Table 1.
Synthesis of the target 3-nitro-2H-chromenes 5.
| “Synthesis Route” | ||||||
|---|---|---|---|---|---|---|
| ||||||
| Aldehyde | R1 | R2 | Nitrostyrene | R3 | Chromene | Yield |
| 3a | H | H | 4a | H | 5a | 60 |
| 3b | OMe | H | 4a | H | 5b | 67 |
| 3c | Me | H | 4a | H | 5c | 63 |
| 3d | F | H | 4a | H | 5d | 50 |
| 3e | Cl | H | 4a | H | 5e | 40 |
| 3f | Br | H | 4a | H | 5f | 50 |
| 3g | OCF3 | H | 4a | H | 5g | 59 |
| 3h | NO2 | H | 4a | H | - | - |
| 3i | H | OMe | 4a | H | 5h | 65 |
| 3j | H | Me | 4a | H | 5i | 52 |
| 3k | H | OEt | 4a | H | 5j | 66 |
| 3l | tBu | tBu | 4a | H | - | - |
| 3a | H | H | 4b | OMe | 5k | 71 |
| 3a | H | H | 4c | Me | 5l | 40 |
| 3a | H | H | 4d | F | 5m | 82 |
| 3a | H | H | 4e | Cl | 5n | 86 |
| 3a | H | H | 4f | Br | 5o | 95 |
| 3f | Br | H | 4f | Br | 5p | 71 |
| 3e | Cl | H | 4f | Br | 5q | 70 |
| 3m | Br | Br | 4f | Br | 5r | 44 |
| 3n | Br | Cl | 4f | Br | 5s | 51 |
| 3o | Cl | Cl | 4f | Br | 5t | 47 |