Table 1.
1H and 13C NMR spectroscopic data (δ in ppm, J in Hz) for compounds 1–4.
| No | 1 a | 2 a | 3 b | 4 a | ||||
|---|---|---|---|---|---|---|---|---|
| δ H | δ C | δ H | δ C | δ H | δ C | δ H | δ C | |
| 1 | 8.01, d (1.8) | 127.2 | 158.6 | 8.12, d (1.7) | 123.5 | 8.06, d (1.7) | 124.0 | |
| 2 | 145.5 | 138.3 | 149.8 | 149.5 | ||||
| 3 | 7.71, dd (7.9, 1.8) | 135.4 | 7.63, d (7.8) | 133.1 | 7.76, dd (7.9, 1.7) | 131.6 | 7.78, dd (7.9, 1.7) | 131.7 |
| 4 | 8.13, d (7.9) | 127.8 | 7.79, d (7.8) | 118.8 | 8.06, d (7.9) | 126.8 | 8.13, d (7.9) | 126.3 |
| 4 a | 133.5 | 131.8 | 131.7 | 132.1 | ||||
| 5 | 148.4 | 7.54, s | 113.4 | 7.19, s | 109.9 | 157.0 | ||
| 6 | 158.1 | 155.1 | 157.0 | 139.8 | ||||
| 7 | 7.38, d (8.5) | 121.6 | 153.5 | 139.6 | 160.3 | |||
| 8 | 8.04, d (8.5) | 125.8 | 7.44, s | 108.8 | 159.2 | 7.16, s | 110.5 | |
| 8 a | 127.9 | 125.2 | 109.6 | 129.3 | ||||
| 9 | 182.6 | 187.8 | 186.1 | 181.9 | ||||
| 9 a | 133.7 | 115.2 | 133.2 | 132.9 | ||||
| 10 | 182.7 | 181.8 | 181.4 | 185.5 | ||||
| 10 a | 127.5 | 129.2 | 129.1 | 109.0 | ||||
| 2-Me | 2.53, s | 21.6 | ||||||
| 2-CH2OH | 4.62, s | 57.9 | 4.67, s | 62.2 | 4.66, s | 62.2 | ||
| 5-OMe | 3.95, s | 61.7 | ||||||
| 6-OMe | 3.82, s | 59.8 | ||||||
| 7-OMe | 3.95, s | 56.3 | 3.83, s | 59.9 | ||||
a 1H at 400 MHz and 13C at 150 MHz in Acetone-d6. b 1H at 400 MHz and 13C at 150 MHz in DMSO-d6.