Reaction of β-bromo-β-nitrostyrene 1a with 1,3-diphenylthiourea 2a under different conditions.
| |||||
|---|---|---|---|---|---|
| Entrya | Base | Solvent | Temperature (°C) | Time (h) | Yield (%) |
| 1 | K2CO3 | THF | rt | 24 | 62 |
| 2b | K2CO3 | THF | 70 | 10 | 60 |
| 3 | Et3N | THF | rt | 24 | 72 |
| 4b | Et3N | THF | 70 | 10 | 65 |
| 5 | DBU | THF | rt | 24 | 63 |
| 6b | DBU | THF | 70 | 10 | 58 |
| 7 | KHCO3 | THF | rt | 24 | 55 |
| 8b | KHCO3 | THF | 70 | 10 | 60 |
| 9 | DIPEA | THF | rt | 24 | 68 |
| 10 | None | THF | rt | 24 | 29 |
| 11c | Et3N | THF | rt | 24 | 64 |
| 12d | Et3N | THF | rt | 24 | 58 |
| 13e | Et3N | THF | rt | 24 | 17 |
| 14 | Et3N | CH2Cl2 | rt | 24 | 45 |
| 15 | Et3N | Toluene | rt | 24 | 42 |
| 16b | Et3N | Toluene | 110 | 5 | 40 |
Reactions were performed with β-bromo-β-nitrostyrene 1a (0.10 mmol) and 1,3-diphenylthiourea 2a (0.11 mmol) with base (0.02 mmol) in the indicated solvent (2.0 mL) under atmospheric air.
β-Bromo-β-nitrostyrene was completely consumed.
Reaction was carried out with 0.04 mmol of base.
Reaction was carried out with 0.01 mmol of base.
Reaction was carried out with 0.1 mmol of base.