrystallized from hot ethanol, mp 270–272 8C. IR
(KBr, cm–1): 3410, 3050, 2954, 2865, 2676, 1578, 1466,
1416, 1366, 1286, 1242, 1158, 1066, 976, 880, 716. 1H
NMR (DMSO-d6) d: 1.14 (s, 6H, 2 Â CH3), 1.22 (s, 6H, 2 Â
CH3), 2.34–2.54 (m, 8H, 4 Â CH2), 3.82 (s, 6H, OCH3),
3.86 (s, 6H, OCH3), 5.42 (d, 2H, J = 6.0 Hz), 7.02–7.24 (m,
6H, ArH), 8.25 (d, 2H, NH). 13C NMR (DMSO-d6) d: 15.4,
19.2, 26.1, 29.6, 47.4, 54.2, 56.1, 112.6, 115.0, 121.2, 133.6,
147.2, 160.4, 197.4. Anal. calcd. for C34H42N2O6: C 71.05,
H 7.36, N 4.87; found: C 72.01, H 7.31, N 4.81.
9-(3,4-Dimethoxyphenyl)-10-hydroxy-3,3,6,6-tetramethyl-
1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione (12a)24
Recrystallized from 95% ethanol, mp 260–262 8C. IR
(KBr, cm–1): 3410, 3068, 2954, 2866, 2674, 1566, 1466,
1428, 1364, 1280, 1260, 1146, 1074, 944, 880, 740. 1H
NMR (DMSO-d6) d: 1.16 (s, 6H, 2 Â CH3), 1.22 (s, 6H, 2 Â
CH3), 2.34–2.54 (m, 8H, 4 Â CH2), 3.84 (s, 3H, OCH3),
3.88 (s, 3H, OCH3), 5.46 (d, 1H, J = 6.0 Hz), 7.02–7.26 (m,
3H, ArH), 10.73 (bs, 1H, OH). 13C NMR (DMSO-d6) d:
15.1, 25.5, 27.2, 47.6, 54.4, 56.1, 108.0, 114.2, 130.2,
159.4, 160.4, 198.4. Anal. calcd. for C25H35NO5: C 69.90,
H 8.21, N 3.26; found: C 69.84, H 8.16, N 3.22.
10,11-Bis(3,4-dimethoxyphenyl)-3,3,7,7-tetramethyl-
1,2,3,4,6,7,8,9,10,11-decahydrodibenzo[b, f]thiepin-1,9-
dione (8a)
Recrystallized from hot ethanol, mp 240–244 8C. IR
(KBr, cm–1): 3426, 3056, 2960, 2864, 2694, 1588, 1470,
1422, 1376, 1298, 1244, 1156, 1068, 976, 880, 700. 1H
NMR (DMSO-d6) d: 1.11 (s, 6H, 2 Â CH3), 1.24 (s, 6H, 2 Â
CH3), 2.34–2.54 (m, 8H, 4 Â CH2), 3.82 (s, 6H, OCH3),
3.86 (s, 6H, OCH3), 5.44 (d, 2H, J = 6.0 Hz), 7.02–7.28 (m,
6H, ArH). 13C NMR (DMSO-d6) d: 15.7, 19.2, 27.2, 29.4,
47.1, 54.2, 56.3, 112.6, 115.0, 121.2, 132.4, 147.4, 160.2,
197.6. Anal. calcd. for C34H40O6S: C 70.80, H 6.99, S 5.66;
found: C 70.74, H 6.92, S 5.61.
10-Amino-9-(3,4-dimethoxyphenyl)-3,3,6,6-tetramethyl-
1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione (13a)
Recrystallized from 95% ethanol, mp 270–272 8C. IR
(KBr, cm–1): 3420, 3042, 2960, 2864, 2672, 1562, 1462,
1424, 1360, 1284, 1242, 1158, 1066, 946, 882, 727. 1H
NMR (DMSO-d6) d: 1.14 (s, 6H, 2 Â CH3), 1.22 (s, 6H, 2 Â
CH3), 2.34–2.54 (m, 8H, 4 Â CH2), 3.84 (s, 3H, OCH3),
3.88 (s, 3H, OCH3), 5.44 (d, 1H, J = 6.0 Hz), 7.06–7.26 (m,
3H, ArH), 8.28 (d, 2H, NH). 13C NMR (DMSO-d6) d: 15.2,
25.4, 27.2, 47.5, 54.1, 56.2, 108.0, 114.4, 132.6, 159.4,
160.2, 197.4. Anal. calcd. for C25H36N2O4: C 70.06, H 8.46,
N 6.53; found: C 70.01, H 8.48, N 6.48.
2-[(4,4-Dimethyl-2,6-dioxocyclohexyl)(3,4-
dimethoxyphenyl)methyl]-5,5-dimethylcyclohexane-1,3-
dione (9a)20
Recrystallized from ethanol, mp 172–176 8C. IR (KBr,
cm–1): 3440, 3090, 2844, 2866, 2564, 1590, 1470, 1440,
1300, 1292, 1232, 1144, 1040, 972, 870, 790. 1H NMR
(DMSO-d6) d: 1.12 (s, 6H, 2 Â CH3), 1.20 (s, 6H, 2 Â
CH3), 2.30–2.52 (m, 8H, 4 Â CH2), 3.82 (s, 3H, OCH3),
3.86 (s, 3H, OCH3), 5.47 (d, 2H, J = 6.0 Hz), 5.70 (1H, s,
CH), 6.96–7.28 (m, 3H, ArH). 13C NMR (DMSO-d6) d:
15.4, 17.7, 26.2, 53.7, 56.4, 68.3, 112.8, 114.4, 119.2,
142.1, 144.4, 147.7, 208.4. Anal. calcd. for C24H30O5: C
72.33, H 7.58; found: C 72.29, H 7.53.
9-(3,4-Dimethoxyphenyl)-3,3,6,6-tetramethyl-
2,3,4,5,6,7,8,9-octahydro-1H thioxanthene-1,8-dione (14a)
Recrystallized from 95% ethanol, mp 234–238 8C. IR
(KBr, cm–1): 3426, 3056, 2960, 2864, 2694, 1588, 1470,
1422, 1376, 1298, 1244, 1156, 1068, 976, 880, 700. 1H
NMR (DMSO-d6) d: 1.11 (s, 6H, 2 Â CH3), 1.24 (s, 6H, 2 Â
CH3), 2.34–2.54 (m, 8H, 4 Â CH2), 3.80 (s, 3H, OCH3),
3.86 (s, 3H, OCH3), 5.44 (d, 1H, J = 6.0 Hz), 7.02–7.28 (m,
3H, ArH). 13C NMR (DMSO-d6) d: 15.2, 22.2, 27.4, 47.2,
54.2, 56.1, 108.0, 114.4, 130.6, 159.2, 160.4, 194.4. Anal.
calcd. for C25H34O4S: C 69.73, H 7.95, S 7.44; found: C
69.68, H 7.88, S 7.38.
9-(3,4-Dimethoxyphenyl)-3,3,6,6-tetramethyl-
2,3,4,5,6,7,8,9-octahydro-1H-xanthene-1,8-dione (10a)20
Recrystallized from 95% ethanol, mp 186–188 8C. IR
(KBr, cm–1): 3222, 3066, 2956, 2866, 2664, 1586, 1474,
1424, 1378, 1288, 1246, 1160, 1064, 976, 856, 740. 1H
NMR (DMSO-d6) d: 1.10 (s, 6H, 2 Â CH3), 1.22 (s, 6H, 2 Â
CH3), 2.34–2.52 (m, 8H, 4 Â CH2), 3.82 (s, 3H, OCH3),
3.86 (s, 3H, OCH3), 5.42 (d, 1H, J = 6.0 Hz), 7.02–7.28 (m,
3H, ArH). 13C NMR (DMSO-d6) d: 15.4, 25.2, 27.1, 47.4,
54.2, 56.1, 108.0, 114.4, 130.6, 159.7, 160.6, 198.4. Anal.
calcd. for C25H34O5: C 72.43, H 8.26; found: C 72.37, H
8.22.
2-[1,2-Bis(4-nitrophenyl)-2-(4,4-dimethyl-2,6-
dioxocyclohexyl)ethyl]-5,5-dimethylcyclohexane-1,3-dione
(3b)
Recrystallized from methanol, mp 238–240 8C. IR (KBr,
cm–1): 3400, 3000, 2966, 2840, 2584, 1560, 1468, 1416,
1360, 1296, 1235, 1144, 1080, 976, 840, 786. 1H NMR
(DMSO-d6) d: 1.10 (s, 6H, 2 Â CH3), 1.20 (s, 6H, 2 Â
CH3), 2.30–2.52 (m, 8H, 4 Â CH2), 5.46 (d, 2H, J =
6.0 Hz), 5.72 (d, 2H, J = 6.0 Hz), 6.96–7.28 (m, 8H, ArH).
13C NMR (DMSO-d6) d: 16.9, 20.3, 28.6, 30.4, 47.5, 112.5,
115.2, 122.4, 131.5, 142.4, 147.5, 150.2, 160.4, 198.6. Anal.
calcd. for C30H32 N2O8: C 65.68, H 5.87, N 5.10; found: C
65.62, H 5.81, N 5.06.
9-(3,4-Dimethoxyphenyl)-3,3,6,6-tetramethyl-
1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione (11a)22
Recrystallized from 95% ethanol, mp 252–256 8C. IR
(KBr, cm–1): 3424, 3066, 2954, 2864, 2686, 1576, 1478,
1422, 1366, 1290, 1248, 1166, 1070, 956, 840, 704. 1H
NMR (DMSO-d6) d: 1.12 (s, 6H, 2 Â CH3), 1.24 (s, 6H, 2 Â
Published by NRC Research Press