Table 3.
1H NMR (500 MHz) data of the benzamides 1–5 in DMSO-d6, δ in ppm relative to TMS, multiplicities (J/Hz).
| Position | Anthra. (1) a) | Pyram. A (2) a,b) | Pyram. B (3) a) | Pyram. C (4) a) | Pyram. D (5) a) |
|---|---|---|---|---|---|
|
| |||||
| δH (J/Hz) | δH (J/Hz) | δH (J/Hz) | δH (J/Hz) | δH (J/Hz) | |
| 1-CONH2 | 7.70 (1H, br s), 7.03 (1H, br s) | 8.21 (1H, br s), 7.68 (1H, br s) | 8.29 (1H, br s), 7.63 (1H, br s) | 8.16 (1H, br s), 7.59 (1H, br s) | 8.30 (1H, br s), 7.78 (1H, br s) |
| 2-OH | - | 13.40 (1H, br s) | 13.49 (1H, br s) | 13.0-11.0 (1H, br s) | 13.52 (1H, br s) |
| 2-NH2 | 6.54 (2H, br s) | - | - | - | - |
| 3 | 6.66 (1H, dd, 8.5, 1.0) | 6.39 (1H, d, 2.5) | - | - | - |
| 3-NH | - | - | - | - | 8.87 (1H, br s) |
| 3-NH2 | - | - | - | 13.0-11.0 (2H, br s) | - |
| 3-OCH3 | - | - | 3.68 (3H, s) | - | - |
| 3-NHCOCH3 | - | - | - | - | 1.96 (3H, s) |
| 4 | 7.12 (1H, td, 7.0, 1.5) | - | - | - | - |
| 4-OH | - | - | 9.86 (1H, br s) | - | - |
| 4-OCH3 | - | 3.75 (3H, s) | - | 3.79 (3H, s) | 3.80 (3H, s) |
| 5 | 6.47 (1H, td, 8.0, 1.0) | 6.43 (1H, dd, 9.0, 2.5) | 6.33 (1H, d, 8.5) | 6.47 (d, 9.0) | 6.58 (d, 8.5) |
| 6 | 7.51 (1H, dd, 8.0, 1.5) | 7.76 (1H, d, 9.0) | 7.43 (1H, d, 9.0) | 7.16 (d, 9.0) | 7.77 (d, 9.0) |
a)
See also Figures S5–8, S12–22, S24–27, S31–S34, S36–39 and S43–47 for comparison;
b)
For 1H NMR data in CDCl3, see the experimental part.