Research Article
Preparation and Antibacterial Activity of Some New 4-(2-Heterylidenehydrazinyl)-7-chloroquinoline Derivatives
Table 2
1H, 13C-NMR, and HR-MS spectral data of compounds 4a–c.
| | Number | X = H (4a) | X = CH3 (4b) | X = OC2H5 (4c) | | (ppm)
J (Hz) | (ppm) | (ppm)
J (Hz) | (ppm) | (ppm)
J (Hz) | (ppm) | |
| | 2 | 8.68 (d)
J = 4.5 | 152.5 | 8.67 (d)
J = 5.0 | 152.0 | 8.67 (d)
J = 4.5 | 157.3 | | | 3 | 7.62 (d)
J = 5.0 | 102.9 | 7.60 (d)
J = 5.5 | 101.8 | 7.58 (d)
J = 4.5 | 101.8 | | 4 | - | 149.2 | - | 149.2 | - | 150.0 | | 5 | 8.42 (d)
J = 9.0 | 124.2 | 8.42 (d)
J = 9.0 | 123.8 | 8.40 (d)
J = 9.0 | 123.8 | | 6 | 7.67 (dd)
= 8.5; = 1.5 | 124.3 | 7.66 (dd)
= 9.0; = 2.0 | 125.3 | 7.65 (d)
J = 8.5 | 124.2 | | 7 | - | 133.4 | - | 133.9 | - | 133.7 | | 8 | 7.96 (br) | 128.1 | 7.96 (d)
J = 2.5 | 127.4 | 7.95 (br) | 127.8 | | 9 | - | 147.3 | - | 145.5 | - | 145.9 | | 10 | - | 116.1 | - | 115.6 | - | 115.3 | | 11 | 11.70 (s) | - | 11.67 (s) | - | 11.67 (s) | - | | 13 | 8.85 (s) | 138.5 | 8.83 (s) | 138.1 | 8.80 (s) | 139.0 | | 14 | - | 125.8 | - | 126.5 | - | 125.3 | | 15 | - | 127.1 | - | 127.1 | - | 127.5 | | 17 | - | 137.8 | - | 137.5 | - | 138.1 | | 18 | 8.23 (d)
J = 8.5 | 127.6 | 7.89 (d)
J = 8.5 | 127.3 | 7.87 (d)
J = 9.5 | 128.4 | | 19 | 7.72 (t)
J = 8.0 | 131.9 | 7.70 (dd)
= 8.5; = 1.5 | 133.6 | 7.46 (dd)
= 9.0; = 2.5 | 130.0 | | 20 | 7.86 (t)
J = 7.5 | 148.8 | - | 146.6 | - | 145.6 | | 20a | - | - | 2.54 (s) | 21.2 | 4.21 (q)
J = 7.0 | 63.7 | | 20b | - | - | - | - | 1.44 (t)
J = 7.0 | 14.5 | | 21 | 7.99 (d)
J = 8.5 | 129.2 | 7.99 (s) | 127.8 | 7.61 (s) | 129.1 | | 22 | - | 148.3 | - | 147.4 | - | 142.8 | | 23 | 9.15 (s) | 134.6 | 9.02 (s) | 134.3 | 9.01 (s) | 134.7 | | MS | 367.0518 [M + H]+
(C19H13Cl2N4 + H, 367.0512) | 381.0674 [M + H]+
(C20H15Cl2N4 + H, 381.0668) | 411.0775 [M + H]+
(C21H17Cl2N4O + H, 411.0774) |
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More information can be found in Supplementary Materials.
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