Molecules 2014, 19
9731
2
H), 7.73 (d, J 7.8 Hz, 2H), 7.85 (s, 1H), 7.94 (s, 1H), 8.13 (s, 1H), 8.22 (s, 1H), 12.18 (s, 1H); δ (75
C
MHz, DMSO-d
6
) 21.8, 28.2 (2 × C), 43.1, 46.2, 55.4, 55.5, 55.6, 55.7, 70.0, 113.6, 114.8 (2 × C),
1
15.0, 115.7, 121.7, 122.4, 124.1, 127.3, 128.1, 128.5, 129.1, 130.3, 130.5, 131.1, 131.9, 132.2 (2 × C),
32,7, 133.0, 137.5, 138.9, 142.9, 145.2, 155.6, 158.7, 159.0 (2 × C), 159.7, 162.6, 163.7; m/z 787
1
+
+
+
(
100, MH ); HRMS (ES): MH , found 787.3502. C H N O requires 787.3496.
49 47 4 6
2
-(3-(2-Methyl-6,8-diphenyl-4-oxo-1,2,3,4-tetrahydroquinazolin-2-yl)-2,2-dimethylpropyl)-6,8-
diphenylquinazolin-4(3H)-ones (4j). A mixture of 3d (0.50 g, 0.72 mmol), phenylboronic acid (0.40 g,
.25 mmol), PdCl (PPh ) (0.05 g, 0.07 mmol), PCy (0.04 g, 0.15 mmol) and K CO (0.40 g, 2.89 mmol)
3
2
3 2
3
2
3
−1
in dioxane-water (40 mL) afforded 4j as a solid (0.37 g, 76%), mp. 289–292 °C; νmax (neat) cm 3410,
194, 3055, 1688, 1627, 1601, 1518, 1495, 1465, 1385, 1260, 1213, 1029, 894, 788, 762, 698; δH
300 MHz, DMSO-d ) 0.89 (s, 3H), 1.02 (s, 3H), 1.11 (s, 3H) 1.55 (d, J 15.0 Hz, 1H), 2.10 (d, J 13.8 Hz,
3
(
6
1
1
H), 2.64 (d, J 15.3 Hz, 1H), 2.97 (d, J 13.5 Hz, 1H), 5.26 (s, 1H), 7.08 (t, J 7.8 Hz, 2H) 7.22–7.45 (m,
3H), 7.52 (t, J 7.5 Hz, 2H), 7.61 (d, J 7.8 Hz, 2H), 7.84 (d, J 7.8 Hz, 2H), 7.93 (d, J 6.0 Hz, 2H), 7.99
(
s, 1H), 8.36 (s, 1H) 12.27 (s, 1H); δ (75 MHz, DMSO-d ) 29.7, 29.9, 31.0, 35.0, 45.2, 46.6, 56.6,
C 6
7
1
1
0.6, 115.1, 122.4, 123.1, 125.1, 126.2, 127.0, 127.2, 127.4, 127.7, 127.8, 127.9, 128.1, 128.4, 129.0,
29.1, 129.4, 129.7, 130.6, 133.2, 134.1, 137.8, 139.3, 139.4, 139.8, 140.1, 142.9, 145.4, 156.1, 162.4,
+
+
+
62.8; m/z 681 (100, MH ); HRMS (ES): MH , found 681.3232. C H N O requires 681.3230.
4
6
41
4
2
2
6
4
0
7
1
3
-(3-(6,8-Bis(2(4-fluorophenyl))-2-methyl-4-oxo-1,2,3,4-tetrahydroquinazolin-2-yl)-2,2-dimethylpropyl)-
,8-bis(2-(4-fluorophenyl))quinazolin-4(3H)-one (4k). A mixture of 3d (0.50 g, 0.72 mmol),
-fluorophenylboronic acid (0.46 g, 3.25 mmol), PdCl
.15 mmol) and K CO (0.40 g, 2.89 mmol) in dioxane-water (40 mL) afforded 4k as a solid (0.42 g,
7%), mp. 303–305 °C; νmax (neat) cm 3387, 3181, 3048, 1688, 1653, 1608, 1507, 1466, 1381, 1222,
158, 1015, 825, 804, 791, 636, 565, 517; δ (300 MHz, DMSO-d ) 1.01 (s, 3H), 1.05 (s, 3H), 1.07 (s,
H) 1.59 (d, J 15.3 Hz, 1H), 2.06 (d, J 15.3 Hz, 1H), 2.67 (d, J 13.8 Hz, 1H), 2.85 (d,
2 3 2 3
(PPh ) (0.05 g, 0.07 mmol), PCy (0.04 g,
2
3
−1
H
6
J 15.3 Hz, 1H), 5.39 (s, 1H), 7.05 (t, J 9.0 Hz, 2H), 7.17 (t, J 9.0 Hz, 2H), 7.20 (t, J 9.0 Hz, 2H),
.30–7.39 (m, 5H), 7.50 (t, J 6.3 Hz, 2H), 7.62 (t, J 6.3 Hz, 2H), 7.85–7.88 (m, 3H), 7.93 (s, 1H), 8.02
7
(
br s, 1H), 8.32 (s, 1H), 12.27 (s, 1H); δ
C
2
(75 MHz, DMSO-d
6
) 29.7, 30.0, 30.9, 35.0, 45.4, 47.0, 70.5,
2
2
2
1
1
1
15.0, 115.2 (d, JCF 20.5 Hz), 116.0 (d, JCF 21.1 Hz), 116.1 (d, JCF 21.4 Hz), 116.4 (d, JCF 21.4 Hz),
3
3
3
22.3, 123.1, 125.0, 127.1, 128.0, 128.1 (d, JCF 8.0 Hz), 129.5 (d, JCF 8.0 Hz), 131.2 (d, JCF 8.3 Hz),
3
4
4
4
32.7 (d, JCF 8.0 Hz), 133.2, 134.0, 134.1 (d, JCF 3.2 Hz), 135.4 (d, JCF 3.2 Hz), 135.9 (d, JCF 2.9 Hz),
4
1
1
1
36.5 (d, JCF 2.9 Hz), 136.9, 138.5, 143.0, 145.3, 156.4, 161.8 (d, JCF 241.7 Hz), 162.0 (d,
1
1
+
J
CF 243.0 Hz), 162.1 (d, JCF 242.4 Hz), 162.6 (d, JCF 243.5 Hz), 162.3, 162.6; m/z 739 (100, MH );
+
+
35 4 2 4
HRMS (ES): MH , found 739.2709. C45H N O F requires 739.2696.
2-(3-(6,8-Bis(2-(4-methoxyphenyl))-2-methyl-4-oxo-1,2,3,4-tetrahydroquinazolin-2-yl)-2,2-dimethylpropyl)
-
6,8-bis(2-(4-methoxyphenyl))quinazolin-4(3H)-one (4l). A mixture of 3d (0.50 g,0.72 mmol),
4
0
8
1
-methoxyphenylboronic acid (0.49 g, 3.25 mmol), PdCl
2 3 2 3
(PPh ) (0.05 g, 0.07 mmol), PCy (0.04 g,
.15 mmol) and K CO (0.40 g, 2.89 mmol) in dioxane-water (40 mL) afforded 4l as a solid (0.47 g,
2
3
−1
1%), mp. 228–230 °C; νmax (neat) cm 3177, 3037, 2834, 1677, 1607, 1511, 1463, 1386, 1244, 1178,
034, 899, 827; δ (300 MHz, DMSO-d ) 0.93 (s, 3H), 1.03 (s, 3H), 1.08 (s, 3H) 1.57 (d,
H
6