Substrate scope of 1 and synthesis of target molecules 3a.
| ||||
|---|---|---|---|---|
| Entry | 1 (R/R1) | 2 (R2) | 3 | Yieldb (%) |
| 1 | 1a (4-FC6H5/CH3) | 2a (4-ClC6H5) | 3a | 66 |
| 2 | 1a (4-FC6H5/CH3) | 2b (C6H5) | 3b | 58 |
| 3 | 1b (3-FC6H5/CH3) | 2b (C6H5) | 3c | 62 |
| 4 | 1c (3-ClC6H5/CH3) | 2a (4-ClC6H5) | 3d | 63 |
| 5 | 1c (3-ClC6H5/CH3) | 2b (C6H5) | 3e | 68 |
| 6 | 1d (4-BrC6H5/CH3) | 2a (4-ClC6H5) | 3f | 65 |
| 7 | 1d (4-BrC6H5/CH3) | 2b (C6H5) | 3g | 62 |
| 8 | 1e (3-BrC6H5/CH3) | 2b (C6H5) | 3h | 60 |
| 9 | 1f (C6H5/CH3) | 2a (4-ClC6H5) | 3i | 65 |
| 10 | 1f (C6H5/CH3) | 2b (C6H5) | 3j | 63 |
| 11 | 1f (C6H5/CH3) | 2c (4-OCH3C6H5) | 3k | 64 |
| 12 | 1g (3-CH3C6H5/CH3) | 2b (C6H5) | 3l | 62 |
| 13 | 1h (n-butyl/CH3) | 2a (4-ClC6H5) | 3m | 70 |
| 14 | 1i (4-ClC6H5/H) | 2a (4-ClC6H5) | 3n | 71 |
| 15 | 1j (3-ClC6H5/H) | 2a (4-ClC6H5) | 3o | 72 |
| 16 | 1k (3-BrC6H5/H) | 2c (4-OCH3C6H5) | 3p | 68 |
| 17 | 1l (4-CH3C6H5/H) | 2a (4-ClC6H5) | 3q | 60 |
| 18 | 1a (4-FC6H5/CH3) | 2d (n-propyl) | 3r | 62 |
The reaction was performed with 1 (1.0 mmol), 2 (0.6 mmol), and p-TSA (0.3 mmol) in EtOH (15 mL) at reflux for 3 hours.
Isolated yields based on enaminones 1.