Arkivoc 2018, vii, 0-0
Sanad, S. M. H. et al.
Method B. To a mixture of bis(2-cyanoacetamides) 5a-d, aromatic aldehydes 13a-d (2.2 mmol) and
malononitrile 11 (2.2 mmol) in absolute ethanol (15 mL) piperidine (0.2 mL) was added. The mixture was
heated at reflux for 3 h. The crude solids were isolated and recrystallized from the proper solvent.
1
,1'-{[Propane-1,3-diylbis(sulfanediyl)]bis(2,1-phenylene)}bis(6-amino-2-oxo-4-phenyl-1,2-dihydropyridine-
o
3,5-dicarbonitrile) (7e). Brown crystals (Method A. 618 mg, 85%), mp208-210 C (Dioxane/EtOH, 25:75) IR (ῡ
-1
1
cm ): 3441, 3311 (NH
2
), 2214 (CN), 1679 (CO); H NMR (DMSO-d
S), 7.25-7.64 (m, 18H, ArH’s), 8.00 (s, br, 4H, 2 NH
15.4, 116.1, 127.4, 127.8, 128.6, 129.5, 130.3, 130.7, 132.0, 132.5, 134.4, 156.5, 158.7, 161.5; Anal. for
(728.85) Calcd: C, 67.57; H, 3.87; N, 15.37. Found: C, 67.88; H, 4.12; N, 15.02%.
,1'-{[Propane-1,3-diylbis(sulfanediyl)]bis(2,1-phenylene)}bis[6-amino-4-(4-chlorophenyl)-2-oxo-1,2-
dihydropyridine-3,5-dicarbonitrile] (7f). Brown crystals (Method A: 438 mg, 55%), mp200-202 oC
6
): δ
H
1.86-1.90 (m, 2H, SCH
2
CH
2
CH
2
S), 3.07 (t,
13
4H, SCH
2
CH
2
CH
2
2
); C NMR (DMSO-d
6
): δ
C
27.5, 29.7, 74.8,
1
C
1
41 28
H N
8
O
S
2 2
-1
1
(
(
C
1
Dioxane/EtOH, 25:75); IR (ῡ cm ): 3437, 3310 (NH
m, 2H, SCH CH CH S), 3.07 (t, 4H, SCH CH CH S), 7.40-7.68 (m, 16H, ArH’s), 8.04 (s, br, 4H, 2 NH
(797.73) Calcd: C, 61.73; H, 3.29; N, 14.05. Found: C, 61.99; H, 3.50; N, 14.20%.
,1'-{[Propane-1,3-diylbis(sulfanediyl)]bis(2,1-phenylene)}bis[6-amino-4-(4-methoxyphenyl)-2-oxo-1,2-
dihydropyridine-3,5-dicarbonitrile] (7g). Pale yellow crystals (Method A, 551 mg, 70%; Method B, 592 mg,
2
), 2216 (CN), 1678 (CO); H NMR (DMSO-d
): δ
6 H
1.85-1.92
2
2
2
2
2
2
2
); Anal. for
41
H26Cl
2
N
8
O
S
2 2
o
-1
1
7
1
5%), mp164-166 C (EtOH); IR (ῡ cm ): 3448, 3304 (NH
.88 (m, 2H, SCH CH CH S), 3.07 (t, 4H, SCH CH CH S), 3.86 (s, 6H, 2 OCH
); C NMR (DMSO-d ): δ 27.8, 31.7, 55.2, 74.9, 113.9, 115.8, 116.4, 120.7, 126.4, 127.4, 129.5,
(788.90) Calcd: C, 65.47; H, 4.09;
2
), 2215 (CN), 1669 (CO); H NMR (DMSO-d
), 6.92-7.60 (m, 16H, ArH’s), 8.03 (s,
6
): δ 1.84-
H
2
2
2
2
2
2
3
13
br, 4H, 2 NH
2
6
C
129.7, 130.5, 132.5, 135.7, 156.6, 158.9, 160.7, 161.0; Anal. for C43
32
H N
8
O
S
4 2
N, 14.20. Found: C, 65.19; H, 4.31; N, 14.32%.
1
,1'-{[Propane-1,3-diylbis(sulfanediyl)]bis(2,1-phenylene)}bis[6-amino-4-(benzo[d][1,3]dioxol-5-yl)-2-oxo-
o
1,2-dihydropyridine-3,5-dicarbonitrile] (7h). Pale yellow crystals (Method A, 587 mg, 72%), mp208-210 C
-1
1
(
(
4
1
1
3
Dioxane/EtOH, 25:75); IR (ῡ cm ): 3442, 3326 (NH
m, 2H, SCH CH CH S), 3.09 (t, 4H, SCH CH CH S), 6.16 (s, 4H, 2 OCH
); Anal. for C43 (816.87) Calcd: C, 63.23; H, 3.46; N, 13.72. Found: C, 63.00; H, 3.70; N,
2
), 2216 (CN), 1675 (CO); H NMR (DMSO-d
O), 6.86-7.62 (m, 14H, ArH’s), 7.95 (s, br,
6
): δ 1.84.1.88
H
2
2
2
2
2
2
2
H, 2 NH
2
28
H N
8
O
S
6 2
3.99%.
,1'-{[Butane-1,4-diylbis(sulfanediyl)]bis(2,1-phenylene)}bis(6-amino-2-oxo-4-phenyl-1,2-dihydropyridine-
,5-dicarbonitrile) (7i). Pale yellow crystals (Method A 504 mg, 68%), mp> 300 C (Dioxane/EtOH, 25:75); IR (ῡ
o
-1
1
cm ): 3443, 3315 (NH
2
), 2214 (CN), 1677 (CO); H NMR (DMSO-d
S), 7.40-7.57 (m, 18H, ArH’s), 7.96 (s, br, 4H, 2 NH
4.9, 115.5, 116.2, 120.7, 124.9, 127.5, 127.9, 128.6, 129.7, 130.3, 130.7, 132.3, 134.5, 135.6, 156.6, 158.8,
61.6; Anal. for C42 (742.88) Calcd: C, 67.91; H, 4.07; N, 15.08. Found: C, 67.78; H, 4.24; N, 15.33%.
,1'-{[Butane-1,4-diylbis(sulfanediyl)]bis(2,1-phenylene)}bis[6-amino-4-(4-chlorophenyl)-2-oxo-1,2-
): δ
6 H
1.69 (t, 4H, SCH
2
CH
2
CH
2
CH
C
2
S), 2.98 (t,
27.5, 31.2,
1
3
4
7
1
1
H, SCH
2
CH
CH CH
2 2 2
2
); C NMR (DMSO-d
6
): δ
30
H N
8
O
S
2 2
dihydropyridine-3,5-dicarbonitrile] (7j). Brown crystals (Method A: 405 mg, 50%), mp180-182 oC
-1
1
(
Dioxane/EtOH, 25:75); IR (ῡ cm ): 3439, 3308 (NH
SCH CH CH CH S), 2.97 (t, 4H, SCH CH CH CH S), 7.22-7.67 (m, 16H, ArH’s), 8.03 (s, br, 4H, 2 NH
(811.76) Calcd: C, 62.14; H, 3.48; N, 13.80. Found: C, 62.48; H, 3.66; N, 13.58%.
2
), 2213 (CN), 1676 (CO); H NMR (DMSO-d
6
): δ
H
1.68 (t, 4H,
); Anal. for
2
2
2
2
2
2
2
2
2
C
42
H28Cl
2
N
8
O
S
2 2
1
,1'-{[Pentane-1,5-diylbis(sulfanediyl)]bis(2,1-phenylene)}bis(6-amino-2-oxo-4-phenyl-1,2-dihydropyridine-
o
3,5-dicarbonitrile) (7k). Pale orange crystals (Method A: 522 mg, 69%), mp192-194 C (Dioxane/EtOH, 25:75);
-
1
1
IR (ῡ cm ): 3440, 3314 (NH
SCH CH CH CH CH S), 2.95 (t, 4H, SCH
NMR (DMSO-d ): δ 27.2, 27.9, 31.7, 74.8, 115.4, 115.9, 120.2, 126.3, 127.4, 127.8, 129.8, 130.2, 130.6, 132.3,
2
), 2216 (CN), 1680 (CO); H NMR (DMSO-d
6
): δ
H
1.55.1.58 (m, 6H,
13
2
2
2
2
2
2
CH CH CH CH S), 7.23-7.57 (m, 18H, ArH’s), 7.96 (s, br, 4H, 2 NH ); C
2
2
2
2
2
6
C
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