Vol. 25, No. 2, 2014
Fernández-Galleguillos et al.
369
(400 MHz, CDCl3) d 9.00 (m, 1H, quinoline), 7.88 (m,
2H, phenyl), 7.51 (m, 3H, phenyl), 7.10 (s, 1H, isoxazol),
7.05 (d, 1H, J 8.8 Hz, quinoline), 6.82 (dd, 1H, J 8.8,
1.5 Hz, quinoline), 4.05 (s, 3H, quinoline-OCH3),
3.97 (s, 3H, quinoline-OCH3); 13C NMR (100 MHz,
CDCl3) d 170.1 (C-isoxazol), 160.6 (C-isoxazol), 148.9
(C-quinoline), 148.3 (C-quinoline), 147.9 (C-quinoline),
139.7 (C-quinoline), 135.2 (CH-quinoline), 130.3
(C-quinoline), 129.0 (CH-phenyl), 127.1 (CH-phenyl),
125.8 (CH-phenyl), 122.3 (C-phenyl), 120.1 (C-quinoline),
109.6 (CH-quinoline), 104.9 (CH-quinoline), 100.9
(CH-isoxazol), 56.1 (OCH3-quinoline), 55.8 (OCH3-
quinoline); (QTOF-MS) m/z calculated for C20H15ClN2O3:
366.08; found: 366.78.
J 2.0 Hz, quinoline), 7.96 (m, 1H, quinoline), 7.90 (d,
2H, J 2.0 Hz, phenyl), 7.88 (s, 1H, quinoline), 7.54 (m,
3H, phenyl), 7.11 (s, 1H, isoxazol); 13C NMR (100 MHz,
CDCl3) d 170.3 (C-isoxazol), 160.4 (C-isoxazol), 148.0
(C-quinoline), 147.8 (C-quinoline), 139.7 (CH-quinoline),
131.6 (CH-quinoline), 130.4 (C-quinoline), 129.0
(CH-phenyl), 128.3 (CH-quinoline), 128.0 (CH-phenyl),
127.7 (CH-quinoline), 127.1 (C-quinoline), 126.7
(C-phenyl), 125.8 (CH-phenyl), 122.8 (C-quinoline),
100.8 (CH-isoxazol); (QTOF-MS) m/z calculated for
C18H10BrClN2O: 383.97; found: 384.30.
3-(2-Chloro-6-methoxyquinolin-3-yl)-5-phenylisoxazole (3h)
Yield: 77% as a white solid; m.p. 166-168 oC; IR (KBr)
1
ν
max/cm-1 2914, 1595, 1569, 821; H NMR (400 MHz,
3-(2-Chloro-6-fluoroquinolin-3-yl)-5-phenylisoxazole (3e)
CDCl3) d 8.54 (s, 1H, quinoline), 7.98 (d, 1H, J 9.3 Hz,
quinoline), 7.90 (dd, 2H, J 7.9, 1.3 Hz, phenyl), 7.52
(m, 3H, phenyl), 7.47 (dd, 1H, J 9.0, 2.7 Hz, quinoline),
7.16 (d, 1H, J 2.7 Hz, quinoline), 7.12 (s, 1H, isoxazol),
3.97 (s, 3H, quinoline-OCH3); 13C NMR (100 MHz,
CDCl3) d 170.2 (C-isoxazol), 160.5 (C-isoxazol), 158.5
(C-quinoline), 145.3 (C-quinoline), 143.9 (C-quinoline),
138.3 (CH-quinoline), 130.4 (C-quinoline), 129.7
(C-quinoline), 129.0 (CH-phenyl), 127.8 (CH-quinoline),
127.1 (CH-phenyl), 125.8 (CH-phenyl), 124.4 (C-phenyl),
122.8 (CH-quinoline), 105.2 (CH-quinoline), 100.9
(CH-isoxazol), 55.6 (OCH3-quinoline); (QTOF-MS) m/z
calculated for C19H13ClN2O2: 336.07; found: 336.81.
o
Yield: 61% as a white solid; m.p. 199-201 C;
1
IR (KBr) νmax/cm-1 2920, 1595, 1572, 825; H NMR
(400 MHz, CDCl3) d 8.59 (s, 1H, quinoline), 8.09 (dd,
1H, J 9.3, 4.9 Hz, quinoline), 7.89 (dd, 2H, J 7.8, 1.5 Hz,
phenyl), 7.59 (m, 1H, quinoline), 7.55 (d, 1H, J 2.9 Hz,
quinoline), 7.51 (m, 3H, phenyl), 7.11 (s, 1H, isoxazol);
13C NMR (100 MHz, CDCl3) d 170.6 (C-isoxazol), 160.0
(C-isoxazol), 148.5 (C-quinoline), 146.4 (C-quinoline),
138.6 (C-quinoline), 135.1 (CH-quinoline), 130.6
(CH-quinoline), 130.0 (C-quinoline), 130.0 (CH-phenyl),
129.1 (CH-phenyl), 127.8 (C-quinoline), 127.0 (C-phenyl),
125.9 (CH-phenyl), 123.9 (CH-quinoline), 121.7
(CH-quinoline), 100.8 (CH-isoxazol); (QTOF-MS) m/z
calculated for C18H10ClFN2O: 324.05; found: 324.57.
3-(2-Chloro-6-iodoquinolin-3-yl)-5-phenylisoxazole (3i)
Yield: 70% as a white solid; m.p. 196-198 oC; IR (KBr)
1
3-(2-Chloroquinolin-3-yl)-5-phenylisoxazole (3f)
ν
max/cm-1 2914, 1586, 1569, 825; H NMR (400 MHz,
Yield: 79% as a white solid; m.p. 150-152 oC; IR (KBr)
CDCl3) d 8.51 (s, 1H, quinoline), 8.30 (d, 1H, J 1.5 Hz,
quinoline), 8.05 (dd, 1H, J 8.8, 2.0 Hz, quinoline), 7.88
(dd, 2H, J 7.6, 1.7 Hz, phenyl), 7.80 (d, 1H, J 9.3 Hz,
quinoline), 7.53 (m, 3H, phenyl), 7.1 (s, 1H, isoxazol);
13C NMR (100 MHz, CDCl3) d 170.5 (C-isoxazol), 160.0
(C-isoxazol), 148.6 (C-quinoline), 146.7 (C-quinoline),
140.3 (CH-quinoline), 138.3 (CH-quinoline),
136.6 (CH-quinoline), 130.5 (C-quinoline), 129.9
(CH-quinoline), 129.1 (CH-phenyl), 128.2 (C-quinoline),
127.0 (CH-phenyl), 125.9 (CH-phenyl), 123.7 (C-phenyl),
100.8 (CH-isoxazol), 93.3 (C-quinoline); (QTOF-MS) m/z
calculated for C18H10ClIN2O: 431.95; found: 432.58.
1
ν
max/cm-1 2914, 1598, 1572, 820; H NMR (400 MHz,
CDCl3) d 8.65 (s, 1H, quinoline), 8.10 (d, 1H, J 8.3 Hz,
quinoline), 7.94 (d, 1H, J 8.6 Hz, quinoline), 7.90 (dd, 2H,
J 7.9, 1.6 Hz, phenyl), 7.84 (m, 1H, quinoline), 7.65 (m,
1H, quinoline), 7.53 (m, 3H, phenyl), 7.12 (s, 1H, isoxazol);
13C NMR (100 MHz, CDCl3) d 170.5 (C-isoxazol), 160.1
(C-isoxazol), 144.8 (C-quinoline), 139.0 (C-quinoline),
138.9 (CH-quinoline), 131.0 (CH-quinoline), 130.9
(C-quinoline), 130.5 (C-quinoline), 129.1 (CH-phenyl),
127.0 (CH-quinoline), 125.9 (CH-phenyl), 122.0
(CH-quinoline), 121.7 (CH-phenyl), 111.3 (CH-quinoline),
111.1 (C-phenyl), 100.8 (CH-isoxazol); (QTOF-MS) m/z
calculated for C18H11ClN2O: 306.06; found: 306.71.
3-(2-Chloro-5,7-dimethylquinolin-3-yl)-5-phenylisoxazole
(3j)
3-(6-Bromo-2-chloroquinolin-3-yl)-5-phenylisoxazole (3g)
Yield: 85% as a white solid; m.p. 182-184 oC; IR (KBr)
o
1
Yield: 64% as a white solid; m.p. 212-214 C;
ν
max/cm-1 2917, 1592, 1575, 823; H NMR (400 MHz,
1
IR (KBr) νmax/cm-1 2920, 1588, 1569, 825; H NMR
CDCl3) d 8.71 (s, 1H, quinoline), 7.89 (m, 2H, phenyl),
(400 MHz, CDCl3) d 8.55 (s, 1H, quinoline), 8.09 (d, 1H,
7.7 (s, 1H, quinoline), 7.51 (m, 3H, phenyl), 7.29 (s, 1H,