Vol. 64, No. 9 (2016)
Chem. Pharm. Bull.
1285
target compounds 1a–3c. Compounds 1b and 2b were synthe-
4-[2-(1-(4-Chlorophenyl)ethylidene)hydrazinyl]-1-(3-
2
3)
sized in our previous study.
-Phenethyl-4-[2-(1-phenylethylidene)hydrazinyl]pyridinium
Bromide (1a)
phenylpropyl)pyridinium Bromide (2b)
Yield 63%; mp 115°C; IR (KBr) cm : 3425, 3020, 2951,
2832, 1643, 1583, 1538, 1513, 1482, 823, 763, 680. H-NMR
−1
1
1
−1
Yield 65%; mp 152°C; IR (KBr) cm : 3435, 3033, 2960, (400MHz, DMSO-d ) δ ppm: 2.15 (2H, quin, J=8.0Hz,
6
1
+
2
860, 1645, 1578, 1555, 1539, 1184, 835, 760, 746. H-NMR N –CH –CH –CH –Ph), 2.44 (3H, s, CH ), 2.61 (2H, t,
2
2
2
3
+
(
400MHz, DMSO-d ) δ ppm: 2.44 (3H, s, CH ), 3.16 (2H, t, J=8.0Hz, N –CH –CH –CH –Ph), 4.32 (2H, t, J=8.0Hz,
6
3
2
2
2
+
+
+
J=7.0Hz, N –CH –CH –Ph), 4.54 (2H, t, J=7.0Hz, N –CH – N –CH –CH –CH –Ph), 7.18–7.31 (5H, m, Ar-H), 7.45 (1H,
2
2
2
2
2
2
CH –Ph), 7.20–7.32 (5H, m, Ar-H), 7.37 (1H, d, J=7.6Hz, pyr- d, J=8.0Hz, pyridinium-H), 7.52 (2H, d, J=8.0Hz, Ar-H),
2
idinium-H), 7.44–7.47 (3H, m, Ar-H), 7.61 (1H, d, J=7.6Hz, 7.68 (1H, d, J=8.0Hz, pyridinium-H), 7.94 (2H, d, J=8.0Hz,
pyridinium-H), 7.89–7.93 (2H, m, Ar-H), 8.34 (2H, brs, pyri- Ar-H), 8.48 (2H, dd, J=4.0/8.0Hz, pyridinium-H), 11.31 (1H,
13
13
dinium-H), 11.24 (1H, brs, NH). C-NMR (100MHz, DMSO- brs, NH). C-NMR (100MHz, DMSO-d ) δ ppm: 15.22,
6
d6) δ ppm: 15.30, 36.67, 58.83, 107.81, 109.76, 126.94, 127.32, 32.02, 32.36, 57.82, 108.19, 110.11, 126.49, 128.65, 128.70,
1
28.94, 129.00, 129.36, 130.20, 137.07, 137.75, 143.21, 144.49, 128.85, 128.93, 134.86, 136.60, 140.93, 143.31, 144.55, 151.94,
+
+
+
+
153.30, 154.91. HR-MS (ESI ) Calcd for C H N 316.1814. 154.96. HR-MS (ESI ) Calcd for C H ClN 364.1581. Found
2
1
22
3
22 23
3
Found 316.1818.
364.1585.
4
-[2-(1-Phenylethylidene)hydrazinyl]-1-(3-phenylpropyl)-
pyridinium Bromide (1b)
Yield 60%; mp 106°C; IR (KBr) cm : 3480, 3010, 2990,
4-[2-(1-(4-Chlorophenyl)ethylidene)hydrazinyl]-1-(2-
phenoxyethyl)pyridinium Bromide (2c)
Yield 82%; mp 235°C; IR (KBr) cm : 3375, 3060, 2904,
−
1
−1
1
1
2
860, 1644, 1538, 1445, 840, 754, 692. H-NMR (400MHz, 1643, 1541, 1488, 1242, 1189, 1089, 832, 789, 760. H-NMR
DMSO-d ) δ ppm: 2.17 (2H, quin, J=7.4Hz, N –CH –CH – (400MHz, DMSO-d ) δ ppm: 2.43 (3H, s, CH ), 4.39 (2H,
+
6
2
+
2
6
3
+
CH –Ph), 2.47 (3H, s, CH ), 2.64 (2H, t, J=7.4Hz, N –CH – t, J=7.0Hz, N –CH –CH –O–Ph), 4.68 (2H, t, J=7.0Hz,
2
3
2
2
2
+
+
CH –CH –Ph), 4.33 (2H, t, J=7.4Hz, N –CH –CH –CH – N –CH –CH –O–Ph), 6.91–6.96 (3H, m, Ar-H), 7.27 (2H, t,
2
2
2
2
2
2
2
Ph), 7.20–7.33 (5H, m, Ar-H), 7.45–7.49 (4H, m, pyridinium- J=8.0Hz, Ar-H), 7.48 (2H, d, J=8.0Hz, Ar-H), 7.67 (1H, d,
H, Ar-3H), 7.69 (1H, d, J=7.6Hz, pyridinium-H), 7.93–7.95 J=8.0Hz, pyridinium-H), 7.79 (1H, d, J=8.0Hz, pyridinium-
2H, m, Ar-H), 8.48 (2H, dd, J=3.7/7.7Hz, pyridinium-H), H), 7.92 (2H, d, J=8.0Hz, Ar-H), 8.50 (1H, d, J=8.0Hz,
1
(
1
1
1
3
1.30 (1H, brs, NH). C-NMR (100MHz, DMSO-d ) δ ppm: pyridinium-H), 8.53 (1H, d, J=8.0Hz, pyridinium-H), 12.09
6
13
5.24, 32.02, 32.33, 57.79, 108.09, 110.02, 126.50, 126.92, (1H, brs, NH). C-NMR (100MHz, DMSO-d ) δ ppm: 15.52,
6
1
28.66, 128.86, 128.96, 130.20, 137.80, 140.94, 143.26, 144.53, 57.21, 66.81, 107.87, 109.97, 115.05, 121.73, 128.72, 128.90,
+
+
153.22, 154.98. HR-MS (ESI ) Calcd for C H N 330.1970. 130.01, 134.87, 136.73, 143.61, 144.99, 152.39, 155.41, 158.10.
2
2
24
3
+
+
Found 330.1983.
HR-MS (ESI ) Calcd for C H ClN O 366.1373. Found
21 21 3
1-(2-Phenoxyethyl)-4-[2-(1-phenylethylidene)hydrazinyl]- 366.1382.
pyridinium Bromide (1c)
Yield 77%; mp 203°C; IR (KBr) cm : 3470, 3070, 2917, phenethylpyridinium Bromide (3a)
4-[2-(1-(Benzofuran-2-yl)ethylidene)hydrazinyl]-1-
−1
1
−1
1644, 1539, 1490, 1443, 1189, 1050, 842, 764. H-NMR
Yield 64%; mp 130°C; IR (KBr) cm : 3408, 3028, 2904,
1
(
400MHz, DMSO-d ) δ ppm: 2.50 (3H, s, CH ), 4.36 (2H, 1639, 1579, 1532, 1448, 1181, 836, 742. H-NMR (400MHz,
6
3
+
t, J=7.0Hz, N –CH –CH –O–Ph), 4.65 (2H, t, J=7.0Hz, DMSO-d ) δ ppm: 2.50 (3H, s, CH ), 3.20 (2H, t, J=7.0Hz,
N –CH –CH –O–Ph), 6.88–6.92 (3H, m, Ar-H), 7.23 (2H, N –CH –CH –Ph), 4.59 (2H, t, J=7.0Hz, N –CH –CH –
2
2
6
3
+
+
+
2
2
2
2
2
2
t, J=8.0Hz, Ar-H), 7.39–7.41 (3H, m, Ar-H), 7.61 (1H, d, Ph), 7.23–7.34 (6H, m, pyridinium-1H, Ar-5H), 7.42 (1H, td,
J=8.0Hz, pyridinium-H), 7.85–7.87 (3H, m, pyridinium-1H, J=1.2/8.0Hz, benzofuran-H), 7.55–7.58 (3H, m, pyridinium-
Ar-2H), 8.49 (2H, dd, J=3.7/8.0Hz, pyridinium-H), 12.19 (1H, 1H, benzofuran-2H), 7.66 (1H, d, J=8.0Hz, benzofuran-H),
1
3
brs, NH). C-NMR (100MHz, DMSO-d ) δ ppm: 15.79, 57.13, 7.72 (1H, d, J=8.0Hz, benzofuran-H), 8.47 (2H, brs, pyridi-
6
13
6
6.84, 107.72, 109.87, 115.05, 121.71, 126.93, 128.89, 130.00, nium-H), 11.49 (1H, brs, NH). C-NMR (100MHz, DMSO-
1
30.13, 137.92, 143.48, 144.94, 153.63, 155.46, 158.11. HR-MS d6) δ ppm: 14.91, 36.64, 59.02, 107.94, 108.97, 110.03, 111.83,
+
+
(
ESI ) Calcd for C H N O 332.1763. Found 332.1765.
122.32, 123.93, 126.59, 127.34, 128.35, 129.01, 129.36, 137.02,
21
22
3
+
4
-[2-(1-(4-Chlorophenyl)ethylidene)hydrazinyl]-1- 143.36, 144.67, 144.70, 153.39, 154.68, 155.19. HR-MS (ESI )
+
phenethylpyridinium Bromide (2a)
Yield 75%; mp 225°C; IR (KBr) cm : 3399, 3055, 2902,
855, 1645, 1582, 1553, 1539, 1489, 1203, 1176, 1093, 847, 729. phenylpropyl)pyridinium Bromide (3b)
Calcd for C H N O 356.1763. Found 356.1772.
23 22 3
−1
4-[2-(1-(Benzofuran-2-yl)ethylidene)hydrazinyl]-1-(3-
2
1
−1
H-NMR (400MHz, DMSO-d ) δ ppm: 2.43 (3H, s, CH ), 3.16
Yield 60%; mp 77°C; IR (KBr) cm : 3396, 3026, 2991,
6
3
+
(
2H, t, J=7.0Hz, N –CH –CH –Ph), 4.54 (2H, t, J=7.0Hz, 2933, 1641, 1582, 1560, 1533, 1450, 1186, 838, 745, 735.
2
2
+
1
N –CH –CH –Ph), 7.20–7.32 (5H, m, Ar-H), 7.38 (1H, brs,
H-NMR (400MHz, DMSO-d ) δ ppm: 2.18 (2H, quin,
6
2
2
+
pyridinium-H), 7.51 (2H, d, J=8.4Hz, Ar-H), 7.62 (1H, d, J=7.0Hz, N –CH –CH –CH –Ph), 2.52 (3H, s, CH ), 2.64
J=7.2Hz, pyridinium-H), 7.94 (2H, d, J=8.4Hz, Ar-H), 8.34 (2H, t, J=7.0Hz, N –CH –CH –CH –Ph), 4.36 (2H, t,
2
2
+
2
3
2
2
2
13
+
(
2H, brs, pyridinium-H), 11.27 (1H, brs, NH). C-NMR J=7.0Hz, N –CH –CH –CH –Ph), 7.19–7.33 (6H, m, pyridin-
2 2 2
(100MHz, DMSO-d ) δ ppm: 15.22, 36.67, 58.85, 107.91, ium-1H, Ar-5H), 7.42 (1H, td, J=1.2/8.0Hz, benzofuran-H),
6
1
09.84, 127.31, 128.72, 128.91, 128.99, 129.36, 134.87, 136.54, 7.57 (1H, s, benzofuran-H), 7.72–7.74 (4H, m, pyridinium-1H,
+
137.04, 143.26, 144.51, 152.03, 154.88. HR-MS (ESI ) Calcd benzofuran-3H), 8.55 (1H, brs, pyridinium-H), 8.60 (1H, brs,
+
13
for C H ClN 350.1424. Found 350.1431.
pyridinium-H), 11.52 (1H, brs, NH). C-NMR (100MHz,
21
21
3
DMSO-d ) δ ppm: 14.93, 32.03, 32.29, 57.96, 108.25, 108.96,
6
110.30, 111.83, 122.32, 123.93, 126.50, 126.59, 128.36, 128.66,