Table 1.
1H-NMR data (300 MHz, CDCl3) for 3–6, 8, 10–15.
| Position | δH (ppm); J (Hz) | ||||
|---|---|---|---|---|---|
| 3 | 4 | 5 | 6 | 8 | |
| H-2 | 6.68, s | 6.62, s | - | - | 7.74, s |
| H-5 | 7.57, dd (8.6, 1.1) |
6.84–6.77, m | 7.52, dd (8.6, 1.1, 0.5) |
7.52, d (2.4) |
6.97–6.92, m |
| H-6 | 7.78, ddd (8.6, 7.1, 1.8) |
- | 7.70, ddd (8.6, 7.1, 1.7) |
- | - |
| H-7 | 7.40, ddd (8.0, 7.1, 1.1) |
6.84–6.77, m | 7.37, ddd (8.1, 7.1, 1.1) |
6.94, dd (8.8, 2.4) |
6.97–6.92, m |
| H-8 | 8.11, dd (8.0, 1.8) |
7.93, d (9.1) |
8.27, ddd (8.1, 1.7, 0.5) |
8.18, d (8.8) |
8.20, d (7.9, 1.3) |
| 1-CH3 | 2.68, s | 2.65, s | 3.05, s | 3.06, s | - |
| 3-OH | 10.34, s | - | - | - | - |
| 4-OH | 9.18, s | - | - | - | - |
| 6-OH | - | - | - | - | - |
| 3-OCH3 | - | - | 4.04, s | 4.06, s | 4.10, s |
| 4-OCH3 | - | - | 4.07, s | 4.03, s | 4.04, s |
| 6-OCH3 | - | - | - | 3.94, s | 3.95, s |
| H-1′ | - | - | - | - | 8.98, s |
| CHO | - | - | - | - | - |
| COOCH3 | - | - | - | - | - |
| NOH | - | - | - | - | - |
| 10 | 12 | 13 | 14 | 15 | |
| H-2 | 7.52, s | 8.40, s | 6.99, s | 6.98–6.90, m | 7.43, s |
| H-5 | 6.99–6.94, m | 6.89–7.10, m | 7.59, d (7.5) | 6.98–6.90, m | 7.67, brdd (7.9) |
| H-6 | - | - | 7.75, ddd (8.8, 7.1, 1.7) | - | 7.85, ddd, (7.5, 5.8, 1.7) |
| H-7 | 6.99–6.94, m | 6.89–7.10, m | 7.40, ddd (8.1, 7.2, 1.1) | 6.98–6.90, m | 7.46, ddd (8.0, 7.5, 1.0) |
| H-8 | 8.20, d (9.4) | 8.31, d (8.8) | 8.28, dd (8.8, 1.7) | 8.17, d (8.8) | 8.14, dd (7.9, 1.5) |
| 1-CH3 | - | - | - | - | - |
| 3-OH | - | - | - | - | - |
| 4-OH | - | - | - | - | - |
| 6-OH | - | - | - | - | - |
| 3-OCH3 | 4.05, s, | 4.12, s | 4.04, s | 4.03, s | 3.99, s |
| 4-OCH3 | 4.09, s | 4.10, s | 4.06, s | 4.00, s | 3.94, s |
| 6-OCH3 | 3.95, s | 3.99, s | - | 3.93, s | - |
| H-1′ | - | - | - | - | 9.31, s |
| CHO | 11.23, s | - | - | - | - |
| COOCH3 | - | - | - | 4.03, s | - |
| NOH | - | - | - | - | 11.44, s |