4-ALKYL-6-AMINO-4-N3,N5-DIARYL-2-THIOXO-1,2,3,4-…: I.
1399
ppm: 0.93 d (6Н, 2СН3, J 5.3 Hz), 1.06–1.20 m (1Н,
СН2), 1.28–1.40 m (1Н, СН2), 1.66–1.81 m (1Н,
СНМе2), 2.16 s (3H, СН3), 2.23 s (3Н, СН3), 3.39 br.s
Yield 0.19 g (79%) of yellow crystals, mp 158–160°C
(EtOH). IR spectrum, ν, cm–1: 3154, 3304, 3429 (NH,
NH2), 1675 (СОNH), 1627 [δ(NH2)]. 1Н NMR
spectrum, δ, ppm: 0.88 d (6Н, 2СН3, J 5.7 Hz), 1.03–
1.11 m (1Н, СН2), 1.26–1.36 m (1Н, СН2), 1.63–1.73
m (1Н, СНМе2), 2.27 s (3H, СН3), 2.28 s (3Н, СН3),
3.24 s (1Н, С3Н), 3.28–3.45 m (2Н, С4Н, SСН2), 3.73
d.d (1Н, SСН, J 13.5, J 6.3 Hz), 4.86 d (1Н, =СН2,
Jcis 9.8 Hz), 5.07 d (1Н, =СН2, Jtrans 16.7 Hz), 5.77–
5.87 m (1Н, СН=), 6.83 d (1Н, Нarom, J 7.1 Hz), 6.89 d
(1Н, Нarom, J 7.2 Hz), 7.15 t (1Н, Нarom, J 7.7 Hz), 7.20
t (1Н, Нarom, J 7.8 Hz), 7.29–7.51 m (6Н, 4Нarom, NH2),
9.21 br.s (1Н, NHСО), 9.60 br.s (1Н, NHСО). 13С
NMR spectrum, δС, ppm: 21.62, 21.67, 22.92, 23.94,
25.03, 33.17, 34.62, 42.91, 48.76, 111.45, 116.48,
117.10, 117.29, 120.39, 120.63, 123.91, 124.63, 128.81,
129.00, 136.47, 138.08, 138.30, 139.31, 139.90, 149.26,
159.04, 167.03, 167.08. Mass spectrum, m/z (Irel, %):
491.2 (100) [М + 1]+. Found, %: С 68.38; Н 6.87; N
11.30. C28H34N4O2S. Calculated, %: С 68.54; Н 6.99;
N 11.42. M 490.674.
2
3
(2Н, С3Н and С4Н), 3.47 d.d (1Н, SСН2, J 13.2, J
6.3 Hz), 3.74 d.d (1Н, SСН2, 2J 13.3, 3J 6.4 Hz), 4.87 d
(1Н, =СН2, Jcis 9.4 Hz), 5.11 d (1Н, =СН2, Jtrans 16.6 Hz),
5.76–5.90 m (1Н, СН=), 7.02 t (1Н, Нarom, J 8.0 Hz),
7.15–7.24 m (5Н, Нarom), 7.34 d (1Н, Нarom, J 7.6 Hz),
7.47 br.s (2Н, NH2), 7.65 d (1Н, Нarom, J 7.7 Hz), 8.74
br.s (1Н, NHСО), 8.88 br.s (1Н, NHСО). Mass
spectrum, m/z (Irel, %): 491.2 (100) [М + 1]+. Found,
%: С 68.37; Н 6.84; N 11.37. C28H34N4O2S.
Calculated, %: С 68.54; Н 6.98; N 11.42. M 490.674.
2
3
Ethyl-2-[6-amino-4-isobutyl-3,5-di(o-tolylcarba-
moyl)-4,5-dihydropyridine-2-ylsulfanyl]acetate (Vb).
Yield 0.086 g (32%), white powder, mp 161–163°C
(EtOH). IR spectrum, ν, cm–1: 3214–3433 (NH, NH2),
1
1712 (С=О), 1666 (СОNH), 1635 [δ(NH2)]. Н NMR
spectrum, δ, ppm: 0.80–1.05 m (6Н, 2СН3), 1.11 t (3Н,
СН3, J 7.0, Hz), 1.20–1.37 m (2Н, СН2), 1.66–1.77 m
(1Н, СНМе2), 2.15 s (3H, СН3), 2.22 s (3Н, СН3),
2
3.35 br.s (2Н, С3Н and С4Н), 3.68 d (1Н, SСН2, J
2-Amino-6-benzylsulfanyl-4-isobutyl-N3,N5-di-
m-tolyl-3,4-dihydropyridine-3,5-dicarboxamide (Ve).
Yield 0.16 g (58%), white powder, mp 192–194°C
(EtOH). IR spectrum, ν, cm–1: 3198–3413 (NH, NH2),
2
15.9 Hz), 3.85 d (1Н, SСН2, J 15.9 Hz), 3.97 m (2Н,
ОСН2), 7.00–7.35 m (7Н, Нarom), 7.51 d (1Н, Нarom, J
8.0 Hz), 7.54 br.s (1Н, NH2), 7.61 br.s (1Н, NH2), 8.64
br.s (1Н, NHСО), 8.72 br.s (1Н, NHСО). Mass
spectrum, m/z (Irel, %): 537.4 (100) [М + 1]+. Found,
%: С 64.73; Н 6.64; N 10.38. C29H36N4O4S. Cal-
culated, %: С 64.90; Н 6.76; N 10.44. M 536.70.
1
1677 (СОNH), 1640 [δ(NH2)]. Н NMR spectrum, δ,
ppm: 0.89 d (6Н, 2СН3, J 4.3 Hz), 1.05–1.19 m (1Н,
СН2), 1.23–1.37 m (1Н, СН2), 1.60–1.76 m (1Н,
СНМе2), 2.25 s (3H, СН3), 2.29 s (3Н, СН3), 3.36 t
(1Н, С4Н, J 6.4 Hz), 3.43 s (1Н, С3Н), 4.07 d (1Н,
SСН2, 2J 13.2 Hz), 4.33 d (1Н, SСН2, 2J 13.3 Hz), 6.80
d (1Н, Нarom, J 7.3 Hz), 6.89 d (1Н, Нarom, J 7.3 Hz),
7.01–7.65 m (13Н, 11Нarom, NH2), 8.96 br.s (1Н,
NHСО), 9.86 br.s (1Н, NHСО). Mass spectrum, m/z
(Irel, %): 541.2 (100) [М + 1]+. Found, %: С 71.12; Н
6.67; N 10.40. C32H36N4O2S. Calculated, %: С 71.08;
Н 6.71; N 10.36. М 540.73.
2-Amino-4-isobutyl-6-[2-(4-methoxyphenylamino)-
2-oxoethylsulfanyl]-N3,N5-di-o-tolyl-3,4-dihydro-
pyridine-3,5-dicarboxamide (Vc). Yield 0.163 g
(53%), yellowish green powder, mp 198–200°C
(EtOH). IR spectrum, ν, cm–1: 3212–3415 (NH, NH2),
1
1682 (СОNH), 1633 [δ(NH2)]. Н NMR spectrum, δ,
ppm: 0.93 d (6Н, 2СН3, J 5.8 Hz), 1.09–1.22 m (1Н,
СН2), 1.26–1.40 m (1Н, СН2), 1.68–1.82 m (1Н,
СНМе2), 2.14 s (3H, СН3), 2.20 s (3Н, СН3), 3.42 t
(1Н, С4Н, J 7.6 Hz), 3.48 s (1Н, С3Н), 3.64 d (1Н,
6-Allylsulfanyl-2-amino-4-isopropyl-N3,N5-di-o-
tolyl-3,4-dihydropyridine-3,5-dicarboxamide (Vf).
Yield 0.09 g (37%), yellowish green powder, mp 192–
194°C (EtOH). IR spectrum, ν, cm–1: 3208–3444 (NH,
NH2), 1666 (СОNH), 1634 [δ(NH2)]. 1Н NMR
spectrum, δ, ppm: 0.93 d (3Н, СН3, J 6.3 Hz), 0.97 d
(3Н, СН3, J 6.3 Hz), 1.56–1.74 m (1Н, СНМе2), 2.16 s
(3H, СН3), 2.22 s (3Н, СН3), 3.09 d (1Н, С4Н, J
7.2 Hz), 3.45 d.d (1Н, SСН2, 2J 13.4, 3J 6.6 Hz), 3.55 s
(1Н, С3Н), 3.73 d.d (1Н, СН2, 2J 13.4, 3J 6.6 Hz), 4.85
d (1Н, =СН2, Jcis 9.4 Hz), 5.10 d (1Н, =СН2, Jtrans 17.3
2
SСН2, J 14.2 Hz), 3.69 s (3Н, ОСН3), 3.89 d (1Н,
2
SСН2, J 14.2 Hz), 6.73 d (2Н, Нarom, J 8.5 Hz), 6.98–
7.27 m (7Н, Нarom), 7.32 d (2Н, Нarom, J 8.5 Hz), 7.46 d
(1Н, Нarom, J 7.6 Hz), 7.77 br.s (2Н, NH2), 8.86 br.s
(1Н, NHСО), 9.11 br.s (1Н, NHСО), 9.95 br.s (1Н,
NHСО). Mass spectrum, m/z (Irel, %): 614.4 (100)
[М + 1]+. Found, %: С 66.63; Н 6.32; N 11.47.
C34H39N5O4S. Calculated, %: С 66.53; Н 6.41; N
11.41. М 613.782.
6-Allylsulfanyl-2-amino-4-isobutyl-N3,N5-di-m-
tolyl-3,4-dihydropyridine-3,5-dicarboxamide (Vd).
Hz), 5.73–5.90 m (1Н, СН=), 7.02 t (1Н, Нarom
,
,
J 7.2 Hz), 7.05–7.27 m (5Н, Нarom), 7.34 d (1Н, Нarom
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 83 No. 7 2013