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G. Bhargava et al. / Tetrahedron 64 (2008) 3017e3024
2.2.2.5. 5-[2-(6-Methoxy-2-phenyl-quinolin-4-yl)-vinyl]-6-methyl-
2,3-diphenyl-3H-pyrimidin-4-one 4e. Yellow solid, mp 195e
196 ꢂC; dH (CDCl3, 200 MHz): 2.7 (s, 3H, ePy CH3), 3.94
(s, 3H, eOCH3), 7.09 (d, J¼15.7 Hz, 1H, H8), 7.17e7.36
(m, 15H, aromatic), 7.86e7.91 (m, 3H, H13,14,16), 8.11 (s, 1H,
H10), 8.79 (d, J¼15.7 Hz, 1H, H7); dC (CDCl3, 75 MHz): 22.7,
55.8, 99.8, 114.3, 121.5, 122.8, 125.2, 127.3, 127.9, 128.0,
128.6, 128.9, 129.3, 129.4, 129.3, 130.2, 130.8, 131.5, 134.5,
137.3, 140.0, 144.1, 144.3, 144.7, 154.8, 156.3, 157.2, 160.8,
161.1; m/z 521 (Mþ); nmax (KBr)/cmꢁ11679, 1522, 1233,
1156. Anal. Calcd for C35H27N3O2: C, 80.59; H, 5.22; N,
8.06%. Found: C, 80.72; H, 5.36; N, 8.19%.
2.2.2.9. 5-[2-(6-Methoxy-2-phenyl-quinolin-4-yl)-vinyl]-6-mor-
pholin-4-yl-2,3-diphenyl-3H-pyrimidin-4-one 4i. Red solid,
mp 146e147 ꢂC; dH (CDCl3, 600 MHz): 3.75 (m, 4H, H, mor-
pholine), 3.84 (m, 4H, H, morpholine), 3.91 (s, 3H, eOCH3),
7.18 (d, J¼16.3 Hz, 1H, H8), 7.19e7.32 (m, 15H, aromatic),
7.35 (dd, J¼2.7, 9.0 Hz, 1H, H14), 7.41 (d, J¼2.7 Hz, 1H,
H16), 7.58 (d, J¼9.0 Hz, 1H, H13), 7.87 (s, 1H, H10), 8.49
(d, J¼16.3 Hz, 1H, H7); dC (150 MHz, CDCl3): 49.8 (eC mor-
pholine), 55.7 (eOCH3), 67.1 (eC morpholine), 99.2, 101.9,
114.1, 122.1, 124.6, 126.4, 127.3, 127.9, 128.4, 128.5, 128.9,
129.0, 129.0, 129.2, 129.9, 131.4, 134.6, 134.8, 137.5, 138.6,
144.5, 144.7, 153.5, 155.6, 157.7, 161.7, 162.7; m/z 592 (Mþ);
nmax (KBr)/cmꢁ1 1665, 1702, 1492, 1385. Anal. Calcd for
C38H32N4O3: C, 77.01; H, 5.44; N, 9.45%. Found: C, 77.19;
H, 5.56; N, 9.56%.
2.2.2.6. 5-{2-[6-Methoxy-2-(4-methoxy-phenyl)-quinolin-4-yl]-
vinyl}-6-methyl-2,3-diphenyl-3H-pyrimidin-4-one 4f. Yellow
solid, mp 194e195 ꢂC; dH (CDCl3, 200 MHz): 2.7 (s, 3H,
ePy CH3), 3.82 (s, 3H, eOCH3), 3.90 (s, 3H, eOCH3),
7.12 (d, J¼15.0 Hz, 1H, H8), 7.23e7.55 (m, 14H, aromatic),
7.87e7.94 (m, 3H, H13,14,16), 8.07 (s, 1H, H10), 8.93 (d, J¼
15.0 Hz, 1H, H7); dC (CDCl3, 75 MHz): 22.5, 54.7, 55.8,
100.2, 116.3, 121.3, 122.4, 125.6, 127.8, 127.3, 128.7, 128.9,
129.2, 129.5, 129.8, 130.2, 130.8, 131.1, 132.8, 134.3, 136.2,
136.8, 137.4, 146.1, 146.9, 155.0, 155.9, 159.6, 160.0, 160.4;
m/z 551 (Mþ); nmax (KBr)/cmꢁ1 1681, 1548, 1432, 1473,
1400, 1546. Anal. Calcd for C36H29N3O3: C, 78.38; H, 5.30;
N, 7.62%. Found: C, 78.49; H, 5.42; N, 7.51%.
2.2.2.10. 5-{2-[6-Methoxy-2-(4-methoxy-phenyl)-quinolin-4-yl]-
vinyl}-6-morpholin-4-yl-2,3-diphenyl-3H-pyrimidin-4-one 4j.
Fluorescent yellow solid, mp 203e204 ꢂC; dH (CDCl3,
600 MHz): 3.70 (m, 4H, morpholine), 3.89 (m, 4H, morpho-
line), 3.83 (s, 3H, eOCH3), 3.90 (s, 3H, OCH3), 7.16 (d,
J¼15.9 Hz, 1H, H8), 7.19e7.25 (m, 14H, aromatic), 7.27
(dd, J¼2.5, 9.2 Hz, 1H, H14), 7.53 (d, J¼2.5 Hz, 1H, H16),
7.59 (d, 1H, J¼9.2 Hz, H13), 8.15 (s, 1H, H10), 8.43 (d, 1H,
J¼15.9 Hz, H7); 13C NMR (75 MHz, CDCl3): d 49.4 (eC
morpholine), 55.0 (eOCH3), 55.3 (eOCH3), 67.2 (eC mor-
pholine), 99.3, 102.3, 122.1, 124.6, 126.4, 127.3, 128.0,
128.1, 128.3, 128.6, 128.9, 129.0, 129.0, 129.2, 129.9, 131.4,
134.6, 134.8, 137.5, 138.6, 144.5, 144.7, 153.5, 155.6, 157.2,
160.8, 162.1; m/z 622 (Mþ); nmax (KBr)/cmꢁ1 1663, 1583,
1510, 1430, 1133. Anal. Calcd for C39H34N4O4: C, 75.22;
H, 5.50; N, 9.00%. Found: C, 75.36; H, 5.63; N, 8.94%.
2.2.2.7. 5-{2-[2-(4-Chloro-phenyl)-6-methoxy-quinolin-4-yl]-
vinyl}-6-methyl-2,3-diphenyl-3H-pyrimidin-4-one 4g. Yellow
solid, mp 173e174 ꢂC; dH (CDCl3, 600 MHz): 2.7 (s, 3H,
ePy CH3), 3.94 (s, 3H, eOCH3), 7.20 (d, J¼15.71 Hz, 1H,
H8), 7.29e7.44 (m, 10H, aromatic), 7.80 (m, 2H, H14,16),
7.50 (d, J¼9.2 Hz, 2H, H20), 7.9 (s, 1H, H10), 8.05 (d, J¼
9.4 Hz, 1H, H13), 8.12 (d, J¼9.2 Hz, 2H, H19), 8.72 (d, J¼
15.7 Hz, 1H, H7); dC (CDCl3, 75 MHz): 22.7, 55.7, 102.0,
115.2, 118.2, 122.5, 126.7, 126.9, 128.1, 128.4, 128.6, 128.7,
128.8, 128.9, 129.1, 129.2, 129.9, 130.5, 131.7, 134.1, 135.3,
138.2, 146.5, 144.9, 153.2, 156.4, 157.8, 161.0, 161.2; m/z 555
(Mþ); nmax (KBr)/cmꢁ1 1675, 1619, 1531, 1235, 1211, 1129.
Anal. Calcd for C35H26ClN3O2: C, 75.60; H, 4.71; N, 7.56%.
Found: C, 75.77; H, 4.84; N, 7.68%.
2.2.2.11. 5-{2-[2-(4-Chloro-phenyl)-6-methoxy-quinolin-4-yl]-
vinyl}-6-morpholin-4-yl-2,3-diphenyl-3H-pyrimidin-4-one 4k.
Dark yellow solid, mp 158e159 ꢂC; dH (CDCl3, 600 MHz):
3.71e3.73 (m, 4H, morpholine), 3.81e3.83 (m, 4H, morpho-
line), 3.93 (s, 3H, eOCH3), 7.11 (d, 1H, J¼16.4 Hz, H8),
7.21e7.28 (m, 14H, aromatic), 7.30 (dd, J¼2.5, 9.1 Hz, 1H,
H14), 7.49 (d, J¼2.5 Hz, 1H, H16), 7.50 (d, J¼9.1 Hz, 1H,
H13), 7.92 (s, 1H, H10), 8.55 (d, J¼16.4 Hz, 1H, H7);
13C NMR (75 MHz, CDCl3): d 49.8 (C morpholine), 55.7
(eOCH3), 67.1 (C morpholine), 99.3, 102.3, 114.9, 122.1,
124.6, 126.4, 127.3, 128.0, 128.1, 128.3, 128.6, 129.0,
129.0, 129.2, 129.9, 131.4, 134.6, 134.8, 137.5, 138.6, 144.5,
144.7, 153.5, 155.6, 157.2, 160.8, 162.5; m/z 626 (Mþ); nmax
(KBr)/cmꢁ1 1650, 1620, 1581, 1544, 1488, 1417, 1232,
1120. Anal. Calcd for C38H31ClN4O3: C, 72.78; H, 4.98; Cl,
5.65; N, 8.93%. Found: C, 72.89; H, 5.12; N, 8.81%.
2.2.2.8. 5-[2-(8-Methoxy-2-phenyl-quinolin-4-yl)-vinyl]-6-methyl-
2,3-diphenyl-3H-pyrimidin-4-one 4h. Yellow solid, mp 179e
180 ꢂC; dH (CDCl3, 300 MHz): 2.7 (s, 3H, PyeCH3), 3.92 (s,
3H, eOCH3), 7.09 (d, J¼7.2 Hz, 1H, H14), 7.21 (d, J¼
15.3 Hz, 1H, H8), 7.22e7.43 (m, 15H, H, aromatic), 7.53 (un-
resolved d, J¼7.2 Hz, 1H, H15), 7.81 (d, J¼7.2 Hz, 1H, H16),
7.95 (s, 1H, H10), 8.92 (d, J¼15.3 Hz, 1H, H7); dC (CDCl3,
75 MHz): 22.7, 55.2, 107.2, 115.4, 115.9, 118.2, 126.2, 126.6,
127.7, 128.09, 128.7, 128.8, 129.1, 129.13, 129.2, 129.8,
130.2, 134.5, 137.3, 140.1, 140.7, 144.3, 144.8, 145.0, 155.7,
156.0, 153.6, 161.0, 161.1; m/z 521 (Mþ); nmax (KBr)/cmꢁ1
1684, 1643, 1548, 1506. Anal. Calcd for C35H27N3O2:
C, 80.59; H, 5.22; N, 8.06%. Found: C, 80.67; H, 5.39; N,
7.95%.
2.2.2.12.
5-[2-(8-Methoxy-2-phenyl-quinolin-4-yl)-vinyl]-6-
morpholin-4-yl-2,3-diphenyl-3H-pyrimidin-4-one 4l. Yellow
solid, mp 177e178 ꢂC; dH (CDCl3, 200 MHz): 3.73e3.74
(m, 4H, morpholine), 3.84e3.85 (m, 4H, morpholine), 3.94 (s,
3H, eOCH3), 7.13 (d, J¼7.8 Hz, 1H, H14), 7.28 (d, J¼
16.0 Hz, 1H, H8), 7.30e7.48 (m, 15H, aromatic), 7.53 (m,
1H, H15), 7.81 (d, J¼7.8 Hz, 1H, H16), 7.97 (s, 1H, H10),