Molecules 2014, 19
814
77%), m.p. 243–245 °C; Rf (1:1 toluene–hexane) 0.72; νmax (ATR) 747, 809, 820, 1011, 1088, 1158,
1231, 1509, 1605, 2205 cm−1; δH (300 MHz, CDCl3) 7.24 (t, J = 8.7 Hz, 2H), 7.26 (t, J = 8.7 Hz, 2H),
7.43–7.51 (m, 3H), 7.74 (t, J = 8.7 Hz, 2H), 7.75–7.80 (m, 2H), 7.82 (t, J = 8.7 Hz, 2H), 8.12 (d,
J = 2.4 Hz, 1H), 8.48 (d, J = 2.4 Hz, 1H), 8.48–8.49 (m, 2H); δC (75 MHz, CDCl3) 85.7, 98.2, 114.9 (d,
2
3
2JCF = 21.3 Hz), 116.2 (d, JCF = 21.4 Hz), 121.2, 123.1, 124.4, 128.7, 128.8, 129.1 (d, JCF = 8.3 Hz),
129.9, 130.3, 132.4 (d, 3JCF = 8.3 Hz), 132.5, 133.6 (d, 4JCF = 3.4 Hz), 133.9, 135.8 (d, 4JCF = 3.4 Hz),
136.1, 136.9, 139.2, 139.7, 147.6, 153.1, 159.1, 162.8 (d, 1JCF = 246.2 Hz), 163.0 (d, 1JCF = 247.0 Hz);
m/z 529 (100, MH+); HRMS (ES): MH+, found 529.1282. C34H20N2F2 Cl+ requires 529.1283.
35
6,8-Bis(4-fluorophenyl)-2-(4-methoxyphenyl)-4-(phenylethynyl)quinazoline (6h). A mixture of 5d
(0.20 g, 0.42 mmol), 4-fluorophenylboronic acid (0.15 g, 1.07 mmol), PdCl2(PPh3)2 (0.015 g,
0.02 mmol), PCy3 (0.01 g, 0.04 mmol) and K2CO3 (0.12 g, 1.30 mmol) in dioxane-water (20 mL)
afforded 6h (0.18 g, 58%), m.p. 211–230 °C; Rf (1:1 toluene–hexane) 0.50; νmax (ATR) 684, 750, 810,
1028, 1157, 1227, 1252, 1507, 1537, 1605, 2203 cm−1; δH (300 MHz, CDCl3) 3.88 (s, 3H), 7.00 (d,
J = 8.7 Hz, 2H), 7.22 (d, J = 8.7 Hz, 2H), 7.25 (d, J = 8.7 Hz, 2H), 7.44–7.50 (m, 2H), 7.75–7.84 (m,
5H), 8.09 (d, J = 2.1 Hz, 1H); 8.48 (d, J = 2.1 Hz, 1H), 8.59 (dd, J = 2.4 and 7.5 Hz, 2H); δC (75 MHz,
2
2
CDCl3) 55.4, 85.9, 97.7, 113.9, 114.9 (d, JCF = 21.4 Hz), 116.1 (d, JCF = 21.4 Hz), 121.4, 123.2,
124.2, 128.7, 129.1 (d, 3JCF = 8.3 Hz), 130.1, 130.3, 131.8, 132.5 132.6 (d, 3JCF = 8.4 Hz), 133.7, 133.8
4
4
(d, JCF = 3.0 Hz), 136.1 (d, JCF = 3.0 Hz), 138.5, 139.5, 147.9, 153.0, 160.0, 161.9, 162.8 (d,
1JCF = 245.9 Hz), 162.9 (d, 1JCF = 246.5 Hz); m/z 525 (100, MH+); HRMS (ES): MH+, found 525.1785.
+
C35H23N2OF2 requires 525.1778.
6,8-Bis(4-methoxyphenyl)-2-phenyl-4-(phenylethynyl)quinazoline (6i). A mixture of 5a (0.30 g,
0.64 mmol), 4-methoxyphenylboronic acid (0.20 g, 1.60 mmol), PdCl2(PPh3)2 (0.022 g, 0.03 mmol),
PCy3 (0.02 g, 0.06 mmol) and K2CO3 (0.23 g, 1.60 mmol) in dioxane-water (20 mL) afforded 6i
(0.23 g, 69%), m.p. 209–211 °C; Rf (2:1 toluene–hexane) 0.28; νmax (ATR) 691; 831, 1032, 1174,
1243, 1393, 1460, 1510, 1608, 2209 cm−1; δH (300 MHz, CDCl3) 3.88 (s, 3H), 3.93 (s, 3H), 7.07 (d,
J = 8.7 Hz, 2H), 7.11 (d, J = 8.7 Hz, 2H), 7.44–7.50 (m, 6H), 7.73 (d, J = 8.7 Hz, 2H), 7.77–7.81 (m,
2H), 7.86 (d, J = 8.7 Hz, 2H), 8.17 (d, J = 2.1 Hz, 1H); 8.48 (d, J = 2.1 Hz, 1H), 8.59 (dd, J = 2.4 and
7.5 Hz, 2H); δC (75 MHz, CDCl3) 55.3 (2×C), 86.1, 97.5, 113.4, 114.5, 121.4, 121.7, 124.6, 126.4
(2×C), 128.6 (2×C), 130.0, 130.3, 130.4, 132.1, 132.2, 132.5, 133.4, 137.8, 139.5, 140.0, 147.6, 152.7,
+
159.4, 159.5, 159.7; m/z 519 (100, MH+); HRMS (ES): MH+, found 519.2071. C36H27N2O2 requires
519.2073.
2-(4-Fluorophenyl)-6,8-bis(4-methoxyphenyl)-4-(phenylethynyl)quinazoline (6j). A mixture of 5b
(0.40 g, 0.86 mmol), 4-methoxyphenylboronic acid (0.26 g, 2.15 mmol), PdCl2(PPh3)2 (0.03 g,
0.04 mmol), PCy3 (0.024 g, 0.08 mmol) and K2CO3 (0.30 g, 2.15 mmol) in dioxane-water (30 mL)
afforded 6j (0.29 g, 62%), m.p. 236–238 °C; Rf (2:1 toluene–hexane) 0.33; νmax (ATR) 831, 1017,
1150, 1222, 1287, 1508, 1605, 2208 cm−1; δH (300 MHz, CDCl3) 3.89 (s, 3H), 3.94 (s, 3H), 7.07 (d,
J = 8.7 Hz, 2H), 7.11 (d, J = 8.7 Hz, 2H), 7.15 (d, J = 8.7 Hz, 2H), 7.44–7.49 (m, 3H), 7.73 (d,
J = 8.7 Hz, 2H), 7.75–7.80 (m, 2H), 7.83 (d, J = 8.7 Hz, 2H), 8.14 (d, J = 2.4 Hz, 1H), 8.46 (d,
J = 1.8 Hz, 1H), 8.57 (t, J = 8.7 Hz, 2H); δC (75 MHz, CDCl3) 55.3, 55.4, 86.0, 97.8, 113.5, 114.6,