1
070
Can. J. Chem. Vol. 84, 2006
1
1
434, 1399, 1371, 1294, 1253, 1178, 1033, 965, 744. H
(ddd, J = 8.3, 7.9, 2.9 Hz, 2H), 7.55 (s br, 2H), 7.57 (ddd,
J = 8.3, 7.9, 2.9 Hz, 3H), 7.64 (ddd, J = 8.3, 7.9, 2.2 Hz,
2H), 7.89 (d, J = 8.3Hz, 1H), 8.02 (dd, J = 8.2, 2.2 Hz, 2H).
NMR (200 MHz, CDCl ) δ: 5.32 (t, J = 3.9 Hz, 1H), 7.02 (d,
J = 3.9 Hz, 2H), 7.17 (d, J = 8.4 Hz, 4H), 7.25 (s br, 2H,
NH ), 7.49 (dd, J = 8.4, 3.2 Hz, 6H), 7.70 (m, 7H), 8.10 (d,
J = 8.5 Hz, 2H). C NMR (CDCl ) δ: 54.8, 114.5, 121.6,
22.3, 127.9, 128.4, 129.7, 131.5, 139.4, 151.1. HR EI-MS
m/z: 400.1979 (M , 5) (calcd. for C H N : 400.1939), 323
[M – C H ], 36), 246 (100), 154 (33), 101 (47), 88 (65).
3
1
3
C NMR(DMSO-d ) δ : 54.3, 108.9, 111.7, 121.9, 123.0,
2
6
C
1
3
123.8, 126.4, 125.3, 128.0, 128.9, 129.8, 130.7, 133.5,
3
+
1
135.6, 143.9,151.1. HR EI-MS m/z: 470, 468.1109 (M , 13)
+
+
(calc. for C H Cl N , 468.1120), 323 ([M – C H Cl ],
2
9
24
2
29 22
2
2
6
3
2
+
+
(
30), 246 ([M – C H Cl – C H ], 100), 169 (56), 155 (41),
6
5
6 3 2 6 5
Anal. calcd. for C H N : C 86.95, H 6.05, N 6.99; found:
C 87.38, H 5.98, N 6.72.
77 (70). Anal. calcd. for C H Cl N : C 74.34, H 4.74, N
29 22 2 2
5.98; found: C 75.01, H 4.68, N 6.30.
2
9
24
2
1
-(2-Aminophenyl)-4(4-methoxyphenyl)-2,6-diphenyl-1,4-
1-(2-Aminophenyl)-2,6-di(4-chloro)phenyl-4-phenyl-1,4-
dihydropyridine (3f)
dihydropyridine (3b)
–
1
–1
Colourless crystals, mp 183 °C. IR (cm ) υmax: 3435,
Colourless crystals, mp 202 °C. IR (cm ) υmax: 3456,
3
1
3
2
3
(
1
1
036, 3004, 2940–2673 (m), 1610, 1500, 1470, 1455, 1435,
3030, 2669–2945 (m), 1610, 1475, 1496, 1387, 1350, 1140,
1
1
399, 1371, 1294, 1253, 1030, 967. H NMR (DMSO-d ) δ:
1090, 1072, 926. H NMR (DMSO-d ) δ: 5.35 (t, J = 3.9 Hz,
6
6
.84 (s, 3H), 5.35 (t, J = 3.8 Hz, 1H), 7.15 (d, J = 3.8 Hz,
H), 7.17 (d, J = 8.4 Hz, 2H), 7.33 (ddd, J = 6.9, 8.4,
.9 Hz, 6H), 7.35 (s, br, 2H), 7.69 (d, J = 8.4 Hz, 6H), 7.80
1H), 7.06 (d, J = 3.9 Hz, 2H), 7.26 (d, J = 8.2 Hz, 4H), 7.45
(m, 5H), 7.55 (s br, 2H), 7.63 (dd, J = 8.2, 2.2 Hz, 2H), 7.64
(dd, J = 8.2, 2.2 Hz, 4H), 8.02 (dd, J = 8.2, 1.6 Hz, 2H).
d, J = 6.9 Hz, 4H). 13C NMR (DMSO-d ) δ : 54.8, 55.3,
13
C NMR (DMSO-d ) δ: 54.1, 111.3, 118.7, 121.6, 122.5,
6
C
6
14.6, 116.5, 127.6, 127.7, 128.4, 128.6, 131.2, 143.0,
49.1, 158.6. HR EI-MS m/z: 430.2015 (20) (calcd. for
126.4, 128.9, 129.8, 130.1, 135.0, 143.7, 151.2. HR EI-MS
m/z (rel. int): 468.1110 (10) (calcd. for C H Cl N :
2
9
22
2
2
+
C H N O: 430.2045), 416 (35), 353 (40), 246 (100), 154
468.1101), 391 [M - Ph], 280 (100), 188 (57), 169 (46), 77
(62). Anal. calcd. for CHN: not found.
3
0
26
2
(
45), 101 (53), 88 (71). Anal. calcd. for C H N O: C
30 26 2
8
3.68, H 6.09, N 6.50; found: C 83.72, H 6.12, N 6.20.
1
-(2-Aminophenyl)-4-(4-bromo)phenyl-2,6-diphenyl-1,4-
1
-(2-Aminophenyl)-4(4-fluoro)phenyl-2,6-diphenyl-1, 4-
dihydropyridine (3g)
–
1
dihydropyridine (3c)
Colourless crystals, mp 178 °C. IR (cm ) υmax: 3435,
–
1
Colourless crystals, mp 102 °C. IR (cm ) υmax: 3436,
3050, 1605, 1545, 1490, 1387, 1350, 1150, 1095, 920, 760.
1
3
1
5
035, 3004, 2943–2675 (m), 1618, 1500, 1470, 1455, 1430,
H NMR (CDCl ) δ: 5.37 (t, J = 3.9 Hz, 6H), 7.16 (d, J =
3
1
398, 1371, 1294, 1253, 1030, 967. H NMR (DMSO-d ) δ:
3.9 Hz, 2H), 7.26 (m, 4H), 7.36 (s br, 2H), 7.39 (dd, J = 8.7,
3.9 Hz, 2H), 7.51 (s, br, 2H), 7.58 (ddd, J = 8.3, 2.4, 8.3 Hz,
4H), 7.72 (d, J = 8.7 Hz, 2H), 8.28 (ddd, J = 8.3, 2.4,
8.3 Hz, 2H). C NMR (DMSO-d ) δ : 55.9, 111.6, 118.9,
122.3, 125.6, 128.3, 129.7, 130.1, 131.9, 143.9, 151.1,
6
.75 (d, J = 3.9 Hz, 1H), 7.09 (t, J = 3.9 Hz, 1H), 7.16 (d,
J = 8.7 Hz, 3H), 7.18 (m, 10H), 7.35 (sbr, 2H), 7.49 (dd, J =
1
3
13
8
.7, 3.9 Hz, 4H), 8.10 (d, J = 3.9 Hz, 2H). C NMR
6
C
(
DMSO-d ) δ : 57.2, 114.3, 115.8, 121.7, 122.6, 124.6,
6
C
+
1
28.9, 129.8, 130.1, 134.9, 143.7, 151.2, 160.5. HR EI-MS
160.3. HR EI-MS m/z: 480.1018(13), 478.1030 (M , 10)
+
m/z: 418.1846 (18) (calcd. for C H FN : 418.1851), 323
(calcd. for C H BrN : 478.1025), 323 ([M – C H Br],
2
9
23
2
29 23
2
6
5
+
+
(
(
[M – C H F], 46), 246 ([M – C H F – C H ], 100), 92
70), 77 (76). Anal. calcd for C H FN : C 83.22, H 5.55, N
40), 246 (100), 169 (58), 144 (67), 77 (70). Anal. calcd. for
C H BrN : C 72.79, H 4.8, N 5.8; found: C 73.01, H 5.23,
6
4
6
4
6
5
29 23 2
29 23
2
6
.69; found: C 83.35, H 5.42, N 6.20.
-(2-Aminophenyl)-4(4-chloro)phenyl-2,6-diphenyl-1,4-
N 4.26.
1
1-(2-Aminophenyl)-4(3,4-dioxymethylene)phenyl-2,6-
diphenyl-1,4-dihydropyridine (3h)
Colourless crystals, mp 173 °C. IR (cm ) υmax: 3439,
3165, 3047, 2964–2531 (m), 1590, 1494, 1385, 1350, 1260,
1140, 1096, 920 760. H NMR (CDCl ) δ: 5.45 (t, J = 3.9 Hz,
1H), 6.02 (s, 2H), 7.10 (d, J = 3.9 Hz, 1H), 7.23 (s br, 2H,
dihydropyridine (3d)
–
1
–1
Colourless crystals, mp 189 °C. IR (cm ) υmax: 3437,
3
1
5
010, 2945–2669 (m), 1620, 1480, 1456, 1434, 1399, 1370,
1
1
295, 1253, 1178, 1033, 965, 745. H NMR (DMSO-d ) δ:
6
3
.37 (d, J = 3.9 Hz, 1H), 7.09 (t, J = 3.9 Hz, 1H), 7.26 (d,
J = 8.2 Hz, 4H), 7.46 (m, 13H), 7.37 (s br, 2H), 8.0 (d, J =
NH ), 7.26 (dd, J = 8.5, 3.9 Hz, 4H), 7.35 (ddd, J = 8.1, 2.2,
2
1
3
3
1
1
.9 Hz, 2H). C NMR (DMSO-d ) δ : 55.8, 111.2, 118.7,
8.3 Hz, 6H), 7.50 (ddd, J = 8.3, 2.4, 8.3 Hz, 5H), 7.53 (d,
6
C
13
21.5, 122.4, 126.3, 128.8, 129.7, 130.0, 134.9, 143.7,
J = 8.3 Hz, 2H), 8.25 (d, J = 8.3 Hz, 1H). C NMR (DMSO-
d ) δ : 55.3, 101.2, 114.5, 118.6, 122.8, 126.7, 128.3, 129.5,
+
51.1. HR EI-MS m/z: 436.1535, 434.1540 (M , 6) (calcd.
6
C
+
for C H ClN : 436.1520, 334.1520), 222 ([M – C H Cl],
3
135.5, 135.8, 147.3, 147.9, 149.3, 153.3. HR EI-MS m/z
2
9
23
2
6
5
+
+
0), 246 ([M – C H Cl – C H ], 100), 92 (73), 77 (67).
(rel.int): 444.1830+ (M , 7) (calcd. for C H N O :
6
5
6
5
30 24
2
2
Anal. calcd. for C H ClN : C 79.79, H 5.34, N 6.45;
444.1839), 414 ([M – HCHO], 20), 323 (15), 293 (21), 246
(100), 169 (52), 144 (56), 77 (70). Anal. calcd. C 81.04, H
2
9
23
2
found: C 80.20, H 4.95, N 5.98.
5
.44, N 6.30; found: C 82.10, H 5.70, N 5.85.
1
1
-(2-Aminophenyl)-4-(3,4-dichlorophenyl)-2,6-diphenyl-
,4-dihydropyridine (3e)
1-(2-Aminophenyl)-4(4-hydroxy)phenyl-2,6-diphenyl-1,4-
dihydropyridine (3i)
–
1
Colourless crystals, mp 235 °C. IR (cm ) υmax: 3435,
–
1
3
1
3
050, 2945–2669 (m), 1605, 1550, 1497, 1387, 1350, 1148,
Colourless crystals, mp 235 °C. IR (cm ) υmax: 3560,
1
090, 1018, 970, 730. H NMR (DMSO-d ) δ: 5.38 (t, J =
3430, 3265, 3050, 2964–2531 (m), 1605, 1550, 1485, 1380,
1345, 1280, 1140, 1096, 920, 750. H NMR (DMSO-d ) δ:
6
1
.9 Hz, 1H), 7.17 (d, J = 3.9 Hz, 1H), 7.38 (m, 8H), 7.50
6
©
2006 NRC Canada