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YANKIN et al.
4C6H4), 9.99 s (1H, NH). Found, %: С 77.29; H 7.36;
N 4.81. C39H44N2O4. Calculated, %: С 77.45; H 7.33;
N 4.63.
(400 MHz, CDCl3), δ, ppm (J, Hz): 1.30 d [3H, OCH
(CH3)2, J 6.0], 1.36 d [3H, OCH(CH3)2, J 6.0], 2.77 d.d
(1H, C5HAHB, J 15.6, 12.0), 2.85 d.d (1H, C5HAHB, J
15.6, 4.4), 4.93 m [1H, OCH(CH3)2], 5.13–5.20 m (1H,
C6H), 6.21 s (1H, C2H), 6.71–7.41 m (16H, 2C6H5, 2-
thienyl), 10.67 s (1H, NH). 13С NMR spectrum (100
MHz, CDCl3), δС, ppm: 21.60, 36.47, 55.82, 58.93,
66.73, 98.90, 116.08, 118.79, 123.36, 123.45, 123.54,
124.07, 124.44, 125.94, 126.43, 128.17, 128.80,
138.05, 148.00, 149.65, 152.27, 156.27, 166.96.
Found, %: С 69.70; H 5.66; N 5.43. C29H28N2O2S2.
Calculated, %: С 69.57; H 5.64; N 5.59.
Methyl 2,6-di(2-thienyl)-1-phenyl-4-phenylamino-
1,2,5,6-tetrahydropyridine-3-carboxylate (Ij). Yield
3.82 g (81%), mp 171–172°C. IR spectrum, ν, cm–1:
1
3280 (NH), 1660 (C=O). Н NMR spectrum (400
MHz, DMSO-d6), δ, ppm (J, Hz): 2.77 d.d (1H,
C5HAHB, J 15.2, 12.0), 2.85 d.d (1H, C5HAHB, J 15.2,
4.0), 3.71 s (3Н, OCH3), 5.07–5.15 m (1H, C6H), 6.01
s (1H, C2H), 6.70–7.48 m (16H, 2C6H5, 2-thienyl),
10.44 s (1H, NH). Found, %: С 68.51; H 5.15; N 5.86.
C27H24N2O2S2. Calculated, %: С 68.62; H 5.12; N
5.93.
tert-Butyl
2,6-di(2-thienyl)-1-phenyl-4-phenyl-
amino-1,2,5,6-tetrahydropyridine-3-carboxylate (In).
Yield 4.01 g (78%), mp 180–181°C. IR spectrum, ν,
Ethyl
1-phenyl-4-phenylamino-2,6-di(4-ethyl-
1
cm–1: 3250 (NH), 1648 (C=O). Н NMR spectrum
phenyl)-1,2,5,6-tetrahydropyridine-3-carboxylate (Ik).
(400 MHz, CDCl3), δ, ppm (J, Hz): 1.58 s [9Н, OC
(СН3)3], 2.92 d.d (1H, C5HAHB, J 15.2, 12.0), 3.01 d.d
(1H, C5HAHB, J 15.2, 4.0), 4.93–4.97 m (1H, C6H),
6.19 s (1H, C2H), 6.81–7.41 m (16H, 2C6H5, thienyl),
10.60 s (1H, NH). 13С NMR spectrum (100 MHz,
CDCl3), δС, ppm: 27.73, 28.00, 36.48, 55.77, 59.31,
79.84, 100.15, 115.95, 123.31, 123.38, 123.43, 123.50,
124.05, 124.25, 125.94, 126.34, 128.16, 128.76,
138.22, 148.11, 149.69, 152.25, 155.53, 167.13.
Found, %: С 70.18; H 5.84; N 5.57. C30H30N2O2S2.
Calculated, %: С 70.01; H 5.87; N 5.44.
Yield 4.14 g (78%), mp 176–178°C. IR spectrum, ν,
1
cm–1: 3232 (NH), 1660 (C=O). Н NMR spectrum
(300 MHz, DMSO-d6), δ, ppm (J, Hz): 1.10 t (3H,
CH3CH2C6H4, J 7.5), 1.24 t (3H, CH3CH2C6H4, J 7.5),
1.41 t (3H, OCH2CH3, J 7.0), 2.46 d.d (1H, C5HAHB, J
15.6, 2.5), 2.53 q (2H, CH3CH2C6H4, J 7.5), 2.60 q
(2H, CH3CH2C6H4, J 7.5), 2.76 d.d (1H, C5HAHB, J
15.6, 5.8), 4.22 m (1H, OCHAHBCH3), 4.36 m (1H,
OCHAHBCH3), 5.19 m (1H, C6H), 6.21 s (1H, C2H),
6.29–7.41 m (18H, 2C6H5, 2C6H4), 10.11 s (1H, NH).
Found, %: С 81.56; H 7.25; N 5.39. C36H38N2O2.
Calculated, %: С 81.48; H 7.22; N 5.28.
Benzyl
1,2,6-triphenyl-4-phenylamino-1,2,5,6-
tetrahydropyridine-3-carboxylate (Io). Yield 3.86 g
Ethyl 2,6-di(2-thienyl)-1-phenyl-4-phenylamino-
1,2,5,6-tetrahydropyridine-3-carboxylate (Il). Yield
4.09 g (84%), mp 205–206°C. IR spectrum, ν, cm–1:
3240 (NH), 1656 (C=O). 1Н NMR spectrum
(400 MHz, CDCl3), δ, ppm (J, Hz): 1.37 t (3H,
OCH2CH3, J 7.0), 2.97 d.d (1H, C5HAHB, J 15.6, 12.2),
3.04 d.d (1H, C5HAHB, J 15.6, 4.2), 4.22 m (1H,
OCHAHBCH3), 4.39 m (1H, OCHAHBCH3), 4.93–5.01
m (1H, C6H), 6.26 s (1H, C2H), 6.81–7.41 m (16H,
2C6H5, 2-thienyl), 10.69 s (1H, NH). 13С NMR
spectrum (100 MHz, CDCl3), δС, ppm: 14.05, 36.52,
55.71, 59.11, 59.31, 98.50, 116.11, 118.87, 123.48,
123.52, 123.59, 124.10, 124.57, 125.99, 126.53,
128.53, 128.86, 138.00, 147.97, 149.64, 142.31,
156.55, 167.37. Found, %: С 69.22; H 5.35; N 5.78.
C28H26N2O2S2. Calculated, %: С 69.11; H 5.39; N
5.93.
(72%), mp 218–220°C. IR spectrum, ν, cm–1: 3240
1
(NH), 1648 (C=O). Н NMR spectrum (500 MHz,
DMSO-d6), δ, ppm (J, Hz): 2.70 d.d (1H, C5HAHB, J
15.6, 2.7), 2.82 d.d (1H, C5HAHB, J 15.6, 6.0), 4.01 d
(1H, OCHAHBC6H5, J 3.0), 4.08 d (1H, OCHAHBC6H5,
J 3.0), 5.40 m (1H, C6H), 6.34 s (1H, C2H), 6.37–7.61
m (25H, 5C6H5), 10.12 s (1H, NH). Found, %: С
82.69; H 6.04; N 5.35. C37H32N2O2. Calculated, %: С
82.81; H 6.01; N 5.22.
Methyl 1-(4-methylphenyl)-4-(4-methylphenyl-
amino)-2,6-diphenyl-1,2,5,6-tetrahydropyridine-3-
carboxylate (Ip). Yield 4.05 g (83%), mp 181–182°C.
1
IR spectrum, ν, cm–1: 3256 (NH), 1656 (C=O). Н
NMR spectrum (500 MHz, DMSO-d6), δ, ppm (J, Hz):
2.08 s (3H, 4-CH3C6H4), 2.22 s (3H, 4-CH3C6H4), 2.74
d.d (1H, C5HAHB, J 15.6, 2.3), 3.03 d.d (1H, C5HAHB,
J 15.6, 5.7), 3.84 s (3Н, OCH3), 5.14 m (1H, C6H),
6.07 s (1H, C2H), 6.15–7.14 m (18H, 2C6H4, 2C6H5),
10.01 s (1H, NH). Found, %: С 81.29; H 6.57; N 5.88.
C33H32N2O2. Calculated, %: С 81.12; H 6.60; N 5.73.
Isopropyl 2,6-di(2-thienyl)-1-phenyl-4-phenyl-
amino-1,2,5,6-tetrahydropyridine-3-carboxylate (Im).
Yield 3.95 g (79%), mp 209–210°C. IR spectrum, ν,
1
cm–1: 3240 (NH), 1648 (C=O). Н NMR spectrum
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 85 No. 4 2015