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3H), 2.94 (dd, J = 16.3, 6.8 Hz, 1H), 2.81 (dd, J = 16.3, 8.2 Hz, 1H);
13C NMR (100 MHz, CDCl3) δ 187.7, 159.7, 152.9, 135.8, 134.6,
131.3, 130.2, 129.0, 128.8, 128.4, 128.3, 127.7, 114.5, 110.0, 60.3, 57.5,
55.3, 44.3; FTIR (KBr, cm−1) 3030, 2928, 2836, 1634, 1598, 1511,
1440, 1372, 1294, 1251, 1178, 1124, 1032, 837, 735, 698; HRMS (ESI,
TOF) m/e calcd for [M + H]+ C25H23ClNO2 404.1417, found
404.1411.
2H), 4.58 (t, J = 7.1 Hz, 1H), 4.52 (d, J = 15.1 Hz, 1H), 4.30 (d, J =
15.1 Hz, 1H), 3.81 (s, 3H), 3.00 (dd, J = 16.3, 7.1 Hz, 1H), 2.81 (dd, J
= 16.3, 7.1 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ 187.3, 159.8,
153.8, 144.9, 143.4, 135.2, 129.7, 129.2, 128.6, 128.2, 127.7, 126.8,
123.6, 114.6, 108.4, 60.0, 58.0, 55.3, 44.1; FTIR (KBr, cm−1) 3031,
2914, 2837, 1638, 1578, 1510, 1443, 1329, 1251, 1179, 1107, 1031,
854, 735, 698; HRMS (ESI, TOF) m/e calcd for [M + H]+
C25H23N2O4 415.1658, found 415.1651.
1-Benzyl-2-(4-methoxyphenyl)-5-(4-nitrophenyl)-2,3-dihy-
dropyridin-4(1H)-one (3n). Compound 3n was prepared by the
general procedure described above, and 62 mg (78%) was isolated as
yellow oil: Rf 0.43 (hexanes/EtOAc, 1:1); 1H NMR (400 MHz,
CDCl3) δ 7.65 (s, 1H), 7.62−7.54 (m, 4H), 7.42−7.32 (m, 3H),
7.19−7.15 (m, 4H), 6.92−6.85 (m, 2H), 4.56 (t, J = 7.2 Hz, 1H), 4.48
(d, J = 15.1 Hz, 1H), 4.28 (d, J = 15.1 Hz, 1H), 3.81 (s, 3H), 2.98 (dd,
J = 16.3, 7.0 Hz, 1H), 2.81 (dd, J = 16.3, 7.4 Hz, 1H); 13C NMR (100
MHz, CDCl3) δ 187.3, 159.8, 153.4, 141.1, 135.3, 132.0, 129.8, 129.2,
128.6, 128.2, 127.7, 127.2, 119.6, 114.6, 108.9, 108.3, 60.1, 57.9, 55.4,
44.2; FTIR (KBr, cm−1) 3032, 2932, 2837, 2221, 1634, 1575, 1512,
1443, 1353, 1253, 1179, 1123, 1032, 962, 844, 735, 700; HRMS (ESI,
TOF) m/e calcd for [M + H]+ C26H23N2O2 395.1760, found
395.1751.
1-Benzyl-5-(4-bromophenyl)-2-(4-methoxyphenyl)-2,3-dihy-
dropyridin-4(1H)-one (3i). Compound 3i was prepared by the
general procedure described above, and 77 mg (86%) was isolated as
yellow oil: Rf 0.60 (hexanes/EtOAc, 1:1); 1H NMR (400 MHz,
CDCl3) δ 7.56−7.47 (m, 1H), 7.45−7.38 (m, 2H), 7.37−7.29 (m,
5H), 7.20−7.11 (m, 4H), 6.89−6.82 (m, 2H), 4.50 (t, J = 7.5 Hz, 1H),
4.40 (d, J = 15.1 Hz, 1H), 4.20 (d, J = 15.1 Hz, 1H), 3.79 (s, 3H), 2.92
(dd, J = 16.3, 6.9 Hz, 1H), 2.78 (dd, J = 16.3, 8.1 Hz, 1H); 13C NMR
(100 MHz, CDCl3) δ 187.6, 159.7, 152.9, 135.7, 135.0, 131.2, 130.2,
129.1, 129.0, 128.3, 127.7, 119.3, 114.5, 110.0, 60.3, 57.5, 55.3, 44.3;
FTIR (KBr, cm−1) 3030, 2932, 2835, 1634, 1596, 1511, 1440, 1356,
1294, 1252, 1178, 1123, 1032, 836, 811, 735, 698; HRMS (ESI, TOF)
m/e calcd for [M + H]+ C25H23BrNO2 448.0912, found 448.0898.
1-Benzyl-2-(4-methoxyphenyl)-5-(4-(trifluoromethyl)-
phenyl)-2,3-dihydropyridin-4(1H)-one (3j). Compound 3j was
prepared by the general procedure described above, and 70 mg (80%)
4-(1-Benzyl-6-(4-methoxyphenyl)-4-oxo-1,4,5,6-tetrahydro-
pyridin-3-yl)benzaldehyde (3o). Compound 3o was prepared by
the general procedure described above, and 66 mg (83%) was isolated
1
was isolated as yellow oil: Rf 0.55 (hexanes/EtOAc, 1:1); H NMR
(400 MHz, CDCl3) δ 7.60 (s, 1H), 7.59−7.53 (m, 4H), 7.43−7.30 (m,
3H), 7.21−7.14 (m, 4H), 6.92−6.85 (m, 2H), 4.55 (t, J = 7.4 Hz, 1H),
4.45 (d, J = 15.1 Hz, 1H), 4.25 (d, J = 15.1 Hz, 1H), 3.81 (s, 3H), 2.97
(dd, J = 16.3, 6.9 Hz, 1H), 2.82 (dd, J = 16.3, 7.8 Hz, 1H); 13C NMR
(100 MHz, CDCl3) δ 187.5, 159.8, 153.3, 139.8, 135.6, 130.1, 129.1,
128.5, 128.3, 127.7, 127.4 (q, J = 32.2 Hz), 127.3, 125.1 (q, J = 3.8
Hz), 124.5 (q, J = 272 Hz), 114.5, 109.6, 60.2, 57.7, 55.3, 44.3; 19F
NMR (376 MHz, CDCl3) δ 62.8; FTIR (KBr, cm−1) 3032, 2934,
2838, 1639, 1596, 1512, 1443, 1374, 1325, 1253, 1161, 1112, 1067,
847, 736, 699; HRMS (ESI, TOF) m/e calcd for [M + H]+
C26H23F3NO2: 438.1681, found 438.1692
4-(1-Benzyl-6-(4-methoxyphenyl)-4-oxo-1,4,5,6-tetrahydro-
pyridin-3-yl)benzamide (3k). Compound 3k was prepared by the
general procedure described above, and 61 mg (74%) was isolated as a
light yellow solid (mp 194−197 °C): Rf 0.47 (EtOAc); 1H NMR (400
MHz, DMSO) δ 8.24 (s, 1H), 7.85 (s, 1H), 7.78 (d, J = 8.5 Hz, 2H),
7.60 (d, J = 8.5 Hz, 2H), 7.42−7.35 (m, 2H), 7.35−7.29 (m, 3H), 7.24
(d, J = 8.7 Hz, 2H), 7.21 (s, 1H), 6.92 (d, J = 8.7 Hz, 2H), 4.86 (d, J =
15.2 Hz, 1H), 4.64 (dd, J = 7.0, 4.9 Hz, 1H), 4.23 (d, J = 15.2 Hz, 1H),
3.73 (s, 3H), 2.96 (dd, J = 16.0, 7.3 Hz, 1H), 2.54 (dd, J = 16.0, 4.8
Hz, 1H); 13C NMR (100 MHz, DMSO) δ 186.1, 167.8, 158.8, 154.3,
139.7, 136.9, 130.0, 129.9, 128.7, 127.8, 127.8, 127.6, 127.1, 125.7,
114.2, 107.3, 58.4, 56.8, 55.1, 43.9; FTIR (KBr, cm−1) 3346, 3194,
2925, 1669, 1594, 1511, 1378, 1250, 1027, 820, 774, 734, 699; HRMS
(ESI, TOF) m/e calcd for [M + H]+ C26H25N2O3 413.1865, found
413.1860.
4-(1-Benzyl-6-(4-methoxyphenyl)-4-oxo-1,4,5,6-tetrahydro-
pyridin-3-yl)benzamide (3l). Compound 3l was prepared by the
general procedure described above, and 67 mg (82%) was isolated as
yellow oil: Rf 0.41 (hexanes/EtOAc, 1:1); 1H NMR (400 MHz,
CDCl3) δ 7.95−7.87 (m, 2H), 7.68 (s, 1H), 7.61−7.56 (m, 2H),
7.41−7.32 (m, 3H), 7.22−7.12 (m, 4H), 6.91−6.84 (m, 2H), 4.55 (t, J
= 7.3 Hz, 1H), 4.48 (d, J = 15.1 Hz, 1H), 4.26 (d, J = 15.1 Hz, 1H),
3.81 (s, 3H), 2.98 (dd, J = 16.2, 7.0 Hz, 1H), 2.81 (dd, J = 16.2, 7.6
Hz, 1H), 2.57 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 197.7, 187.5,
159.7, 153.5, 141.3, 135.5, 134.1, 130.0, 129.1, 128.5, 128.4, 128.3,
127.7, 126.8, 114.5, 109.6, 60.1, 57.8, 55.3, 44.3, 26.5; FTIR (KBr,
cm−1) 3032, 3003, 2961, 2837, 1673, 1634, 1591, 1512, 1442, 1358,
1269, 1180, 1124, 1032, 957, 844, 734, 700; HRMS (ESI, TOF) m/e
calcd for [M + H]+ C27H26NO3 412.1913, found 412.1913.
1-Benzyl-2-(4-methoxyphenyl)-5-(4-nitrophenyl)-2,3-dihy-
dropyridin-4(1H)-one (3m). Compound 3m was prepared by the
general procedure described above, and 75 mg (90%) was isolated as a
brown solid (mp 98−101 °C): Rf 0.45 (hexanes/EtOAc, 1:1); 1H
NMR (400 MHz, CDCl3) δ 8.15−8.11 (m, 2H), 7.75 (s, 1H), 7.67−
7.63 (m, 2H), 7.42−7.34 (m, 3H), 7.21−7.15 (m, 4H), 6.90−6.86 (m,
1
as yellow oil: Rf 0.36 (hexanes/EtOAc, 1:1); H NMR (400 MHz,
CDCl3) δ 9.94 (s, 1H), 7.85−7.76 (m, 2H), 7.71 (s, 1H), 7.68−7.65
(m, 2H), 7.42−7.32 (m, 3H), 7.22−7.13 (m, 4H), 6.92−6.85 (m, 2H),
4.56 (t, J = 7.2 Hz, 1H), 4.49 (d, J = 15.1 Hz, 1H), 4.28 (d, J = 15.1
Hz, 1H), 3.81 (s, 3H), 2.99 (dd, J = 16.2, 7.0 Hz, 1H), 2.82 (dd, J =
16.2, 7.3 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ 191.9, 187.4, 159.8,
153.6, 142.9, 135.4, 133.5, 129.9, 129.1, 128.5, 128.3, 127.7, 127.1,
114.5, 109.4, 60.1, 57.9, 55.3, 44.3; FTIR (KBr, cm−1) 3031, 2933,
2837, 1693, 1590, 1512, 1443, 1353, 1305, 1251, 1176, 1123, 1031,
833, 735, 700; HRMS (ESI, TOF) m/e calcd for [M + H]+
C26H24NO3 398.1756, found 398.1747.
1-Benzyl-2-(4-methoxyphenyl)-5-(naphthalen-2-yl)-2,3-di-
hydropyridin-4(1H)-one (3p). Compound 3p was prepared by the
general procedure described above, and 70 mg (83%) was isolated as
brown oil: Rf 0.43 (hexanes/EtOAc, 1:1); 1H NMR (400 MHz,
CDCl3) δ 7.89 (s, 1H), 7.79 (dd, J = 8.3, 5.8 Hz, 3H), 7.68−7.59 (m,
2H), 7.46−7.29 (m, 5H), 7.26−7.13 (m, 4H), 6.93−6.85 (m, 2H),
4.53 (t, J = 7.5 Hz, 1H), 4.43 (d, J = 15.2 Hz, 1H), 4.21 (d, J = 15.1
Hz, 1H), 3.80 (s, 3H), 2.98 (dd, J = 16.2, 6.8 Hz, 1H), 2.84 (dd, J =
16.2, 8.2 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ 188.0, 159.6, 153.4,
135.9, 133.8, 133.7, 131.9, 130.4, 129.0, 128.4, 128.3, 127.7, 127.7,
127.5, 127.5, 126.7, 125.7, 125.3, 125.0, 114.4, 111.0, 60.3, 57.5, 55.3,
44.5; FTIR (KBr, cm−1) 3054, 2960, 2836, 1635, 1592, 1511, 1441,
1360, 1303, 1251, 1178, 1107, 1032, 818, 734, 699; HRMS (ESI,
TOF) m/e calcd for [M + H]+ C29H26NO2 420.1964, found 420.1953.
1-Benzyl-2-(4-methoxyphenyl)-5-(thiophen-3-yl)-2,3-dihy-
dropyridin-4(1H)-one (3q). Compound 3q was prepared by the
general procedure described above, and 18 mg (24%) was isolated as
yellow oil: Rf 0.50 (hexanes/EtOAc, 1:1); 1H NMR (400 MHz,
CDCl3) δ 7.69 (s, 1H), 7.60 (dd, J = 3.0, 1.1 Hz, 1H), 7.39−7.31 (m,
3H), 7.27 (dd, J = 5.0, 3.0 Hz, 1H), 7.22 (dd, J = 5.0, 1.1 Hz, 1H),
7.20−7.14 (m, 4H), 6.90−6.84 (m, 2H), 4.50 (t, J = 7.5 Hz, 1H), 4.42
(d, J = 15.1 Hz, 1H), 4.21 (d, J = 15.1 Hz, 1H), 3.81 (s, 3H), 2.94 (dd,
J = 16.3, 6.9 Hz, 1H), 2.80 (dd, J = 16.3, 8.2 Hz, 1H); 13C NMR (100
MHz, CDCl3) δ 187.8, 159.6, 152.3, 135.9, 130.3, 129.0, 128.4, 128.3,
127.7, 125.6, 124.5, 118.9, 114.4, 106.9, 60.2, 57.5, 55.3, 44.3; FTIR
(KBr, cm−1) 3030, 2925, 2853, 1598, 1511, 1440, 1296, 1252, 1178,
1112, 1031, 838, 783, 734, 699; HRMS (ESI, TOF) m/e calcd for [M
+ H]+ C23H22NO2S 376.1371, found 376.1370.
1-Benzyl-5-(4-methoxyphenyl)-2,3-dihydropyridin-4(1H)-
one (5a). Compound 5a was prepared by the general procedure
described above, and 41 mg (70%) was isolated as yellow oil. Spectral
data of the title compound were identical to those in our previous
report.3a
9501
dx.doi.org/10.1021/jo301531k | J. Org. Chem. 2012, 77, 9496−9503