8050
W.-P. Mai et al. / Tetrahedron 71 (2015) 8041e8051
NMR (400 MHz, CDCl3)
d
: 7.93 (d, J¼8.0 Hz, 2H), 7.63 (t, J¼7.2 Hz,
J¼9.6 Hz, 1H), 4.75 (d, J¼9.2 Hz, 1H), 3.45 (s, 3H); 13C NMR
1H), 7.51 (t, J¼8.0 Hz, 2H), 7.41e7.27 (m, 4H), 7.19 (t, J¼8.8 Hz, 3H),
7.09 (t, J¼8.0 Hz, 0.8 Hz,1H), 6.98 (d, J¼7.2 Hz,1H), 4.97 (d, J¼6.0 Hz,
1H), 4.70 (d, J¼6.4 Hz, 1H), 4.40e4.27 (m, 2H), 2.85e2.75 (m, 2H);
(100 MHz, CDCl3) d: 194.2, 166.3, 140.0, 139.3, 138.8, 135.2, 132.2,
130.2, 130.0, 129.0, 128.4, 128.3, 127.2, 123.7, 121.5, 115.1, 55.3, 43.9,
30.1; HRMS (ESI) calcd for C23H17BrClNO2 [MþH]þ: 453.0131;
found: 453.0130.
13C NMR (100 MHz, CDCl3)
d: 195.1, 166.9, 139.7, 137.8, 135.9, 133.7,
129.7, 129.2, 128.9, 128.70, 128.65, 127.8, 127.7, 126.9, 124.3, 117.4,
114.4, 56.2, 45.0, 39.0, 15.9; FT-IR
n
/cmꢁ1 (KBr) 1689, 1670, 1597,
4.2.15. 3-(4-Fluorobenzoyl)-4-(4-fluorophenyl)-1-methyl-3,4-
dihydroquinolin-2(1H)-one (3hi). White solid (271 mg, 72%): mp
178e180 ꢀC; Rf¼0.61 (petroleum ether/ethyl acetate¼3:1); 1H NMR
1458, 1385, 760, 702; HRMS (ESI) calcd for C25H21N2O2 [MþH]þ:
381.1603; found: 381.1608.
(400 MHz, CDCl3) d: 7.93e7.97 (m, 2H), 7.33e7.37 (td, 1H), 7.18e7.11
4.2.10. 3-Benzoyl-1-benzyl-4-phenyl-3,4-dihydroquinolin-2(1H)-one
(m, 5H), 7.10e6.98 (m, 3H), 6.87 (d, J¼7.6 Hz, 1H), 4.87 (d, J¼9.2 Hz,
(3fa). White solid (342 mg, 88%): mp 116e118 ꢀC; 1H NMR
1H), 4.77 (d, J¼8.8 Hz, 1H), 3.46 (s, 3H); 13C NMR (100 MHz, CDCl3)
(400 MHz, CDCl3)
d
: 8.01 (d, J¼0.8 Hz, 2H), 7.99 (t, J¼2.0 Hz, 1H),
d: 193.9, 167.2, 166.5, 164.6, 163.2, 160.7, 139.3, 135.5, 133.3, 131.5,
7.63e7.50 (m, 3H), 7.49e7.27 (m, 6H), 7.26e7.20 (m, 2H), 7.19 (d,
J¼5.6 Hz, 3H), 7.04e6.97 (m, 3H), 5.44 (d, J¼16.0 Hz, 1H), 5.15 (d,
J¼16.4 Hz, 1H), 5.08 (d, J¼16.4 Hz, 1H), 4.73 (d, J¼5.6 Hz, 1H); 13C
129.9, 128.4, 127.6, 123.6, 115.9, 115.0, 55.6, 43.9, 30.0; HRMS (ESI)
calcd for C23H17F2NO2 [MþH]þ: 377.1227; found: 377.1225.
NMR (100 MHz, CDCl3)
d: 195.5, 166.7, 140.4, 139.0, 136.6, 136.1,
4.2.16. 4-(4-Fluorophenyl)-1-methyl-3-propionyl-3,4-
dihydroquinolin-2(1H)-one (3hj). Sticky pale yellow oil (202 mg,
65%): Rf¼0.64 (petroleum ether/ethyl acetate¼3:1); 1H NMR
133.6, 129.1, 129.1, 128.84, 128.80, 128.7, 128.6, 128.5, 128.3, 127.8,
127.5, 127.2, 126.79, 126.75, 126.7, 126.6, 123.7, 116.0, 56.8, 46.7,
45.2; FT-IR
n
/cmꢁ1 (KBr) 1685, 1666, 1597, 1493, 1458, 1381, 1323,
(400 MHz, CDCl3) d: 7.35e7.31 (m,1H), 7.13e7.09 (m, 3H), 7.07e7.00
752, 729, 698; HRMS (ESI) calcd for C29H23NO2 [MþH]þ: 418.1807;
(m, 3H), 6.94 (t, J¼3.2 Hz, 1H), 4.69 (d, J¼8.0 Hz, 1H), 3.95 (d,
found: 418.1798.
J¼8.0 Hz, 1H), 3.46 (t, J¼10.6 Hz, 3H), 2.62e2.54 (m, 1H), 2.48e2.40
(m, 1H), 1.00 (m, 3H); 13C NMR (100 MHz, CDCl3)
d: 205.4, 166.6,
4.2.11. 3-Acetyl-1-benzyl-4-phenyl-3,4-dihydroquinolin-2(1H)-one
163.1, 160.7, 139.1, 135.6, 129.7, 128.6, 128.2, 127.4, 123.7, 116.0, 115.0,
60.6, 42.9, 36.6, 29.8; HRMS (ESI) calcd for C19H18FNO2 [MþH]þ:
311.1322; found: 311.1320.
(3fg). White solid (256 mg, 67%): mp 150e152 ꢀC; 1H NMR
(400 MHz, CDCl3)
d: 7.35e7.25 (m, overlapping CDCl3, 7H),
7.23e7.17 (m, 2H), 7.13 (dd, J¼7.6 Hz, 1.6 Hz, 2H), 7.04e6.99 (m, 3H),
5.23 (td, J¼18.0 Hz, 4.0 Hz, 2H), 4.74 (d, J¼6.0 Hz, 1H), 4.13 (d,
4.2.17. 3-Benzoyl-1-benzyl-4-phenyl-3,4-dihydro-1,8-naphthyridin-
2(1H)-one (3ia). Pale yellow solid (280 mg, 62%): mp 155e158 ꢀC,
Rf¼0.54 (petroleum ether/ethyl acetate¼4:1); 1H NMR (400 MHz,
J¼6.4 Hz, 1H), 2.28 (s, 3H); 13C NMR (100 MHz, CDCl3)
d: 202.3,
166.5, 139.8, 138.5, 136.5, 129.2, 129.0, 128.8, 128.2, 127.9, 127.43,
127.35, 127.2, 126.82, 126.75, 126.4, 123.9, 115.9, 62.1, 46.5, 43.6,
CDCl3)
d
: 8.32 (dd, J¼4.8 Hz, 1.2 Hz, 1H), 7.96 (d, J¼8.0 Hz, 2H), 7.60
29.5; FT-IR
n
/cmꢁ1 (KBr) 1720, 1666, 1597, 1493, 1458, 1381, 756,
(t, J¼7.2 Hz, 1H), 7.48 (q, J¼6.8 Hz, 4H), 7.27e7.29 (m, overlapping
CDCl3, 4H), 7.23e7.25 (m, 5H), 7.07e7.10 (m, 2H), 6.95 (dd, J¼7.2 Hz,
J¼4.8 Hz, 1H), 5.53 (dd, J¼19.2 Hz, 14.4 Hz, 2H), 5.02 (d, J¼7.6 Hz,
694; HRMS (ESI) calcd for C24H21NO2[MþH]þ: 356.1651; found:
356.1657.
1H), 4.70 (d, J¼7.6 Hz, 1H); 13C NMR (100 MHz, CDCl3)
d: 195.0,
4.2.12. 3-Benzoyl-4-(4-methoxyphenyl)-1-methyl-3,4-
dihydroquinolin-2(1H)-one (3ga). White solid (264 mg, 76%): mp
166.7, 150.6, 146.7, 139.5, 137.7, 136.8, 136.3, 133.6, 129.2, 128.9,
128.7, 128.6, 128.2, 128.0, 127.7, 127.1, 122.6, 119.1, 55.9, 44.1, 43.6;
132e133 ꢀC; 1H NMR (400 MHz, CDCl3)
d
: 8.01 (dt, J¼5.6 Hz, 1.6 Hz,
FT-IR n
/cmꢁ1 (KBr) 1689, 1666, 1585, 1442, 1377, 1319, 1211, 733,
2H), 7.59e7.54 (m, 1H), 7.47e7.43 (td, J¼7.2 Hz, 1.6 Hz, 2H), 7.35 (t,
J¼1.2 Hz, 1H), 7.13 (dd, J¼7.6 Hz, 2.0 Hz, 3H), 7.04 (td, J¼7.6 Hz,
0.8 Hz, 1H), 6.90 (d, J¼7.6 Hz, 1H), 6.85 (dd, J¼6.4 Hz, 2.0 Hz, 2H),
4.93 (d, J¼8.4 Hz, 1H), 4.71 (d, J¼8.0 Hz, 1H), 3.78 (s, 3H), 3.47 (s,
690; HRMS (ESI) calcd for C28H23N2O2 [MþH]þ: 419.1760; found:
419.1762.
4.2.18. 3-(4-Methoxybenzoyl)-1-methyl-4-phenyl-3,4-
dihydroquinolin-2(1H)-one (3ak). Sticky pale yellow oil (301 mg,
81%): Rf¼0.44 (petroleum ether/ethyl acetate¼3:1); 1H NMR
3H); 13C NMR (100 MHz, CDCl3)
d: 195.8, 166.9, 158.8, 139.5, 136.8,
133.3,131.9, 129.2,128.7, 128.7, 128.6,128.1, 127.9, 123.5, 114.9,114.4,
55.9, 55.2, 44.1, 29.9; FT-IR
n
/cmꢁ1 (KBr) 1693,1658, 1597, 1512,
(400 MHz, CDCl3) d: 7.97e7.93 (m, 2H), 7.26e7.19 (m, 3H), 7.13 (d,
1462, 1373, 1246, 1034, 752; HRMS (ESI) calcd for C24H21NO3
J¼8.4 Hz, 1H), 7.04 (td, J¼0.8 Hz, 1H), 6.95e6.91 (m, 3H), 4.93 (d,
[MþH]þ: 372.1600; found: 372.1609.
J¼7.6 Hz, 1H), 4.73 (d, J¼7.2 Hz, 1H), 3.87 (s, 3H), 3.47 (s, 3H); 13C
NMR (100 MHz, CDCl3) d: 193.8, 166.8, 163.8, 140.3, 139.5, 131.2,
4.2.13. 3-Benzoyl-4-(3,4-dimethoxyphenyl)-1-methyl-3,4-
dihydroquinolin-2(1H)-one (3ha). White solid (253 mg, 55%): mp
129.5, 129.0, 128.7, 128.1, 128.0, 127.5, 127.4, 123.5, 114.9, 113.9, 55.6,
55.5, 44.9, 30.0; HRMS (ESI) calcd for C24H21NO3 [MþH]þ: 371.1521;
found: 371.1520.
166e167 ꢀC; 1H NMR (400 MHz, CDCl3)
d
: 7.93 (dd, J¼7.2 Hz, 1.2 Hz,
2H), 7.58e7.54 (m, 1H), 7.47 (td, J¼7.2 Hz, 1.6 Hz, 2H), 7.36e7.32 (m,
1H), 7.13 (d, J¼4.0 Hz, 1H), 7.05 (td, J¼7.2 Hz, 0.8 Hz, 1H), 6.90 (d,
J¼7.6 Hz, 1H),6.81e6.69 (m, 3H), 4.96 (d, J¼9.2 Hz, 1H), 4.72 (d,
J¼8.8 Hz, 1H), 3.85 (s, 3H), 3.77 (s, 3H), 3.47 (s, 3H); 13C NMR
4.2.19. 4-(3-Bromophenyl)-1-methyl-3-(4-methylbenzoyl)-3,4-
dihydroquinolin-2(1H)-one (3jc). White solid (390 mg, 90%): mp
160e162 ꢀC; Rf¼0.51 (petroleum ether/ethyl acetate¼3:1); 1H NMR
(100 MHz, CDCl3)
d: 195.9, 167.1, 149.2, 148.3, 139.4, 137.0, 133.3,
(400 MHz, CDCl3)
d
: 7.85e7.83 (d, J¼8.4 Hz, 2H), 7.39e7.33 (m, 3H),
132.1, 128.6, 128.5, 128.1, 123.5, 120.6, 114.9, 111.6, 111.3, 55.8, 55.5,
7.27 (d, J¼8.4 Hz, 2H), 7.19e7.11 (m, 3H), 7.06 (td, J¼0.8 Hz, 1H), 6.89
(d, J¼7.6 Hz, 1H), 4.90 (d, J¼7.6 Hz, 1H), 4.71 (d, J¼8.0 Hz, 1H), 3.46
44.4, 29.9, 29.7; FT-IR
n
/cmꢁ1 (KBr) 1689, 1662, 1597, 1516, 1458,
1365, 1265, 1142, 1026, 764; HRMS (ESI) calcd for
(s, 3H), 2.42 (s, 3H); 13C NMR (100 MHz, CDCl3)
d: 194.7,166.4,144.5,
C
25H23NO4[MþH]þ: 402.1705; found: 402.1712.
142.6, 139.5, 133.9, 131.3, 130.6, 129.5, 128.9, 128.6, 128.4, 126.7,
123.6, 123.0, 115.1, 55.5, 44.5, 30.0, 21.7; HRMS (ESI) calcd for
4.2.14. 4-(4-Bromophenyl)-3-(4-chlorobenzoyl)-1-methyl-3,4-
dihydroquinolin-2(1H)-one (3db). White solid (362 mg, 80%): mp
202e204 ꢀC; Rf¼0.60 (petroleum ether/ethyl acetate¼3:1); 1H NMR
C
24H20BrNO2 [MþH]þ: 433.0677; found: 433.0675.
4.2.20. 3-(2-Chlorobenzoyl)-4-(2-chlorophenyl)-1-methylquinolin-
2(1H)-one (4kl). White solid (244 mg, 60%): mp 222e225 ꢀC;
Rf¼0.21 (petroleum ether/ethyl acetate¼3:1); 1H NMR (400 MHz,
(400 MHz, CDCl3) d: 7.84e7.87 (m, 2H), 7.41e7.46 (m, 4H), 7.35 (t,
J¼7.4 Hz, 1H), 7.02e7.12 (m, 4H), 6.84 (d, J¼7.6 Hz, 1H), 4.85 (d,