Vol. 67, No. 11 (2019)
Chem. Pharm. Bull.
1197
of reactions (as indicated by TLC [TLC system: chloroform/ 55.3, 55.2, 111.0, 115.3, 115.4, 118.0, 120.0, 121.1, 129.7, 130.1,
ethanol (90:10)]. Contents were then poured in crushed ice 131.2, 131.4, 131.9, 132.0, 136.7, 137.4, 137.6, 145.3, 147.8,
and were neutralized with aqueous sodium hydroxide solution 148.4, 155.4, 159.8, 161.8, 163.3, 176.4. MS EI, m/z: [M]+
(0.1M). Precipitated products were then filtered, washed with 545.4, [M+ +2] 547.4. Anal. Calcd for C28H25BrN4O3: C, 61.66;
ethanol (30%) followed by crystallization from chloroform.
H, 4.62; N, 10.27. Found: C, 61.61; H, 4.65; N, 10.23.
N′-(3-(4-Chlorophenyl)-1-phenylallylidene)-1-ethyl-7-
N′-(1-(4-Chlorophenyl)-3-(2-fluorophenyl)allylidene)-1-
methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carbohydrazide ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-
(7a)
carbohydrazide (7e)
Pale yellow crystals; mp 241–243°C; IR (KBr) cm−1: 3041,
Pale powder; mp 254–256°C; IR (KBr) cm−1: 3032,
1633, 1605; 1H-NMR: (CDCl3, 300MHz) δ: 1.46 (3H, t, 1665,1604; 1H-NMR (CDCl3, 300MHz) δ: 1.51 (3H, t,
J=7.1Hz, CH3), 2.63 (3H, s, CH3), 4.51 (2H, q, J=7.2Hz, J=14.4Hz, CH3), 2.68 (3H, s, CH3), 4.60 (2H, d, J=7.0Hz,
CH2), 6.34 (1H, d, J=16.2Hz, CH), 7.17 (1H, d, J=8.1Hz, CH2), 6.59 (1H, d, J=16.5Hz, CH), 7.15(1H, d, J=7.5,
CH), 7.28 (1H, d, J=8.2Hz, CH), 7.34–7.65 (9H, m, ArH), CH), 7.35(1H, d, J=8.1, CH), 7.40–7.93 (8H, m, ArH), 8.52
8.44 (1H, d, J=8.2Hz, CH), 8.94 (1H, s, CH), 12.63 (1H, (1H, d, J=8.1Hz, CH), 8.98 (1H, s, CH), 12.76 (1H, s, NH);
s, NH); 13C-NMR: (75MHz, CDCl3) δ: 15.3, 25.1, 103.1, 13C-NMR (CDCl3) δ: 15.2, 25.1, 46.9, 112.0, 115.8, 116.4,
120.9, 122.5, 128.2, 128.3, 128.4, 128.6, 128.9, 129.2, 129.4, 120.0, 121.1,124.3, 127.2, 128.4, 128.9, 129.5, 129.8, 129.9,
129.5, 129.7, 130.3, 132.9, 136.7, 138.1, 140.4, 143.3, 147.8, 130.7, 131.3, 132.0, 136.7, 138, 147.8, 148.3, 155.4, 158.7, 161.8,
150.7, 152.9, 157.7, 160.9, 161.4, 174.9. MS electron ioniza- 163.3, 176.4. MS EI, m/z: [M]+ 488.9, [M+ +2] 490.9. Anal.
tion (EI), m/z: [M]+ 470.9, [M+ +2] 472.9. Anal. Calcd for Calcd for C27H22ClFN4O2: C, 66.32; H, 4.54; N, 11.46. Found:
C27H23ClN4O2: C, 68.86; H, 4.97; N, 11.91. Found: C, 68.71; H, C, 66.25; H, 4.51; N, 11.4.
4.93; N, 11.82.
N′-(3-(2,4-Dichlorophenyl)-1-(4-iodophenyl)allylidene)-1-
N′-(3-(4-Chlorophenyl)-1-(4-methoxyphenyl)allylidene)-1- ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-
ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3- carbohydrazide (7f)
carbohydrazide (7b)
Off white powder; mp 258–260°C; IR (KBr) cm−1: 3050,
Yellow crystals; mp 248–249°C; IR (KBr) cm−1: 3042, 1658, 1674,1607; 1H-NMR (CDCl3, 300MHz) δ: 1.47 (3H, t,
1
1609; H-NMR (CDCl3,300MHz) δ: 1.46 (3H, t, J=7.1Hz, J=7.1Hz, CH3), 2.65 (3H, s, CH3), 4.56 (2H, q, J=7.2Hz,
CH3), 2.63 (3H, s, CH3), 3.94 (3H, s, CH3), 4.51 (2H, q, CH2), 6.73 (1H, d, J=16.4Hz, CH), 7.13 (1H, d, J=8.4Hz,
J=7.2Hz, CH2), 6.36 (1H, d, J=16.4Hz, CH), 7.19 (1H, d, CH), 7.34 (1H, d, J=6.9Hz, CH), 7.21–8.11 (7H, m, ArH),
J=8.1Hz, CH), 7.31 (1H, d, J=5.7Hz, CH), 7.48–7.10 (8H, 8.49 (1H, d, J=8.2Hz, CH), 8.93 (1H, s, CH), 12.81 (1H,
m, ArH), 8.47 (1H, d, J=8.0Hz, CH), 8.94 (1H, s, CH), 12.6 s, NH); 13C-NMR (CDCl3) δ: 15.2, 25.1,46.9, 100.9, 121.2,
(1H, s, NH); 13C-NMR (CDCl3) δ: 15.2, 25.1, 46.9, 55.5, 55.3, 124.4, 127.4, 127.5, 128.5, 129.5, 129.7, 129.9, 130.0, 130.9,
114.9, 120.0, 121, 122.3, 129.1, 129.2, 129.4, 129.8, 130.7, 133.6, 131.2, 132.1, 132.2, 136.7, 138.2, 138.8, 139.8, 147.9, 147.8,
134.1, 135.1, 135.8, 136.1, 136.5, 136.7, 142.4, 147.8, 148.4, 154.9, 161.9, 163.4, 189.3. MS EI, m/z: [M]+ 631.2, [M+ +2]
156.3, 161.7, 163.2,176.4. MS EI, m/z: [M]+ 500.9, [M+ +2] 633.2, [M+ +4]635.2, [M+ +6] 637.2. Anal. Calcd for
502.9. Anal. Calcd for C28H25ClN4O3: C, 67.13; H, 5.03; N, C27H21Cl2IN4O2: C, 51.37; H, 3.35; N, 8.87. Found: C, 51.43; H,
11.18. Found: C, 66.93; H, 5.06; N, 11.10.
3.33; N, 8.84.
N′-(3-(4-Bromophenyl)-1-(4-methoxyphenyl)allylidene)-1-
N′-(1-(4-Chlorophenyl)-3-(4-methoxyphenyl)allylidene)-1-
ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3- ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-
carbohydrazide (7c)
carbohydrazide (7g)
Pale crystals; mp 245–246°C; IR (KBr) cm−1: 3043, 1653,
White powder; mp 254–256°C; IR (KBr) cm−1: 3016, 1681,
1
1
1611; H-NMR (CDCl3, 300MHz) δ: 1.47 (3H, t, J=7.0Hz, 1616; H-NMR (CDCl3, 300MHz) δ: 1.46 (3H, t, J=14.1Hz,
CH3), 2.64 (3H, s, CH3), 3.98 (3H, s, CH3), 4.52 (2H, q, CH3), 2.64 (3H, s, CH3), 3.79 (3H, s, CH3), 4.56 (2H, q,
J=7.1Hz, CH2), 6.36 (1H, d, J=16.2Hz, CH), 7.17 (1H, d, J=7.2Hz, CH2), 6.36 (1H, d, J=16.2Hz, CH), 7.21 (1H, d,
J=6.3Hz, CH), 7.29 (1H, d, J=8.7Hz, CH), 7.14–7.54 (8H, J=8.1Hz, CH), 7.32 (1H, d, J=10.5Hz, CH), 7.40–7.69 (8H,
m, ArH), 8.47 (1H, d, J=8.1Hz, CH), 8.94 (1H, s, CH), 12.71 m, ArH), 8.48 (1H, d, J=8.1Hz, CH), 8.93 (1H, s, CH), 12.67
(1H, s, NH); 13C-NMR (75MHz, CDCl3) δ: 15.2, 25.1, 46.9, (1H, s, NH); 13C-NMR (CDCl3) δ: 15.2, 25.1, 46.9, 55.3, 55.4,
55.3, 55.5, 104.1, 113.9, 114.9, 121.2, 121.6, 122.4, 128.4, 128.7, 114.2, 114.4, 119.1, 121.1, 128.5, 128.7, 128.8, 129.0, 129.1,
129.7, 129.8, 130.8, 130.9, 131.8, 132.0, 132.1, 134.0, 135.9, 129.3, 129.4, 129.6, 129.7, 129.8, 130.3, 136.7, 145.2, 147.7,
136.7, 142.4, 147.8,160.7, 163.2, 178.1. MS EI, m/z: [M]+ 545.4, 157.4, 161.7, 161.8, 163.2, 176.4. MS EI, m/z: [M]+ 500.9,
[M+ +2] 547.4. Anal. Calcd for C28H25BrN4O3: C, 61.66; H, [M+ +2] 502.9. Anal. Calcd for C28H25ClN4O3: C, 67.13; H,
4.62; N, 10.27. Found: C, 61.6; H, 4.65; N, 10.23.
5.03; N, 11.18. Found: C, 66.97; H, 5.05; N, 11.13.
N′-(1-(4-Bromophenyl)-3-(3-methoxyphenyl)allylidene)-1-
N′-(3-(2-Chlorophenyl)-1-phenylallylidene)-1-ethyl-7-
ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3- methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carbohydrazide
carbohydrazide (7d)
(7h)
White powder; mp 246–247°C; IR (KBr) cm−1: 3104, 1678,
Yellow crystals; mp 252–254°C; IR (KBr) cm−1: 3024, 1668,
1
1
1610; H-NMR (CDCl3, 300MHz) : δ1.47(3H, t, J=14.1Hz, 1611; H-NMR (CDCl3, 300MHz) δ: 1.45 (3H, t, J=7.1Hz,
CH3), 2.67 (3H, s, CH3), 3.79 (3H, s, CH3), 4.55 (2H, q, CH3), 2.63 (3H, s, CH3), 4.52 (2H, q, J=7.2Hz, CH2), 6.34
J=7.1Hz, CH2), 6.34 (1H, d, J=16.2Hz, CH), 6.95 (1H, d, (1H, d, J=16.2Hz, CH), 7.16 (1H, d, J=8.1Hz, CH), 7.28
J=6.3Hz, CH), 7.31 (1H, d, J=8.4Hz, CH), 7.18–7.79 (8H, (1H, d, J=8.2Hz, CH), 7.32–7.61 (9H, m, ArH), 8.44 (1H,
m, ArH), 8.49 (1H, d, J=8.2Hz, CH), 8.94 (1H, s, CH), 12.70 d, J=8.2Hz, CH), 8.94 (1H, s, CH), 12.61 (1H, s, NH);
(1H, s, NH); 13C-NMR (75MHz CDCl3) δ: 15.2, 25.1, 46.9, 13C-NMR (CDCl3) δ: 15.2, 25.1, 48.1, 106.1, 120.9, 122.4,