J IRAN CHEM SOC
1
68–170 °C). IR (KBr): ν = 3369, 3213, 3114, 2963,
(t, J = 7.2 Hz, 3H, OCH CH ), 2.49 (s, 3H, 6-CH ), ABX-
2 3
2
3
3
−1
1
694, 1633, 1492, 1377, 1287, 1200, 1085, 1024 cm .
system, δ = 2.86 (dd, J = 16.7 Hz, J = 1.0 Hz, 1H),
B
AB
BX
1
2 3
H NMR (400 MHz, CDCl ): δ = 1.20 (t, J = 7.0 Hz, 3H,
δ = 3.12 (dd, J = 16.7 Hz, J = 8.8 Hz, 1H), 3.99
3
A
AB
AX
3
OCH CH ), 2.42 (s, 3H, 6-CH ), ABX-system, δ = 2.72
(m, 2H, OCH CH ), δ = 4.76 (brd, J = 8.8 Hz, 1H),
2
3
3
B
2
3
X
AX
2
3
(
(
dd, J = 16.6 Hz, J = 1.4 Hz, 1H), δ = 2.95
7.29–7.31 (m, 1H, aromatic H), 7.38–7.42 (m, 1H, aro-
matic H), 7.50–7.54 (m, 1H, aromatic H), 7.86–7.89 (m,
1H, aromatic H), 8.29 ppm (brd s, 1H, NH). UV (CHCl3):
AB
BX
A
2
3
dd, J = 16.6 Hz, J = 7.9 Hz, 1H), 4.13 (m, 2H,
AB
AX
3
OCH CH ), δ = 4.28 (brd d, J = 7.9 Hz, 1H), 7.23–
2
3
X
AX
7
.31 (m, 5H, aromatic H), 8.24 ppm (brd s, 1H, NH). UV
λ
(log ε) = 270 nm (4.04).
max
(
CHCl ): λ (log ε) = 265 nm (3.86).
Ethyl
6-methyl-4-(3-nitrophenyl)-2-oxo-1,2,3,4-tet-
3
max
Ethyl
4-(2-methoxyphenyl)-6-methyl-2-oxo-1,2,3,4-
rahydropyridine-5-carboxylate (1f) M. p. 162–164 °C, (Lit.
[26] 168–170 °C). IR (KBr): ν = 3375, 3232, 3203, 3132,
2982, 2906, 2868, 2777, 1697, 1630, 1582, 1529, 1497,
tetrahydropyridine-5-carboxylate (1b) M. p. 183–185 °C.
IR (KBr): ν = 3362, 3215, 3114, 2940, 2838, 1704, 1681,
−1
1
−1
1
643, 1488, 1461, 1365, 1287, 1219, 1028 cm .
H
1430, 1367, 1349, 1309, 1279, 1197, 1159, 1083 cm .
1
NMR (400 MHz, CDCl ): δ = 1.16 (t, J = 7.2 Hz, 3H,
H NMR (400 MHz, CDCl ): δ = 1.21 (t, J = 7.2 Hz, 3H,
3
3
OCH CH ), 2.44 (s, 3H, 6-CH ), ABX-system, δ = 2.73
OCH CH ), 2.47 (s, 3H, 6-CH ), ABX-system, δ = 2.72
2
3
3
B
2
3
3
B
2
3
2
3
(
dd, J = 16.7 Hz, J = 1.0 Hz, 1H), δ = 2.85 (dd,
(dd, J = 16.8 Hz, J = 0.8 Hz, 1H), δ = 3.03
AB
BX
A
AB
BX
A
2
3
2 3
JAB = 16.7 Hz, J = 8.2 Hz, 1H), 3.85 (s, 3H, OCH ),
(dd, J = 16.8 Hz, J = 8.0 Hz, 1H), 4.15 (m, 2H,
AX
3
AB
AX
3
3
4
.08 (m, 2H, OCH CH ), δ = 4.61 (brd d, J = 8.2 Hz,
OCH CH ), δ = 4.38 (brd d, J = 8.0 Hz, 1H), 7.47–
2
3
X
AX
2
3
X
AX
1
H), 6.82–6.88 (m, 2H, aromatic H), 6.98–7.01 (m, 1H,
7.56 (m, 2H, aromatic H), 8.07–8.13 (m, 2H, aromatic
aromatic H), 7.19–7.23 (m, 1H, aromatic H), 7.96 ppm (brd
H), 8.22 ppm (brd s, 1H, NH). UV (CHCl ): λ
(log
3
max
s, 1H, NH). UV (CHCl ): λ (log ε) = 261 nm (3.98).
ε) = 270 nm (4.21).
3
max
Ethyl
4-(3-methoxyphenyl)-6-methyl-2-oxo-1,2,3,4-
Ethyl
6-methyl-4-(4-nitrophenyl)-2-oxo-1,2,3,4-tet-
tetrahydropyridine-5-carboxylate (1c) M. p. 156–159 °C.
IR (KBr): ν = 3355, 3217, 3132, 2935, 2883, 2741, 1696,
rahydropyridine-5-carboxylate (1g) M. p. 128–131 °C,
(Lit. [27] 132–133 °C). IR (KBr): ν = 3369, 3219, 2979,
2951, 2903, 2762, 1699, 1624, 1520, 1485, 1420, 1377,
1
1
628, 1598, 1492, 1460, 1428, 1368, 1329, 1279, 1199,
−
1
1
−1
1
087, 1039 cm . H NMR (400 MHz, CDCl ): δ = 1.22
1343, 1278, 1201, 1084, 1019 cm . H NMR (400 MHz,
3
(
t, J = 7.1 Hz, 3H, OCH CH ), 2.42 (s, 3H, 6-CH ), ABX-
CDCl ): δ = 1.20 (t, J = 7.2 Hz, 3H, OCH CH ), 2.46 (s,
2
3
3
3
2
3
2
3
2
system, δ = 2.72 (dd, J = 16.5 Hz, J = 1.1 Hz, 1H),
3H, 6-CH ), ABX-system, δ = 2.71 (dd, J = 16.7 Hz,
B
AB
BX
3
B
AB
2
3
3
3
2
δ = 2.94 (dd, J = 16.5 Hz, J = 7.7 Hz, 1H), 3.79
J
= 1.2 Hz, 1H), δ = 3.02 (dd, J = 16.7 Hz,
A
AB
AX
BX
A
AB
(
s, 3H, OCH ), 4.13 (m, 2H, OCH CH ), δ = 4.26 (brd d,
JAX = 8.0 Hz, 1H), 4.15 (m, 2H, OCH CH ), δ = 4.38
3
2
3
X
2
3
X
3
3
J
= 7.7 Hz, 1H), 6.75–6.81 (m, 3H, aromatic H), 7.22
(brd d, J = 8.0 Hz, 1H), 7.38 (d, J = 8.8 Hz, 2H, aro-
AX
AX
(
t, J = 7.8 Hz, 1H, aromatic H), 7.38 ppm (brd s, 1H, NH).
matic H), 8.17 (d, J = 8.8 Hz, 2H, aromatic H), 8.01 ppm
UV (CHCl ): λ (log ε) = 265 nm (3.93).
(brd s, 1H, NH). UV (CHCl ): λ
(log ε) = 272 nm
3
max
3
max
Ethyl
4-(4-methoxyphenyl)-6-methyl-2-oxo-1,2,3,4-
(4.22).
tetrahydropyridine-5-carboxylate (1d) M. p. 114–116 °C.
IR (KBr): ν = 3369, 3216, 3115, 2959, 2910, 2834, 1690,
Ethyl
4-(4-chlorophenyl)-6-methyl-2-oxo-1,2,3,4-tet-
rahydropyridine-5-carboxylate (1h) M. p. 155–157 °C,
(Lit. [26] 178–179 °C). IR (KBr): ν = 3365, 3234, 3137,
2976, 2894, 2766, 1691, 1627, 1490, 1409, 1378, 1317,
1
1
629, 1511, 1488, 1463, 1377, 1277, 1248, 1192, 1080,
−
1
1
035 cm . H NMR (400 MHz, CDCl ): δ = 1.22 (t,
3
−1
1
J = 7.1 Hz, 3H, OCH CH ), 2.41 (s, 3H, 6-CH ), ABX-
1283, 1197, 1087, 1015 cm . H NMR (400 MHz,
2
3
3
2
3
system, δ = 2.69 (dd, J = 16.4 Hz, J = 0.8 Hz, 1H),
CDCl ): δ = 1.21 (t, J = 7.0 Hz, 3H, OCH CH ), 2.42 (s,
B
AB
BX
3
2
3
2
3
2
δ = 2.92 (dd, J = 16.4 Hz, J = 7.7 Hz, 1H), 3.79
3H, 6-CH ), ABX-system, δ = 2.67 (dd, J = 16.6 Hz,
A
AB
AX
3
B
AB
3
3
2
(
s, 3H, OCH ), 4.14 (m, 2H, OCH CH ), δ = 4.23 (brd
J
= 1.2 Hz, 1H), δ = 2.95 (dd, J = 16.6 Hz,
3
2
3
X
BX
A
AB
3
d, J = 7.7 Hz, 1H), 6.82 (d, J = 8.7 Hz, 2H, aromatic
JAX = 7.8 Hz, 1H), 4.13 (m, 2H, OCH CH ), δ = 4.25
AX
2
3
X
3
H), 7.12 (d, J = 8.7 Hz, 2H, aromatic H), 8.09 ppm (brd s,
(brd d, J = 7.8 Hz, 1H), 7.13 (d, J = 8.6 Hz, 2H, aro-
AX
1
3
1
3
1
H, NH). C NMR (100 MHz, CDCl ): δ = 14.22, 19.18,
matic H), 7.26 (d, J = 8.6 Hz, 2H, aromatic H), 8.20 ppm
3
7.06, 38.20, 55.23, 60.22, 107.77, 114.08, 127.74, 134.20,
(brd s, 1H, NH). UV (CHCl ): λ
(log ε) = 277 nm
3
max
45.59, 158.49, 166.93, 170.99. UV (CHCl ): λ
(log
(3.94).
3
max
ε) = 256 (4.07).
Ethyl 6-methyl-4-(2-nitrophenyl)-2-oxo-1,2,3,4-tet-
rahydropyridine-5-carboxylate (1e) M. p. 199–201 °C, (Lit.
General procedure for oxidation of 5-carboethoxy-
2-oxo-1,2,3,4-tetrahydropyridines (1a–1h) to their cor-
responding
5-carboethoxy-2-oxo-1,2-dihydropyridines
[
2
1
26] 201–202 °C). IR (KBr): ν = 3374, 3221, 3132, 2986,
(2a–2h) Potassium peroxydisulfate (62 mg, 0.23 mmol)
was added to a solution of THPYs (0.23 mmol) in 10 ml
acetonitrile and water (7.5 + 2.5 ml). The reaction mixture
910, 2769, 1700, 1689, 1522, 1493, 1446, 1353, 1282,
−1 1
202, 1090 cm . H NMR (400 MHz, CDCl ): δ = 1.04
3
1
3