Optimization of ultrasound-assisted-one-pot synthesis of 3-substituted-isoindolin-1-onesa.
| ||||
|---|---|---|---|---|
| Entry | [NaBH3CN] (equiv.) | Solvent | Catalyst | Yieldb (%) |
| 1 | 3 | i-PrOH | p-TSA | 63 |
| 2 | 5 | i-PrOH | p-TSA | 70 |
| 3 | 10 | i-PrOH | p-TSA | 86 |
| 4 | 15 | i-PrOH | p-TSA | 75 |
| 5 | 10 | DMSO | p-TSA | 79 |
| 6 | 10 | MeCN | p-TSA | 90 |
| 7 | 10 | THF | p-TSA | 77 |
| 8 | 10 | MeCN | HCl | 72 |
| 9 | 10 | MeCN | TFA | 93 |
| 10 | 10 | MeCN | BF3·OEt2 | 80 |
| 11c | 10 | MeCN | TFA | 77 |
The experiments were performed using 0.5 mmol of 2a and 1.0 mmol of 3a under ultrasonic irradiation (40 kHz, 350 W) for 30 min (1st step) + 60 min (2nd step).
Isolated yields.
The reaction was performed at 50 °C for 5 h + 5 h using conventional heating.