Microwave-Assisted Multicomponent Reactions
Combinatorial Chemistry & High Throughput Screening, 2012, Vol. 15, No. 5 407
m/z calcd for C31H18Cl2NO2: 506.0710 [M+H]+, found:
506.0729.
8.69 (s, 1H, ArH), 8.53 (s, 1H, ArH), 8.47 (d, J = 8.0 Hz,
1H, ArH), 8.14-8.08 (m, 2H, ArH), 8.03-8.00 (m, 2H, ArH),
7.94-7.90 (m, 1H, ArH), 7.87 (d, J = 9.2 Hz, 1H, ArH), 7.69
(t, J = 7.6 Hz, 1H, ArH), 7.50-7.47 (m, 2H, ArH), 7.35 (d, J
= 8.4 Hz, 2H, ArH), 6.71 (d, J = 8.8 Hz, 2H, ArH), 6.16 (s,
1H, CH), 3.58 (s, 3H, CH3). HRMS (ESI): m/z calcd for
C32H22NO3: 468.1595 [M+H]+, found: 468.1611.
14-(4-Fluorophenyl)benzo[h]naphtho[2,3-a]acridine-15,16
(5H,14H)-dione (4q)
m.p.: >300oC; IR (KBr, ꢁ, cm-1): 3318, 3051, 1694, 1585,
1504, 1461, 1257, 1232, 889; 1H NMR (400MHz, DMSO-d6,
25oC): ꢀ = 10.54 (s, 1H, NH), 8.70 (s, 1H, ArH), 8.55 (s, 1H,
ArH), 8.49 (d, J = 8.0 Hz, 1H, ArH), 8.16-8.11 (m, 2H,
ArH), 8.05-8.01 (m, 2H, ArH), 7.93 (t, J = 7.2 Hz, 1H, ArH),
7.89 (d, J = 9.2 Hz, 1H, ArH), 7.71 (t, J = 7.6 Hz, 1H, ArH),
7.51-7.47 (m, 4H, ArH), 6.98 (t, J = 8.8 Hz, 2H, ArH), 6.23
(s, 1H, CH). HRMS (ESI): m/z calcd for C31H19FNO2:
456.1395 [M+H]+, found: 456.1416.
14-(4-(Dimethylamino)phenyl)benzo[h]naphtho[2,3-a]ac-
ridine-15,16(5H,14H)-dione (4v)
m.p.: 286-288oC; IR (KBr, ꢁ, cm-1): 3306, 3061, 1692,
1
1608, 1585, 1502, 1480, 1460, 1257, 874, 812, 738; H
NMR (400MHz, DMSO-d6, 25oC): ꢀ = 10.45 (s, 1H, NH),
8.69 (s, 1H, ArH), 8.53 (s, 1H, ArH), 8.46 (d, J = 8.0 Hz,
1H, ArH), 8.13-8.07 (m, 2H, ArH), 8.04-8.00 (m, 2H, ArH),
7.92 (t, J = 7.6 Hz, 1H, ArH), 7.85 (d, J = 9.2 Hz, 1H, ArH),
7.69 (t, J = 7.6 Hz, 1H, ArH), 7.51-7.45 (m, 2H, ArH), 7.24
(d, J = 8.8 Hz, 2H, ArH), 6.50 (d, J = 8.8 Hz, 2H, ArH), 6.09
(s, 1H, CH), 2.70 (s, 6H, CH3). HRMS (ESI): m/z calcd for
C33H25N2O2: 481.1911 [M+H]+, found: 481.1929.
14-(4-Bromophenyl)benzo[h]naphtho[2,3-a]acridine-15,16
(5H,14H)-dione (4r)
m.p.: >300oC; IR (KBr, ꢁ, cm-1): 3330, 2912, 1585, 1504,
1482, 1469, 1462, 1255, 1011, 911, 778; 1H NMR (400MHz,
DMSO-d6, 25oC): ꢀ = 10.56 (s, 1H, NH), 8.69 (s, 1H, ArH),
8.56 (s, 1H, ArH), 8.49 (d, J = 8.0 Hz, 1H, ArH), 8.16-8.12
(m, 2H, ArH), 8.05-8.01 (m, 2H, ArH), 7.94 (t, J = 7.2 Hz,
1H, ArH), 7.88 (d, J = 8.8 Hz, 1H, ArH), 7.71 (t, J = 7.2 Hz,
1H, ArH), 7.50-7.49 (m, 2H, ArH), 7.42 (d, J = 8.4 Hz, 2H,
ArH), 7.36 (d, J = 8.4 Hz, 2H, ArH), 6.20 (s, 1H, CH).
HRMS (ESI): m/z calcd for C31H19BrNO2: 516.0594
[M+H]+, found: 516.0611.
14-(3,4-Dimethoxyphenyl)benzo[h]naphtho[2,3-a]acridine- 15,
16(5H,14H)-dione (4w)
m.p.: 274-276oC; IR (KBr, ꢁ, cm-1): 3327, 3062, 2930,
1692, 1587, 1504, 1481, 1470, 1462, 1264, 1238, 1140,
1
1029, 871, 737; H NMR (400MHz, DMSO-d6, 25oC): ꢀ =
10.50 (s, 1H, NH), 8.76 (s, 1H, ArH), 8.54 (s, 1H, ArH),
8.47 (d, J = 7.6 Hz, 1H, ArH), 8.16 (d, J = 7.2 Hz, 1H, ArH),
8.10 (d, J = 8.8 Hz, 1H, ArH), 8.04-8.01 (m, 2H, ArH), 7.94-
7.91 (m, 1H, ArH), 7.87 (d, J = 8.8 Hz, 1H, ArH), 7.72-7.68
(m, 1H, ArH), 7.50-7.47 (m, 2H, ArH), 7.29 (d, J = 2.0 Hz,
1H, ArH), 6.74-6.67 (m, 2H, ArH), 6.53 (s, 1H, CH), 3.72 (s,
3H, CH3), 3.55 (s, 3H, CH3). HRMS (ESI): m/z calcd for
C33H24NO4: 498.1700 [M+H]+, found: 498.1721.
14-(4-Nitrophenyl)benzo[h]naphtho[2,3-a]acridine-15,16
(5H,14H)-dione (4s)
m.p.: >300oC; IR (KBr, ꢁ, cm-1): 3313, 3044, 1698, 1608,
1588, 1557, 1504, 1479, 1469, 1460, 1257, 877, 738, 631; 1H
NMR (400MHz, DMSO-d6, 25oC): ꢀ = 10.62 (s, 1H, NH),
8.70 (s, 1H, ArH), 8.56 (s, 1H, ArH), 8.51 (d, J = 7.6 Hz,
1H, ArH), 8.16-8.14 (m, 2H, ArH), 8.06-8.02 (m, 4H, ArH),
7.97-7.90 (m, 2H, ArH), 7.76 (d, J = 8.8 Hz, 2H, ArH), 7.72
(t, J = 7.6 Hz, 1H, ArH), 7.52-7.46 (m, 2H, ArH), 6.37 (s,
1H, CH). HRMS (ESI): m/z calcd for C31H19N2O4: 483.1340
[M+H]+, found: 483.1364.
14-(3,4,5-Trimethoxyphenyl)benzo[h]naphtho[2,3-a]acri-
dine-15,16(5H,14H)-dione (4x)
m.p.: 290-293oC; IR (KBr, ꢁ, cm-1): 3321, 3047, 1692,
1
1587, 1503, 1481, 1469, 1461, 1417, 1251, 1124, 871; H
NMR (400MHz, DMSO-d6, 25oC): ꢀ = 10.55 (s, 1H, NH),
8.82 (s, 1H, ArH), 8.55 (s, 1H, ArH), 8.48 (d, J = 8.0 Hz,
1H, ArH), 8.21 (d, J = 8.4 Hz, 1H, ArH), 8.11 (d, J = 9.2 Hz,
1H, ArH), 8.03 (m, 2H, ArH), 7.94-7.86 (m, 2H, ArH), 7.70
(t, J = 7.6 Hz, 1H, ArH), 7.53-7.46 (m, 2H, ArH), 6.77 (s,
2H, ArH), 6.18 (s, 1H, CH), 3.64 (s, 6H, CH3), 3.48 (s, 3H,
CH3). HRMS (ESI): m/z calcd for C34H26NO5: 528.1806
[M+H]+, found: 528.1819.
14-p-Tolylbenzo[h]naphtho[2,3-a]acridine-15,16(5H,14H)-
dione (4t)
m.p.: 292-294oC; IR (KBr, ꢁ, cm-1): 3335, 3048, 1585,
1
1504, 1481, 1470, 1461, 1424, 1255, 870, 737; H NMR
(400MHz, DMSO-d6, 25oC): ꢀ = 10.50 (s, 1H, NH), 8.68 (s,
1H, ArH), 8.54 (s, 1H, ArH), 8.47 (d, J = 8.0 Hz, 1H, ArH),
8.14-8.09 (m, 2H, ArH), 7.95-7.91 (m, 1H, ArH), 7.87 (d, J
= 8.8 Hz, 1H, ArH), 7.70 (t, J = 7.2 Hz, 1H, ArH), 7.50-7.47
(m, 2H, ArH), 7.33 (d, J = 8.0 Hz, 2H, ArH), 6.95 (d, J = 8.0
Hz, 2H, ArH), 6.17 (s, 1H, CH), 2.09 (s, 3H, CH3). HRMS
(ESI): m/z calcd for C32H22NO2: 452.1646 [M+H]+, found:
452.1671.
14-(Benzo[d][1,3]dioxol-5-yl)benzo[h]naphtho[2,3-a]acri-
dine-15,16(5H,14H)-dione (4y)
m.p.: >300oC; IR (KBr, ꢁ, cm-1): 3320, 3006, 2920, 1684,
1580, 1524, 1477, 1465, 1455, 1259, 1235, 1144, 1010, 872,
739; 1H NMR (400MHz, DMSO-d6, 25oC): ꢀ = 10.50 (s, 1H,
NH), 8.72 (s, 1H, ArH), 8.54 (s, 1H, ArH), 8.47 (d, J = 7.6
Hz, 1H, ArH), 8.17-8.15 (m, 1H, ArH), 8.12 (d, J = 9.2 Hz,
1H, ArH), 8.05-8.01 (m, 2H, ArH), 7.94-7.90 (m, 1H, ArH),
7.87 (d, J = 9.2 Hz, 1H, ArH), 7.70 (t, J = 7.6 Hz, 1H, ArH),
7.51-7.48 (m, 2H, ArH), 7.04 (d, J = 1.6 Hz, 1H, ArH), 6.86-
6.84 (m, 1H, ArH), 6.68 (d, J = 8.0 Hz, 1H, ArH), 6.15 (s,
14-(4-Methoxyphenyl)benzo[h]naphtho[2,3-a]acridine-15,
16(5H,14H)-dione (4u)
m.p.: 289-291oC; IR (KBr, ꢁ, cm-1): 3324, 1586, 1504,
1480, 1469, 1460, 1417, 1256, 1177, 1029, 870, 707; H
1
NMR (400MHz, DMSO-d6, 25oC): ꢀ = 10.49 (s, 1H, NH),