O. Firuzi et al.
3-Isopropyl-5-(3-(pyridine-4-yl)propyl)-2,6-dimethyl-4-(4-
nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate (7h)
j = 5.9 Hz), 7.37 (t, 1H, C5H-phenyl, j = 7.9 Hz), 7.64 (d,
1H, C6H-phenyl, j = 7.7 Hz), 7.99 (d, 1H, C4H-phenyl,
j = 7.8 Hz), 8.14 (s, 1H, C2H-phenyl), 8.47 (d, 2H, C3,5H-
pyridyl, j = 5.9 Hz).
1H-NMR (CDCl3, 500 Hz): d 1.12–1.24 (2d, 6H, CO-
OCH(CH3)2, j = 6.2, 6.2 Hz), 1.88–1.94 (m, 2H, CO-
OCH2CH2CH2), 2.34–2.36 (2s, 6H, C2–CH3 and C6–CH3),
2.56 (t, 2H, COOCH2CH2CH2, j = 7.7 Hz), 4.03–4.09 (m,
2H, COOCH2CH2CH2), 4.95–4.98 (m, 1H, COOCH(CH3)2),
5.10 (s, 1H, C4–H), 5.86 (brs, 1H, NH–DHP), 7.02 (d, 2H,
Found C, 64.41; H, 5.83; N, 9.01 %. Anal.
(C25H27N3O6) requires C, 64.50; H, 5.85; N, 9.03 %.
MS: (m/z) 448 (35), 343 (100), 329 (4), 297 (50), 196
(16), 136 (9), 120 (18), 106 (13), 92 (12), 77 (2), 51 (1).
IR (KBr): t 3272 (NH), 3068 (CH-aromatic), 2957 (CH-
aliphatic), 1697 (CO), 1348, 1524 cm-1 (NO2).
C2,6H-pyridyl, j = 5.8 Hz), 7.45 (d, 2H, C2,6H-phenyl,
j = 8.7 Hz), 8.07 (d, 2H, C3,5H-phenyl, j = 8.7 Hz), 8.47 (d,
2H, C3,5H-pyridyl, j = 5.9 Hz).
3-Isopropyl-5-(3-(pyridine-2-yl)propyl)-2,6-dimethyl-4-(3-
nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate (7f)
Found C, 64.98; H, 6.11; N, 8.79 %. Anal.
(C26H29N3O6) requires C, 65.12; H, 6.10; N, 8.76 %.
MS: (m/z) 480 (2), 462 (39), 448 (2), 420 (10), 434 (4),
392 (8), 375 (2), 297 (46), 271 (18), 196 (19), 136 (8), 120
(30), 106 (8), 92 (24), 77 (8), 51 (5).
1H-NMR (CDCl3, 500 Hz): d 1.10–1.26 (2d, 6H, CO-
OCH(CH3)2, j = 6.2, 6.2), 2.02–2.07 (m, 2H, CO-
OCH2CH2CH2), 2.34–2.37 (2s, 6H, C2–CH3 and C6–CH3),
2.75 (t, 2H, COOCH2CH2CH2, j = 7.6 Hz), 4.04–4.12 (m,
2H, COOCH2CH2CH2), 4.93–4.98 (m, 1H, COOCH(CH3)2),
5.09 (s, 1H, C4–H), 5.72 (brs, 1H, NH–DHP), 7.04 (d, 1H,
C6H-pyridyl, j = 7.7 Hz), 7.09 (t, 1H, C4H-pyridyl,
j = 8.4 Hz), 7.35 (t, 1H, C5H-phenyl, j = 8.8 Hz), 7.56 (t,
1H, C5H-pyridyl, j = 7.0 Hz), 7.65 (d, 1H, C6H-phenyl,
j = 7.7 Hz), 7.98 (d, 1H, C4H-phenyl, j = 8.2 Hz), 8.14 (s,
1H, C2H-phenyl), 8.50 (d, 1H, C3H-pyridyl, j = 4.8 Hz).
Found C, 64.99; H, 6.13; N, 8.73 %. Anal.
(C26H29N3O6) requires C, 65.12; H, 6.10; N, 8.76 %.
MS: (m/z) 462 (3), 420 (3), 343 (3), 196 (5), 136 (5), 120
(100), 106 (13), 93 (10), 78 (2).
IR (KBr): t 3196 (NH), 3076 (CH-aromatic), 2971 (CH-
aliphatic), 1701, 1674 (CO), 1346, 1511 cm-1 (NO2).
3-Ethyl-5-(3-(pyridine-3-yl)propyl)-2,6-dimethyl-4-(3-
nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate (7i)
1H-NMR (CDCl3, 500 Hz): d 1.23 (t, 3H, COOCH2CH3,
j = 7.5 Hz), 1.90–1.93 (m, 2H, COOCH2CH2CH2), 2.34–2.38
(2s, 6H, C2–CH3 and C6–CH3), 2.57(t, 2H, COOCH2CH2CH2,
j = 7.7 Hz), 4.04–4.11 (m, 4H, COOCH2CH2CH2 and
COOCH2CH3), 5.11 (s, 1H, C4–H), 5.91 (brs, 1H, NH–DHP),
7.20 (t, 1H, C5H-pyridyl), 7.37 (t, 1H, C5H-phenyl,
j = 7.9 Hz), 7.41 (d, 1H, C6H-phenyl, j = 7.7 Hz), 7.64 (d,
1H, C6H-pyridyl, j = 7.5 Hz), 7.99 (d, 1H, C4H-phenyl,
j = 7.8 Hz), 8.13 (s, 1H, C2H-phenyl), 8.37 (s, 1H, C2H-pyr-
idyl), 8.44 (d, 1H, C4H-pyridyl).
IR (KBr): t 3207 (NH), 3089 (CH-aromatic), 2976 (CH-
aliphatic), 1695, 1670(CO), 1346, 1525 cm-1 (NO2).
3-Isopropyl-5-(3-(pyridine-3-yl)propyl)-2,6-dimethyl-4-(3-
nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate (7g)
Found C, 64.71; H, 5.90; N, 9.09 %. Anal.
(C25H27N3O6) requires C, 64.50; H, 5.85; N, 9.03 %.
MS: (m/z) 466 (2), 447 (45), 420 (3), 343 (44), 329 (6),
297 (91), 196 (29), 136 (13), 120 (25), 106 (21), 92 (56), 78
(8), 51 (5).
1H-NMR (CDCl3, 500 Hz): d 1.11–1.26 (2d, 6H, CO-
OCH(CH3)2, j = 6.2, 6.2 Hz), 1.88–1.94 (m, 2H, CO-
OCH2CH2CH2), 2.35–2.38 (2s, 6H, C2–CH3 and C6–CH3),
2.58 (t, 2H, COOCH2CH2CH2, j = 7.7 Hz), 4.01–4.11 (m,
2H, COOCH2CH2CH2), 4.94–4.99 (m, 1H, COOCH(CH3)2),
5.10 (s, 1H, C4–H), 5.80 (brs, 1H, NH–DHP), 7.18–7.21 (dd,
1H, C5H-pyridyl), 7.37 (t, 1H, C5H-phenyl, j = 8.8 Hz), 7.41
(d, 1H, C6H-phenyl, j = 7.7 Hz), 7.64 (d, 1H, C6H-pyridyl,
j = 7.7 Hz), 7.99 (d, 1H, C4H-phenyl, j = 8.3 Hz), 8.14 (s,
1H, C2H-phenyl), 8.37 (s, 1H, C2H-pyridyl), 8.43 (d, 1H, C4H-
pyridyl, j = 4.7 Hz).
IR (KBr): t 3206 (NH), 3081 (CH-aromatic), 2979 (CH-
aliphatic), 1692 (CO), 1342, 1522 cm-1 (NO2).
3-Methyl-5-(3-(pyridine-3-yl)propyl)-2,6-dimethyl-4-(1-
methyl-5-nitro-1-imidazole-2-yl)-1,4-dihydropyridine-3,5-
dicarboxylate (7j)
1H-NMR (CDCl3, 500 Hz): d 1.92–1.98 (m, 2H, CO-
OCH2CH2CH2), 2.25–2.26 (2s, 6H, C2–CH3 and C6–CH3),
2.63 (t, 2H, COOCH2CH2CH2, j = 7.7 Hz), 3.68 (s, 3H, N–
CH3), 4.08–4.16 (m, 2H, COOCH2CH2CH2), 4.21 (s, 3H,
COOCH3), 5.14 (s, 1H, C4–H), 7.19–7.21 (dd, 1H, C5H-
pyridyl), 7.45 (d, 1H, C6H-pyridyl, j = 7.7 Hz), 7.95 (s, 1H,
H–Imidazole), 8.41 (s, 1H, C2H-pyridyl), 8.45 (d, 1H, C4H-
pyridyl, j = 3.3 Hz), 8.45 (brs, 1H, NH–DHP).
Found C, 65.07; H, 6.12; N, 8.77 %. Anal.
(C26H29N3O6) requires C, 65.12; H, 6.10; N, 8.76 %.
MS: (m/z) 480 (2), 461 (46), 447 (3), 343 (10), 329 (1), 297
(100), 196 (25), 136 (15), 120 (40), 106 (26), 92 (77), 77 (10),
51 (6).
IR (KBr): t 3208 (NH), 3087 (CH-aromatic), 2979 (CH-
aliphatic), 1695 (CO), 1347, 1522 cm-1 (NO2).
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