Synthesis of thiophene derivatives 3a–3ja.
| ||||
|---|---|---|---|---|
| Entry | Compd | Ar | R | Yield (%)b |
| 1 | 3a | p-CH3OC6H4 | Bn | 62 |
| 2 | 3b | m-CH3OC6H4 | Bn | 60 |
| 3 | 3c | o-CH3OC6H4 | Bn | 60 |
| 4 | 3d | p-CH3C6H4 | Bn | 55 |
| 5 | 3e | p-ClC6H4 | Bn | 63 |
| 6 | 3f | p-BrC6H4 | Bn | 55 |
| 7 | 3g | p-CH3C6H4 | H | 60 |
| 8 | 3h | p-CH3OC6H4 | Me | 68 |
| 9 | 3i | p-CH3OC6H4 | CH2CH2Ph | 58 |
| 10 | 3j | p-CH3OC6H4 | CH2C6H4OH-p | 66 |
Reaction conditions: 1. ArCHO (2.0 mmol), CH2(CN)2 (2.0 mmol), α-amino acid ethyl ester (2.0 mmol), 1,3-thiazolidinedione (2.0 mmol), Et3N (3.0 mmol), 40–50 °C, 6 h; 2. DDQ (2.2 mmol), 60 °C, 4 h.
Isolated yields.