PAPER
Thiosalicylic Acid Catalyzed Multicomponent Reactions
3997
J = 8.8 Hz, 2 H, ArH), 7.28 (t, J = 7.2 Hz, 2 H, ArH), 6.66 (s, 1 H,
HRMS (ESI): m/z [M – H]+ calcd for C35H22BrN: 534.0852; found:
CH), 6.63 (s, 2 H, ArH), 3.54 (s, 3 H, CH3);
584.0874.
HRMS (ESI): m/z [M – H]+ calcd for C28H21NO: 386.1539; found:
386.1554.
17-(4-Tolyl)-8,17-dihydrodinaphtho[2,3-a:2¢,3¢-j]acridine (4k)
IR (KBr): 3390.7, 3048.2, 1620.5, 1493.7, 1460.3, 1251.5, 876.7,
736.7 cm–1.
1H NMR (400 MHz, DMSO-d6, 25 °C): d = 9.76 (s, 1 H, NH), 9.15
(s, 2 H, ArH), 8.45 (s, 2 H, ArH), 8.19 (d, J = 8.4 Hz, 2 H, ArH),
8.00 (d, J = 8.4 Hz, 2 H, ArH), 7.96 (d, J = 8.8 Hz, 2 H, ArH), 7.68
(d, J = 8.0 Hz, 2 H, ArH), 7.55–7.51 (m, 2 H, ArH), 7.44–7.41 (m,
4 H, ArH), 6.94 (s, 1 H, CH), 6.89 (d, J = 8.0 Hz, 2 H, ArH), 1.99
(s, 3 H, CH3).
14-(2,4-Dichlorophenyl)-7,14-dihydrodibenzo[a,j]acridine (4f)
IR (KBr): 3409.1, 3039.9, 1621.6, 1584.5, 1480.3, 1404.2, 1262.9,
1040.3, 810.7, 740.6 cm–1.
1H NMR (400 MHz, DMSO-d6, 25 °C): d = 9.65 (s, 1 H, NH), 8.55
(d, J = 8.8 Hz, 2 H, ArH), 7.80 (dd, J = 16.0, 17.2 Hz, 4 H, ArH),
7.55 (t, J = 8.0 Hz, 2 H, ArH), 7.34–7.31 (m, 4 H, ArH), 7.08 (s,
1 H, ArH), 7.02 (d, J = 5.2 Hz, 1 H, ArH), 6.98–6.97 (m, 1 H, ArH),
6.69–6.67 (m, 1 H, CH).
HRMS (ESI): m/z [M – H]+ calcd for C36H25N: 470.1903; found:
470.1906.
HRMS (ESI): m/z [M – H]+ calcd for C27H17Cl2N: 424.0654; found:
424.0664.
17-(4-Methoxyphenyl)-8,17-dihydrodinaphtho[2,3-a:2¢,3¢-
j]acridine (4l)
14-(3,4-Dimethoxyphenyl)-7,14-dihydrodibenzo[a,j]acridine
(4g)
IR (KBr): 3406.7, 3052.8, 1622.7, 1496.5, 1460.7, 1250.0, 1031.5,
869.4, 741.0 cm–1.
IR (KBr): 3350.4, 2996.6, 1588.3, 1529.2, 1510.6, 1467.8, 1401.8,
1264.7, 1141.2, 1024.8, 818.8, 742.0 cm–1.
1H NMR (400 MHz, DMSO-d6, 25 °C): d = 9.77 (s, 1 H, NH), 9.17
(s, 2 H, ArH), 8.45 (s, 2 H, ArH), 8.21 (d, J = 8.4 Hz, 2 H, ArH),
8.00 (d, J = 8.4 Hz, 2 H, ArH), 7.96 (d, J = 8.8 Hz, 2 H, ArH), 7.70
(d, J = 8.8 Hz, 2 H, ArH), 7.54 (t, J = 7.2 Hz, 2 H, ArH), 7.44–7.41
(m, 4 H, ArH), 6.95 (s, 1 H, CH), 6.65 (d, J = 8.8 Hz, 2 H, ArH).
HRMS (ESI): m/z [M – H]+ calcd for C36H25NO: 486.1852; found:
486.1874.
1H NMR (400 MHz, DMSO-d6, 25 °C): d = 9.52 (s, 1 H, NH), 8.58
(d, J = 8.4 Hz, 2 H, ArH), 7.78 (d, J = 8.0 Hz, 2 H, ArH), 7.74 (d,
J = 8.8 Hz, 2 H, ArH), 7.51 (t, J = 7.2 Hz, 2 H, ArH), 7.33 (d,
J = 8.4 Hz, 2 H, ArH), 7.28 (t, J = 7.2 Hz, 2 H, ArH), 7.04 (dd,
J1 = 8.4 Hz, J2 = 2.0 Hz, 1 H, ArH), 6.65 (d, J = 8.4 Hz, 2 H, ArH),
6.63 (s, 1 H, CH), 3.60 (s, 3 H, CH3), 3.53 (s, 3 H, CH3).
HRMS (ESI): m/z [M – H]+ calcd for C29H23NO2: 416.1645; found:
416.1669.
17-(2,4-Dichlorophenyl)-8,17-dihydrodinaphtho[2,3-a:2¢,3¢-
j]acridine (4m)
IR (KBr): 3402.6, 3018.6, 1624.7, 1496.7, 1307.1, 1250.6, 889.3,
14-(Benzo[d][1,3]dioxol-5-yl)-7,14-dihydrodibenzo[a,j]acridine
(4h)
874.4, 739.2 cm–1.
IR (KBr): 3406.0, 3020.6, 1587.9, 1530.5, 1484.6, 1246.2, 1033.7,
1H NMR (400 MHz, DMSO-d6, 25 °C): d = 10.05 (s, 1 H, NH), 9.15
(s, 1 H, ArH), 8.49 (s, 1 H, ArH), 8.14 (d, J = 8.4 Hz, 2 H, ArH),
8.04–8.01 (m, 4 H, ArH), 7.60–7.54 (m, 3 H, ArH), 7.48–7.45 (m,
5 H, ArH), 7.15 (dd, J = 8.8, 2.4 Hz, 1 H, ArH), 7.03 (m, 1 H, CH).
HRMS (ESI): m/z [M – H]+ calcd for C35H21Cl2N: 524.0967; found:
524.0967.
922.0, 807.1, 746.4 cm–1.
1H NMR (400 MHz, DMSO-d6, 25 °C): d = 9.54 (s, 1 H, NH), 8.56
(d, J = 8.4 Hz, 2 H, ArH), 7.79 (d, J = 8.0 Hz, 2 H, ArH), 7.75 (d,
J = 8.8 Hz, 2 H, ArH), 7.52 (t, J = 7.6 Hz, 2 H, ArH), 7.35 (d,
J = 8.4 Hz, 2 H, ArH), 7.29 (t, J = 7.2 Hz, 2 H, ArH), 7.12–7.08 (m,
2 H, ArH), 6.64 (d, J = 7.6 Hz, 2 H, ArH), 6.63 (s, 1 H, CH), 5.77
(s, 2 H, CH2).
17-(Thien-2-yl)-8,17-dihydrodinaphtho[2,3-a:2¢,3¢-j]acridine
(4n)
HRMS (ESI): m/z [M – H]+ calcd for C28H19NO2: 400.1332; found:
400.1364.
IR (KBr): 3379.1, 3057.9, 1584.0, 1525.8, 1462.2, 1396.6, 1263.7,
816.2, 750.0, 703.4 cm–1.
14-(Thiophen-2-yl)-7,14-dihydrodibenzo[a,j]acridine (4i)
IR (KBr): 3378.8, 3060.0, 1583.9, 1525.7, 1462.3, 1263.7, 816.2,
750.0, 703.4 cm–1.
1H NMR (400 MHz, DMSO-d6, 25 °C): d = 9.65 (s, 1 H, NH), 8.55
(d, J = 8.8 Hz, 2 H, ArH), 7.82 (d, J = 7.6 Hz, 2 H, ArH), 7.78 (d,
J = 8.8 Hz, 2 H, ArH), 7.55 (t, J = 8.0 Hz, 2 H, ArH), 7.34 (s, 1 H,
ArH), 7.32–7.31 (m, 3 H, ArH), 7.07 (s, 1 H, CH), 7.02 (d,
J = 5.2 Hz, 1 H, ArH), 6.98–6.97 (m, 1 H, ArH), 6.69–6.67 (m, 1 H,
ArH).
1H NMR (400 MHz, DMSO-d6, 25 °C): d = 9.91 (s, 1 H, NH), 9.19
(s, 2 H, ArH), 8.50 (s, 2 H, ArH), 8.22 (d, J = 8.4 Hz, 2 H, ArH),
8.05–8.00 (m, 4 H, ArH), 7.55 (t, J = 7.2 Hz, 2 H, ArH), 7.47–7.38
(m, 5 H, ArH), 7.21 (m, 1 H, ArH), 7.00 (d, J = 5.2 Hz, 1 H, ArH),
6.69 (dd, J = 4.8, 3.6 Hz, 1 H, ArH).
HRMS (ESI): m/z [M – H]+ calcd for C33H21NS: 462.1311; found:
462.1310.
Acknowledgment
HRMS (ESI): m/z [M – H]+ calcd for C25H17NS: 362.0998; found:
362.0978.
We are grateful for financial support from the NSFC (Nos.
21072163 and 21002083), the Graduate Foundation of Jiangsu Pro-
vince (No. CX09S_043Z), the Graduate Foundation of Xuzhou
Normal University (No. 09YLA005), the Science Foundation in In-
terdisciplinary Major Research Project of Xuzhou Normal Univer-
sity (No. 09XKXK01), the Natural Science Foundation
(09 KJB150011) and Qing Lan Project (08QLT001) of Jiangsu
Education Committee, and the Science & Technology Foundation
of Xuzhou Municipal Government (No. XM08C027).
17-(4-Bromophenyl)-8,17-dihydrodinaphtho[2,3-a:2¢,3¢-j]acri-
dine (4j)
IR (KBr): 3389.6, 3046.0, 1620.5, 1493.1, 1250.5, 1010.4, 880.3,
863.7 cm–1.
1H NMR (400 MHz, DMSO-d6, 25 °C): d = 9.84 (s, 1 H, NH), 9.15
(s, 2 H, ArH), 8.47 (s, 2 H, ArH), 8.20 (d, J = 8.4 Hz, 2 H, ArH),
8.00 (t, J = 9.2 Hz, 4 H, ArH), 7.77 (d, J = 8.8 Hz, 2 H, ArH), 7.57–
7.53 (m, 2 H, ArH), 7.46–7.42 (m, 4 H, ArH), 7.30 (d, J = 8.4 Hz,
2 H, ArH), 7.01 (s, 1 H, CH).
Synthesis 2010, No. 23, 3993–3998 © Thieme Stuttgart · New York