JOURNAL OF CHEMICAL RESEARCH 2015 449
2
1
4
(
4
H, PhH), R : 7.09–7.68 (m, 4H, PhH); IR (KBr): 1640 (C=O), 1571
H NMR (DMSO-d , 400 MHz) δ 0.72 (s, 6H, -2CH ), 0.89 (s, 6H,
6
3
-1
C=C), 1362 (C–N) cm . Anal. calcd for C H Cl NO : C, 68.50; H,
-2CH ), 1.76–2.23 (m, 8H, 2a-H, 7a-H, 2b-H, 7b-H, 4a-H, 5a-H, 4b-
H, 5b-H), 5.04 (s, 1H, 9-H), 7.08–7.32 (m, 5H, PhH), R : 7.45–7.70 (m,
4H, PhH); IR (KBr): 1632 (C=O), 1571 (C=C), 1370 (C–N) cm . Anal.
calcd for C H ClNO : C, 75.72; H, 6.57; N, 3.04; found: C, 75.61; H,
6.45; N, 2.99%.
2
5
21
2
2
3
2
.83; N, 3.20; found: C, 68.41; H, 4.64; N, 3.14%.
- (2-Chlorophenyl) -10- (naphthalen-1-yl) -3,4,6,7,9,10-
hexahydroacridine-1,8(2H,5H)-dione (3f): Yield 0.328 g (73%); grey
-1
9
2
9
30
2
+
1
powder; m.p. 260–262 ˚C; MS (ESI) m/z 454.0 [M+H] . H NMR
(
DMSO-d , 400 MHz) δ 2.05–2.94 (m, 12H, 3a-H, 6a-H, 3b-H, 6b-
4.4.14 9-(4-Methoxyphenyl)-3,3,6,6-tetramethyl-10-phenyl-3,4,
,7,9,10-hexahydro-acridine-1,8(2H,5H)-dione (3n): Yield 0.319
6
H, 2a-H, 7a-H, 2b-H, 7b-H, 4a-H, 5a-H, 4b-H, 5b-H), 3.78 (m, 1H,
9
(
C H ClNO : C, 76.73; H, 5.33; N, 3.09; found: C, 76.55; H, 5.24; N,
3
6
2
-H), 5.92–6.36(m, 4H, PhH); R : 6.47–7.51 (m, 7H, NaphH); IR
g (70%); yellow powder; m.p. 238–240 ˚C; MS (ESI) m/z 456.3
-1
KBr): 1637 (C=O), 1571 (C=C), 1355 (C–N) cm . Anal. calcd for
+
1
[
M+H] . H NMR (DMSO-d , 400 MHz) δ 0.62 (s, 6H, -2CH ),
6
3
2
9
24
2
0.77 (s, 6H, -2CH ), 1.62–1.66 (m, 2H, 2a-H, 7a-H), 1.89–1.92 (m,
3
.01%.
-(p-Tolyl)-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione
3g): Yield 0.218 g (71%); light yellow powder; m.p. 294–296 ˚C; MS
3
(
7
H, 2b-H, 7b-H, 4a-H), 2.06-2.12 (m, 3H, 5a-H, 4b-H, 5b-H), 4.88
9
1
2
s, 1H, 9-H), 6.70–7.13 (m, 4H, PhH); R : 3.59 (s, 3H, 4´-OCH ); R :
3
(
(
(
.30–7.54 (m, 5H, PhH); IR (KBr): 1643 (C=O), 1577 (C=C), 1362
+
1
ESI) m/z 308.3 [M+H] . H NMR (DMSO-d , 400 MHz) δ 1.61–1.89
-1
6
(C–N) cm . Anal. calcd for C H NO : C, 79.09; H, 7.30; N, 3.07;
30 33 3
m, 5H, 3a-H, 6a-H, 3b-H, 6b-H, 2a-H), 2.03–2.16 (m, 7H, 7a-H, 2b-H,
found: C, 79.01; H, 7.18; N, 3.02%.
.4.15 10-(4-Chlorophenyl)-9-(4-methoxyphenyl)-3,3,6,6-tetramethyl-
7
b-H, 4a-H, 5a-H, 4b-H, 5b-H), 4.75 (s, 1H, 9-H), 6.84–6.93 (m, 4H,
4
1
PhH), 9.29 (s, 1H, 10-NH); R : 2.40 (s, 3H, 4´-CH ); IR (KBr): 1643
(
3
3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione (3o): Yield 0.347 g
-1
C=O), 1570 (C=C), 1369 (C–N) cm . Anal. calcd for C H NO C,
+
2
0
21
2 :
(71%); yellow powder; m.p. 240–242 ˚C; MS (ESI) m/z 490.4 [M+H] .
7
8.15; H, 6.89; N, 4.56; found: C: 78.11; H:6.73; N: 4.40%.
0-Phenyl-9-(p-tolyl)-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-
dione (3h): Yield 0.291 g (76%); pale grey powder; m.p. 256–258
1
H NMR (DMSO-d , 400 MHz) δ 0.82 (s, 6H, -2CH ), 0.96 (s, 6H, -2CH ),
6
3
3
1
1
(
.78–1.83 (m, 2H, 2a-H, 7a-H), 2.03–2.07 (m, 2H, 2b-H, 7b-H), 2.13–2.18
m, 4H, 4a-H, 5a-H, 4b-H, 5b-H), 5.20 (s, 1H, 9-H), 6.77–7.26 (m, 4H,
+
1
˚C; MS (ESI) m/z 384.4[M+H] . H NMR (DMSO-d , 400 MHz)
6
1
2
PhH); R : 3.75 (s, 3H, 4´-OCH ); R : 7.30–7.55 (m, 4H, PhH); IR (KBr):
3
δ 1.66–-1.72 (m, 2H, 3a-H, 6a-H), 1.75–1.80 (m, 2H, 3b-H, 6b-H),
1
5
-1
1
648 (C=O), 1577 (C=C), 1362 (C–N) cm . Anal. calcd for C H ClNO :
30
32
3
.89–1.96 (m, 2H, 2a-H, 7a-H), 2.05–2.12 (m, 4H, 2b-H, 7b-H, 4a-H,
C, 73.53; H, 6.58; N, 2.86; found: C, 73.31; H, 6.50; N, 2.66%.
a-H), 2.26–2.32 (m,, 2H, 4b-H, 5b-H), 5.25 (s, 1H, 9-H), 6.96–7.18
9
- (3,4-Dimethoxyphenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-
1
2
(m, 4H, PhH); R : 2.17 (s, 3H, 4´-CH ); R :7.20–7.44 (m, 5H, PhH);
3
hexahydroacridine-1,8(2H,5H)-dione (3p): Yield 0.336 g (82%);
-1
IR (KBr): 1640 (C=O), 1573 (C=C), 1362 (C–N) cm . Anal. calcd
for C H NO : C, 81.43; H, 6.57; N, 3.65; found: C, 81.30; H, 6.44; N,
3
+
yellow powder; m.p. 256–258 ˚C; MS (ESI) m/z 410.2 [M+H] .
2
6
25
2
1
H NMR (DMSO-d , 400 MHz) δ 0.99 (s, 6H, -2CH ), 1.09 (s, 6H,
.54%.
0-(4-Chlorophenyl)-9-(p-tolyl)-3,4,6,7,9,10-hexahydroacridine-
,8(2H,5H)-dione (3i): Yield 0.334 g (81%); pale grey powder; m.p.
6
3
-
5
2CH ), 2.21–2.38 (m, 8H, 2a-H, 7a-H, 2b-H, 7b-H, 4a-H, 5a-H, 4b-H,
1
3
b-H), 5.04 (s, 1H, 9-H), 6.68–6.94 (m, 3H, PhH), 7.28 (br, 1H, 10-
1
1
1
+
1
NH); R : 3.78 (s, 3H, 4´-OCH ), 3.83 (s, 3H, 3´-OCH ); IR (KBr): 1640
90–192 ˚C; MS (ESI) m/z 418.2 [M+H] . H NMR (DMSO-d , 400
3
3
6
-1
(
7
C=O), 1582 (C=C), 1363 (C–N) cm . Anal. calcd for C H NO : C,
MHz) δ 1.67–1.73 (m, 2H, 3a-H, 6a-H), 1.76–1.82 (m, 2H, 3b-H, 6b-
H), 1.89–1.97 (m, 3H, 2a-H, 7a-H, 2b-H), 2.01–2.13 (m, 3H, 7b-H, 4a-
H, 5a-H), 2.24–2.31 (m, 2H, 4b-H, 5b-H), 5.23 (s, 1H, 9-H), 6.95–7.16
25 31 4
3.32; H, 7.63; N, 3.42; found: C, 73.13; H, 7.58; N, 3.31%.
- (3,4-Dimethoxyphenyl) -3,3,6,6-tetramethyl-10-phenyl-
3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione (3q): Yield
0.403 g (83%), yellow powder; m.p. 176–178 ˚C; MS (ESI) m/z 486.3
9
1
2
(m, 4H, PhH), R : 2.17 (s, 3H, 4´-CH ); R : 7.18–7.42 (m, 4H, PhH);
3
-1
IR (KBr): 1639 (C=O), 1571 (C=C), 1365 (C–N) cm . Anal. calcd for
C H ClNO : C, 74.72; H, 5.79; N, 3.35; found: C,74.59; H, 5.64; N,
3
+
1
[
(
M+H] . H NMR (DMSO-d , 400 MHz) δ 0.84 (s, 6H, -2CH ), 0.96
6
3
2
6
24
2
s, 6H, -2CH ), 1.80–1.84 (m, 2H, 2a-H, 7a-H), 2.06–2.12 (m, 2H, 2b-
.31%.
3
1
0-(Naphthalen-1-yl)-9-(p-tolyl)-3,4,6,7,9,10-hexahydroacridine-
H, 7b-H), 2.16–2.26 (m, 4H, 4a-H, 5a-H, 4b-H, 5b-H), 5.25 (s, 1H,
1
1
2
,8(2H,5H)-dione (3j): Yield 0.346 g (80%); dark brown powder; m.p.
52–254 ˚C; MS (ESI) m/z 434.3 [M+H] . H NMR (DMSO-d , 400
MHz) δ 1.53–1.59 (m, 2H, 3a-H, 6a-H), 1.66–1.72 (m, 2H, 3b-H, 6b-
H), 1.97–1.99 (m, 4H, 2a-H, 7a-H, 2b-H, 7b-H), 2.14–2.23 (m, 4H, 4a-
H, 5a-H, 4b-H, 5b-H), 5.18 (s, 1H, 9-H), 7.07–7.26 (m, 4H, PhH), R :
.22 (s, 3H, 4´-CH ); R : 7.58–8.17 (m, 7H, NaphH); IR (KBr): 1640
C=O), 1563 (C=C), 1354 (C–N)cm . Anal. calcd for C H NO : C,
3.11; H, 6.28; N, 3.23; found: C, 83.01; H, 6.15; N, 3.21%.
9-H), 6.77–7.09 (m, 3H, PhH); R : 3.83 (s, 3H, 4´-OCH ), 3.91 (s, 3H,
3
+
1
2
3´-OCH ); R : 7.22–7.58 (m, 5H, PhH); IR (KBr): 1640 (C=O), 1571
(C=C), 1361 (C–N) cm . Anal. calcd for C H NO : C, 76.67; H, 7.26;
6
3
-1
31 35 4
N, 2.88; found: C, 76.51; H, 7.19; N, 2.73%.
1
10- (4-Chlorophenyl) -9- (3,4-dimethoxyphenyl) -3,3,6,6-
tetramethyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione (3r):
Yield 0.416 g (80%); yellow powder; m.p. 220–222 ˚C; MS (ESI) m/z
2
2
(
8
3
-1
30 27 2
+
1
520.3 [M+H] . H NMR (DMSO-d , 400 MHz) δ 0.75 (s, 6H, -2CH ),
6
3
3
,3,6,6-Tetramethyl-9-phenyl-3,4,6,7,9,10-hexahydroacridine-
0.88 (s, 6H, -2CH ), 1.70–1.79 (m, 3H, 2a-H, 7a-H, 2b-H), 1.96–2.00
3
1
2
,8(2H,5H)-dione (3k): Yield 0.262 g (75%); pale yellow powder; m.p.
(m, 2H, 7b-H, 4a-H), 2.10–2.11 (m, 3H, 5a-H, 4b-H, 5b-H), 5.14 (s, 1H,
+
1
1
62–264 ˚C; MS (ESI) m/z 350.2 [M+H] . H NMR (DMSO-d , 400
9-H), 6.66–6.99 (m, 3H, PhH); R : 3.73 (s, 3H, 4´-OCH ), 3.80 (s, 3H,
6
3
2
MHz) δ 0.98 (s, 6H, -2CH ), 1.10 (s, 6H, -2CH ), 2.17–2.46 (m, 8H,
2
3´-OCH ); R :7.07–7.47 (m, 4H, PhH); IR (KBr): 1640 (C=O), 1571
3
3
3
a-H, 7a-H, 2b-H, 7b-H, 4a-H, 5a-H, 4b-H, 5b-H), 5.08 (s, 1H, 9-H),
-1
(
C=C), 1362 (C–N) cm . Anal. calcd for C H ClNO : C, 71.59; H,
31
34
4
7
.07–7.28 (m, 5H, PhH), 7.32 (m, 1H, 10-NH); IR (KBr): 1640 (C=O),
6
.59; N, 2.69; found: C, 71.33; H, 6.38; N, 2.51%.
-1
1582 (C=C), 1370 (C–N) cm . Anal. calcd for C H NO : C, 79.05; H,
2
3
27
2
7
.79; N, 4.01; found: C, 79.01; H, 7.65; N, 3.96%.
This work was supported by National Natural Science
Foundation of China for Young Scholars (grant no. 21201087),
Natural Science Foundation of Jiangsu Province (No.
BK20131244 and BK20130460), Jiangsu Overseas Research
and Training Program for University Prominent Young and
Middle–aged Teachers and Presidents, and a start-up grant from
Jiangsu University of Science and Technology, P. R. China.
3
,3,6,6-Tetramethyl-9,10-diphenyl-3,4,6,7,9,10-hexahydroacridine-
1,8(2H,5H)-dione (3l): Yield 0.293 g (69%); pale yellow powder; m.p.
+
1
220–222 ˚C; MS (ESI) m/z 426.2 [M+H] H NMR (DMSO-d , 400
.
6
MHz) δ 0.81 (s, 6H, -2CH ), 0.96 (s, 6H, -2CH ), 2.06–2.13 (m, 4H, 2a-H,
3
3
7a-H, 2b-H, 7b-H), 2.17–2.24 (m, 4H, 4a-H, 5a-H, 4b-H, 5b-H), 5.30 (s,
2
1H, 9-H), 7.24–7.28 (m, 5H, PhH); R : 7.44-7.59 (m, 5H, PhH); IR (KBr):
-1
1646 (C=O), 1575 (C=C), 1365 (C–N) cm . Anal. calcd for C H NO : C,
29 31 2
8
1. 85; H, 7.34; N, 3.29; found: C, 81.74; H, 7.17; N, 3.24%.
1
0-(4-Chlorophenyl)-3,3,6,6-tetramethyl-9-phenyl-3,4,6,7,9,10-
Paper 1503402 doi: 10.3184/174751915X14377428213215
Published online: 7 August 2015
hexahydro-acridine-1,8(2H,5H)-dione (3m): Yield 0.377 g (83%);
yellow powder; m.p. 288–290 ˚C; MS (ESI) m/z 460.3 [M+H] .
+