JOURNAL OF CHEMICAL RESEARCH 2014 749
3,3,6,6-Tetramethyl-9-p-tolyl-3,4,5,6,7,9-hexahydro-1H-xanthene-
1,8(2H)-dione (3d). White solid; yield 0.169 g (93%); m.p. 212–214 °C;
IR (KBr): νmax =3040, 2930, 2887, 2351, 1667, 1649, 1619, 1583, 1576,
1452, 1362, 1302, 1254, 1192, 1157, 1134, 1122, 1049, 914, 895, 878,
860, 841, 806, 660, 582, 563 cm−1; 1H NMR (400 MHz, CDCl3): δ 7.10
(d, J=8.0 Hz, 2H, ArH), 6.99 (d, J=8.0 Hz, 2H, ArH), 5.52 (s, 1H,
CH), 2.48 (d, J=18.0 Hz, 2H, –CH2), 2.41–2.35 (m, 6H, 3×–CH2), 2.32
(s, 3H, –CH3), 1.25 (s, 6H, 2×–CH3), 1.12 (s, 6H, 2×–CH3). 13C NMR
(100 MHz, CDCl3): δ 190.38, 189.35, 135.22, 134.86, 128.91, 126.62,
115.69, 47.02, 46.40, 32.36, 31.37 (2C), 29.61, 27.34, 20.85. ESI-TOF-
MS: 387.1934 [M+Na]+. Anal. calcd for C24H28O3: C, 79.09; H, 7.74;
found: C, 79.04; H, 7.72%.
3,3,6,6-Tetramethyl-9-(4-nitrophenyl)-3,4,5,6,7,9-hexahydro-1H-
xanthene-1,8(2H)-dione (3e): White solid; yield 0.182 g (92%); m.p.
216–218 °C; IR (KBr): νmax =3067, 2934, 2878, 2339, 1670, 1661, 1585,
1514, 1366, 1299, 1242, 1149, 1124, 1055, 858, 849, 654, 634, 580,
517, 462 cm−1;1H NMR (400 MHz, CDCl3): δ 8.05 (d, J=8.4 Hz, 2H,
ArH), 7.17 (d, J=8.4 Hz, 2H, ArH), 5.48 (s, 1H, –CH), 2.43–2.28 (m,
8H, 4×–CH2), 1.16 (s, 6H, 2×–CH3), 1.04 (s, 6H, 2×–CH3);13C NMR
(100 MHz, CDCl3): δ 196.24, 190.96, 189.53, 162.93, 151.47, 146.56,
146.06, 129.31, 127.60, 123.37 (2C), 114.86, 50.54, 46.94, 46.38, 40.78,
33.19, 32.18, 31.42 (2C), 29.45, 29.19, 27.41; ESI-TOF-MS: 418.1634
[M+Na]+. Anal. calcd for C23H25NO5: C, 69.86; H, 6.37; N, 3.54; found:
C, 69.63; H, 6.37; N, 3.51%.
7.25 (d, J=7.2 Hz, 4H, ArH), 7.10 (t, J=7.2 Hz & 6.8 Hz, 1H, ArH),
5.29 (s, 1H, –CH), 2.24–2.11 (m, 4H, 2×–CH2), 2.07 (d, J= 17.2 Hz,
2H, –CH2), 1.82 (d, J=17.6 Hz, 2H, –CH2), 0.94 (s, 6H, 2×–CH3), 0.79
(s, 6H, 2×–CH3); 13C NMR (100 MHz, CDCl3): δ = 195.73 (2C), 162.19,
159.77, 149.65 (2C), 141.94, 141.91, 138.73, 129.88, 129.31, 129.13 (2C),
129.05, 115.31, 114.65, 114.44, 114.28, 49.96 (2C), 41.59 (2C), 32.19
(2C), 31.95, 29.51 (2C), 26.49 (2C); ESI-TOF-MS: 448.2248 [M+Na]+.
Anal. calcd for C29H31NO2: C, 81.85; H, 7.34; N, 3.29; found: C, 81.81; H,
7.31; N, 3.26%.
9-(4-Fluorophenyl)-3,3,6,6-tetramethyl-10-phenyl-3,4,6,7,9,10-
hexahydroacridine-1,8(2H,5H)-dione (5b): Yellow solid; yield 0.193 g
(87%); m.p. 223–225 °C; IR (KBr): νmax =3053, 2957, 1736, 1639, 1605,
1580, 1501, 1456, 1367, 1302, 1227, 1146, 1034, 841, 770 cm−1; 1H NMR
(400 MHz, CDCl3): δ 7.52–7.45 (m, 3H, ArH), 7.33 (d, J=8.4 Hz, 1H,
ArH), 7.32 (d, J=8.4 Hz, 1H, ArH), 7.16 (d, J=8.0 Hz, 1H, ArH), 7.15
(d, J=7.2 Hz, 1H, ArH), 6.85 (t, J=8.8 Hz, 2H, ArH), 5.18 (s, 1H, –CH),
2.13 (d, J=16.0 Hz, 2H, –CH2), 2.05 (d, J=16.8 Hz, 2H, –CH2), 2.00 (d,
J=17.6 Hz, 2H, –CH2), 1.74 (dd, J=17.6 & 0.4 Hz, 2H, –CH2), 0.87 (s,
6H, 2×–CH3), 0.72 (s, 6H, 2×–CH3); 13C NMR (100 MHz, CDCl3): δ
195.93 (2C), 162.39, 159.97, 149.85 (2C), 142.14, 142.11, 138.93, 130.08,
129.51, 129.34 (2C), 129.25, 114.86 (2C), 114.64, 114.48, 50.16 (2C),
41.79 (2C), 32.40 (2C), 32.16, 29.71 (2C), 26.69 (2C); ESI-TOF-MS:
466.2151 [M+Na]+. Anal. calcd for C29H30FNO2: C, 78.53; H, 6.82; N,
3.16; found: C, 78.59; H, 6.85; N, 3.18%.
9-(4-Hydroxy-3-methoxyphenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-
hexahydro-1H-xanthene-1,8(2H)-dione (3f): White solid, yield 0.172 g
(87%); m.p. 225–226 °C; IR (KBr): νmax =3404, 3045, 2953, 2881,
1661, 1648, 1597, 1591, 1510, 1460, 1277, 1196, 1026, 995, 920, 860,
806, 758, 629, 567, 486, 459 cm−1;1H NMR (400 MHz, CDCl3): δ 6.92
(d, J=1.6 Hz, 1H, ArH), 6.65 (d, J=8.4 Hz, 1H, ArH), 6.51 (dd, J=8.4
& 1.6 Hz, 1H, ArH), 4.59 (s, 1H, –CH), 3.81 (s, 3H, –OCH3), 2.38 (br
s, 4H, 2×–CH2), 2.16 (d, J=16.4 Hz, 2H, –CH2), 2.01 (d, J=16.0 Hz,
2H, –CH2),1.03 (s, 6H, 2×–CH3), 0.93 (s, 6H, 2×–CH3); 13C NMR
(100 MHz, CDCl3): δ 196.66 (2C), 162.13 (2C), 145.92, 144.02, 136.42,
120.05 (2C), 115.79, 113.96, 112.25, 55.87, 50.76 (2C), 40.84 (2C), 32.19
(2C), 31.29, 29.30 (2C), 27.27 (2C); ESI-TOF-MS: 419.4619 [M+Na]+.
Anal. calcd for C24H28O5: C, 72.70; H, 7.12; found: C, 72.68; H, 7.09%.
9-(Benzo[d][1,3]dioxol-5-yl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-
hexahydro-1H-xanthene-1,8(2H)-dione (3g): White solid; yield 0.166 g
(84%); m.p. 221–223 °C; IR (KBr): νmax =3053, 2955, 2928, 2880,
1668, 1659, 1591, 1582, 1479, 1470, 1238, 1190, 1034, 926, 814, 660,
9-(4-Methoxyphenyl)-3,3,6,6-tetramethyl-10-phenyl-3,4,6,7,9,10-
hexahydroacridine-1,8(2H,5H)-dione (5c). Yellow solid; yield 0.207 g
(91%); m.p. 219–221 °C; IR (KBr): νmax =3059, 2935, 2893, 2860,
1634, 1591, 1363, 1259, 1223, 1134, 1028, 935, 833, 708 cm−1; 1H NMR
(400 MHz, CDCl3): δ 7.39 (m, 3H, ArH), 7.19 (dd, J=8.0 & 2.0 Hz,
2H), 7.08 (dd, J=8.0 & 1.6 Hz, 2H), 6.63 (d, J=8.4 Hz, 2H), 5.06 (s,
1H, –CH), 3.58 (s, 3H, –OCH3), 2.05–1.89 (m, 6H, 3×–CH2), 1.65 (d,
J=17.2 Hz, 2H, –CH2), 0.77 (s, 6H, 2×–CH3), 0.64 (s, 6H, 2×–CH3);
13C NMR (100 MHz, CDCl3): δ 195.83 (2C), 157.57 (2C), 149.47 (2C),
138.99 (2C), 138.66 (2C), 129.29 (2C), 128.69 (2C), 114.67 (2C), 113.36
(2C), 55.01, 50.13 (2C), 41.67 (2C), 32.28 (2C), 31.74, 29.62 (2C), 26.66
(2C); ESI-TOF-MS: 478.2361 [M+Na]+. Anal. calcd for C30H33NO3: C,
79.09; H, 7.30; N, 3.07; found: C, 79.03; H, 7.28; N, 3.09.
9-(4-Hydroxy-3-methoxyphenyl)-3,3,6,6-tetramethyl-10-phenyl-
3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione (5d): Yellow solid;
yield 0.203 g (86%); m.p. 224–226 °C; IR (KBr): νmax =3470, 2953,
2930, 2870, 1636, 1618, 1591, 1558, 1273, 1221, 1132, 1040, 935, 812,
754, 706, 669, 631, 599, 571, 542 cm−1; 1H NMR (400 MHz, CDCl3): δ
7.49–7.46 (m, 3H, ArH), 7.15 (dd, J=8.0 & 2.0 Hz, 2H, ArH), 7.06 (s,
1H, ArH), 6.69 (br s, 2H, ArH), 5.13 (s, 1H, –CH), 3.81 (s, 3H, –OCH3),
2.13 (d, J=16.0 Hz, 2H, –CH2), 2.07 (d, J=16.4 Hz, 2H, –CH2), 2.00
(d, J=17.6 Hz, 2H, –CH2), 1.74 (d, J=17.6 Hz, 2H, –CH2), 0.86 (s, 6H,
2×–CH3), 0.74 (s, 6H, 2×–CH3); 13C NMR (100 MHz, CDCl3): δ 196.14
(2C), 149.64 (2C), 145.97, 143.74, 139.06, 138.62, 129.41, 129.28, 125.38,
123.75, 119.33, 114.78 (2C), 113.95 (2C), 111.90, 55.84, 50.21 (2C), 41.79
(2C), 32.39 (2C), 32.12, 29.74 (2C), 26.74 (2C); ESI-TOF-MS: 494.2301
[M+Na]+. Anal. calcd for C30H33NO4: C, 76.41; H, 7.05; N, 2.97; found:
C, 76.43; H, 7.09; N, 2.94.
1
609, 515, 459 cm−1; H NMR (400 MHz, CDCl3): δ 6.73 (d, J=1.6 Hz,
1H, ArH), 6.67 (dd, J=8.4, 1.6 & 1.2 Hz, 1H, ArH), 6.58 (d, J=8.0 Hz,
1H, ArH), 5.79 (s, 2H, –CH2), 4.59 (s, 1H, –CH), 2.38 (s, 4H, 2×–CH2),
2.17 (d, J=16.8 Hz, 2H, –CH2), 2.11 (d, J=16.0 Hz, 2H, –CH2), 1.03 (s,
6H, 2×–CH3), 0.94 (s, 6H, 2×–CH3); 13C NMR (100 MHz, CDCl3): δ
196.39 (2C), 162.07 (2C), 147.27, 145.91, 138.25, 121.50, 115.65, 109.07,
107.81 (2C), 100.70, 50.74 (2C), 40.82 (2C), 32.14 (2C), 31.42, 29.16
(2C), 27.41 (2C); ESI-TOF-MS: 417.1684 [M+Na]+. Anal. calcd for
C24H26O5: C, 73.08; H, 6.64; found: C, 73.13; H, 6.61%.
3,3,6,6-Tetramethyl-9-(3,4,5-trimethoxyphenyl)-3,4,5,6,7,9-
hexahydro-1H-xanthene-1,8(2H)-dione (3h): White solid; yield 0.205 g
(93%); m.p. 184–185 °C; IR (KBr): νmax =3076, 2949, 2932, 2881, 1713,
1664, 1587, 1501, 1454, 1230, 1184, 1126, 1007, 933, 879, 839, 760, 717,
9,10-Bis(4-fluorophenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-
hexahydroacridine-1,8(2H,5H)-dione (5e): Yellow solid; yield 0.210 g
(91%); m.p. 231–233 °C; IR (KBr): νmax =3024, 2951, 2868, 1637, 1578,
1497, 1452, 1364, 1302, 1259, 1221, 1173, 1136, 1028, 1005, 930, 841,
1
673, 615, 577, 511 cm−1; H NMR (400 MHz, CDCl3): δ 6.44 (s, 2H,
ArH), 4.64 (s, 1H, –CH), 3.74 (s, 6H, 2×–OCH3), 3.70 (s, 3H, –OCH3),
2.40–2.33 (m, 4H, 2×–CH2), 2.29–2.16 (m, 4H, 2×–CH2), 1.04 (s, 6H,
2×–CH3), 0.96 (s, 6H, 2×–CH3); 13C NMR (100 MHz, CDCl3): δ 196.43
(2C), 162.30 (2C), 152.74 (2C), 139.68, 136.53, 115.51 (2C), 105.68 (2C),
60.64, 56.05 (2C), 50.69 (2C), 40.85 (2C), 32.74, 32.13, 31.75, 31.05,
29.32 (2C), 27.13; ESI-TOF-MS: 463.2099 [M+Na]+. Anal. calcd for
C26H32O6: C, 70.89; H, 7.32; found: C, 70.93; H, 7.34%.
1
771 cm−1; H NMR (400 MHz, CDCl3): δ 7.29 (td, J=8.0, 6.0, 2.8 Hz,
2H, ArH), 7.20–7.15 (m 4H, ArH), 6.84 (t, J=8.8 & 8.4 Hz, 2H, ArH),
5.17 (s, 1H, –CH), 2.12 (d, J=16.4 Hz, 2H, –CH2), 2.05 (d, J=16.4 Hz,
2H, –CH2), 1.99 (d, J=17.6 Hz, 2H, –CH2), 1.74 (d, J= 17.6 Hz,
2H, –CH2), 0.88 (s, 6H, 2×–CH3), 0.74 (s, 6H, 2×–CH3); 13C NMR
(100 MHz, CDCl3): δ 195.83 (2C), 163.81, 162.42, 161.31, 160.00,
149.63, 141.95, 141.92, 134.92, 134.89, 131.80, 130.92, 129.29, 129.22,
117.28, 114.90, 114.72, 114.68, 50.08 (2C), 41.86 (2C), 32.40 (2C), 32.10,
29.71 (2C), 26.74 (2C); ESI-TOF-MS: 484.2059 [M+Na]+. Anal. calcd
for C29H29F2NO2: C, 75.47; H, 6.33; N, 3.03; found: C, 75.44; H, 6.29; N,
3.06%.
3,3,6,6-Tetramethyl-9,10-diphenyl-3,4,6,7,9,10-hexahydroacridine-
1,8(2H,5H)-dione (5a). Yellow solid; yield 0.179 g (84%); m.p.
251–252 °C; IR (KBr): νmax =3078, 3045, 2955, 2922, 2887, 2853, 1717,
1632, 1578, 1485, 1358, 1265, 1215, 1126, 1074, 1003, 912, 897, 839,
1
798, 733, 694, 671, 606, 584, 573, 528, 461 cm−1; H NMR (400 MHz,
CDCl3): δ 7.56 (d, J=6.4 Hz, 3H, ArH), 7.44 (d, J=7.6 Hz, 2H, ArH),
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