V. Beigi-Somar et al.
3
EtOAc 3/1, Rf = 0.38) afording 0.27 g (81%) 4b. Color-
s, OMe), 5.65 (1H, s, CH), 7.14 (1H, t, J = 7.2 Hz, CH),
3
3
̄
less oil; IR (KBr): V =3389, 3031, 2980, 1730, 1648, 1252,
7.19 (2H, d, J = 7.6 Hz, 2 CH), 7.29 (2H, t, J = 7.2 Hz,
2 CH), 7.33–7.37 (2H, m, 2 CH), 7.44 (1H, d, 3J=7.2 Hz,
CH), 7.72 (1H, s, CH), 13.08 (1H, br s, OH) ppm; 13C NMR
(125.7 MHz, CDCl3): δ=54.9 (OMe), 90.7 (C), 116.3 (CH),
119.7 (CH), 121.4 (C), 126.7 (CH), 127.9 (CH), 128.2 (CH),
129.1 (2 CH), 130.1 (2 CH), 131.8 (CH), 134.1 (C), 135.2
(C), 141.8 (C), 163.1 (C), 167.1 (CH), 188.5 (C) ppm;
EI-MS (70 eV): m/z (%)=401 ([M+2]+, 4), 399 (M+, 4),
342 (17), 266 (53), 250 (40), 155 (78), 77 (100).
1
1126 cm−1; H NMR (500.1 MHz, CDCl3): δ = 2.42 (3H,
s, Me), 3.68 (3H, s, OMe), 5.70 (1H, s, CH), 7.17 (2H, d,
3
3J = 7.4 Hz, 2 CH), 7.24 (2H, d, J = 7.8 Hz, 2 CH), 7.29
(2H, d, 3J=7.8 Hz, 2 CH), 7.30 (2H, t, 3J=7.7 Hz, 2 CH),
7.36 (1H, t, 3J=7.7 Hz, CH), 12.71 (1H, br s, OH) ppm; 13
C
NMR (125.7 MHz, CDCl3): δ=24.3 (Me), 55.2 (OMe), 90.2
(C), 116.3 (CH), 126.8 (CH), 127.2 (2 CH), 128.4 (2 CH),
129.5 (2 CH), 129.9 (2 CH), 134.3 (C), 135.7 (C), 138.1
(C), 141.7 (C), 162.4 (C), 165.1 (C), 187.8 (C) ppm; EI-MS
(70 eV): m/z (%)=335 (M+, 3), 278 (14), 202 (76), 111 (80),
91 (38), 77 (100).
Methyl 2‑hydroxy‑6‑oxo‑4‑phenyl‑1‑[3‑(trifluoromethyl)‑
phenyl]‑1,6‑ dihydropyridine ‑3‑ carbox ylate (4f,
C20H14F3NO4) The crude product was purifed by column
chromatography (SiO2, hexane/EtOAc 3/1, Rf = 0.12)
Methyl 2‑hydroxy‑1‑(4‑methoxyphenyl)‑6‑oxo‑4‑phe‑
nyl‑1,6‑dihydropyridine‑3‑carboxylate (4c, C20H17NO5) The
crude product was purified by column chromatography
(SiO2, hexane/EtOAc 3/1, Rf =0.36) afording 0.22 g (62%)
affording 0.35 g (89%) 4f. Pale yellow oil; IR (KBr):
V = 3374, 3027, 2972, 1730, 1651, 1248, 1126 cm−1; H
1
̄
NMR (500.1 MHz, CDCl3): δ = 3.72 (3H, s, OMe), 5.76
3
̄
4c. Colorless oil; IR (KBr): V = 3395, 3026, 2962, 1730,
(1H, s, CH), 7.18 (2H, d, J = 7.7 Hz, 2 CH), 7.26 (1H, t,
1648, 1252, 1126 cm−1; H NMR (500.1 MHz, CDCl3):
3J=7.1 Hz, CH), 7.28 (2H, t, 3J=7.7 Hz, 2 CH), 7.38 (1H,
t, 3J=7.7 Hz, CH), 7.44 (1H, d, 3J=7.1 Hz, CH), 7.49 (1H,
t, 3J=7.1 Hz, CH), 8.11 (1H, s, CH), 13.27 (1H, br s, OH)
ppm; 13C NMR (125.7 MHz, CDCl3): δ=55.3 (OMe), 88.2
1
δ=3.57 (3H, s, OMe), 3.70 (3H, s, OMe), 5.64 (1H, s, CH),
6.97 (2H, d, 3J=7.6 Hz, 2 CH), 7.18 (2H, d, 3J=7.3 Hz, 2
CH), 7.21 (2H, d, 3J=7.6 Hz, 2 CH), 7.31 (2H, t, 3J=7.3 Hz,
2 CH), 7.37 (1H, t, 3J=7.3 Hz, CH), 12.93 (1H, br s, OH)
ppm; 13C NMR (125.7 MHz, CDCl3): δ=53.9 (OMe), 55.9
(OMe), 89.2 (C), 114.1 (2 CH), 116.1 (CH), 126.9 (CH),
128.7 (2 CH), 129.3 (2 CH), 129.8 (2 CH), 132.3 (C), 135.1
(C), 142.6 (C), 159.7 (C), 161.2 (C), 165.9 (C), 189.2 (C)
ppm; EI-MS (70 eV): m/z (%)=351 (M+, 1), 294 (11), 218
(89), 110 (62), 107 (100), 77 (80).
3
(C), 116.1 (CH), 121.2 (CH, q, J = 5.7 Hz), 125.4 (CF3,
q, 1J=274.7 Hz), 126.3 (CH, q, 3J=5.6 Hz), 126.9 (CH),
2
128.8 (2 CH), 129.4 (2 CH), 131.1 (C, q, J = 30.2 Hz),
131.4 (CH), 132.6 (CH), 134.2 (C), 135.1 (C), 141.5 (C),
162.1 (C), 167.4 (C), 188.9 (C) ppm; EI-MS (70 eV): m/z
(%)=389 (M+, 1), 245 (16), 186 (45), 145 (24), 110 (84),
77 (100), 59 (46).
Methyl 1‑(4‑chlorophenyl)‑2‑hydroxy‑6‑oxo‑4‑phenyl‑1,6‑di‑
hydropyridine‑3‑carboxylate (4d, C19H14ClNO4) The crude
product was purifed by column chromatography (SiO2, hex-
ane/EtOAc 3/1, Rf =0.40) afording 0.31 g (87%) 4d. Color-
M e t h y l 2 ‑ h y d r o x y ‑ 1 ‑ [ 4 ‑ ( m e t h o x y c a r b o n y l ) ‑
phenyl]‑6‑oxo‑4‑phenyl‑1,6‑dihydropyridine‑3‑carboxylate
(4g, C21H17NO6) The crude product was purifed by column
chromatography (SiO2, hexane/EtOAc 4/1, Rf =0.21) aford-
̄
̄
less oil; IR (KBr): V =3381, 3035, 2953, 1727, 1642, 1264,
ing 0.24 g (64%) 4g. Colorless oil; IR (KBr): V = 3411,
1109 cm−1; H NMR (500.1 MHz, CDCl3): δ = 3.68 (3H,
3022, 2988, 1743, 1731, 1642, 1278, 1106 cm−1; 1H NMR
1
s, OMe), 5.69 (1H, s, CH), 7.18 (2H, d, 3J=7.2 Hz, 2 CH),
(500.1 MHz, CDCl3): δ = 3.60 (3H, s, OMe), 3.83 (3H, s,
3
7.31 (2H, t, 3J=7.2 Hz, 2 CH), 7.37 (1H, t, 3J=7.2 Hz, CH),
OMe), 5.67 (1H, s, CH), 7.18 (2H, d, J = 7.5 Hz, 2 CH),
7.42 (2H, d, J = 7.8 Hz, 2 CH), 7.48 (2H, d, J = 7.8 Hz,
2 CH), 13.36 (1H, br s, OH) ppm; 13C NMR (125.7 MHz,
CDCl3): δ=54.7 (OMe), 90.1 (C), 115.8 (CH), 126.6 (CH),
128.9 (2 CH), 129.6 (2 CH), 129.9 (2 CH), 131.3 (2 CH),
133.8 (C), 134.7 (C), 138.2 (C), 141.2 (C), 163.1 (C), 166.8
(C), 187.1 (C) ppm; EI-MS (70 eV): m/z (%)=355 (M+, 1),
298 (9), 222 (34), 190 (81), 111 (64), 77 (100).
7.27 (2H, d, 3J=7.7 Hz, 2 CH), 7.31 (2H, t, 3J=7.5 Hz, 2
CH), 7.38 (1H, t, 3J=7.5 Hz, CH), 7.92 (2H, d, 3J=7.7 Hz,
2 CH), 13.28 (1H, br s, OH) ppm; 13C NMR (125.7 MHz,
CDCl3): δ=53.1 (OMe), 54.4 (OMe), 93.9 (C), 116.7 (CH),
125.3 (2 CH), 126.4 (CH), 128.7 (2 CH), 129.6 (2 CH),
130.8 (C), 131.6 (2 CH), 134.1 (C), 141.6 (C), 142.9 (C),
162.5 (C), 166.2 (C), 167.3 (C), 188.7 (C) ppm; EI-MS
(70 eV): m/z (%)=379 (M+, 1), 322 (6), 264 (67), 188 (41),
156 (82), 110 (43), 77 (80).
3
3
Methyl 1‑(3‑bromophenyl)‑2‑hydroxy‑6‑oxo‑4‑phenyl‑1,6‑di‑
hydropyridine‑3‑carboxylate (4e, C19H14BrNO4) The crude
product was purifed by column chromatography (SiO2, hex-
ane/EtOAc 4/1, Rf =0.36) afording 0.32 g (80%) 4e. Yel-
Methyl 2‑hydroxy‑1‑(4‑nitrophenyl)‑6‑oxo‑4‑phenyl‑1,6‑di‑
hydropyridine‑3‑carboxylate (4h, C19H14N2O6) The crude
product was purifed by column chromatography (SiO2,
hexane/EtOAc 1/1, Rf = 0.34) afording 0.34 g (92%) 4h.
̄
low oil; IR (KBr): V =3395, 3031, 2955, 1731, 1640, 1281,
1
1089 cm−1; H NMR (500.1 MHz, CDCl3): δ = 3.67 (3H,
1 3