Effects of reagent and solvent on the reaction of 1-(4-(chloromethyl)benzyl)-5-methylindoline-2,3-dione, isatin, malononitrile and 1,3-cyclohexanedion under different conditionsa.
| Entry | Reagent | reagent (mmol) | Solvent | Temp. (°C) | Time (h) | Yield (%) |
|---|---|---|---|---|---|---|
| 1 | — | — | PEG-400 | r.t. | 48 | — |
| 2 | l-Proline | 1.0 | PEG-400 | r.t. | 48 | — |
| 3 | DABCO | 1.0 | PEG-400 | r.t. | 48 | — |
| 4 | Et3N | 1.0 | PEG-400 | r.t. | 48 | — |
| 5 | Cs2CO3 | 1.0 | PEG-400 | r.t. | 24 | 65 |
| 6 | Na2CO3 | 1.0 | PEG-400 | r.t. | 24 | 30 |
| 7 | NaHCO3 | 1.0 | PEG-400 | r.t. | 24 | — |
| 8 | CaCO3 | 1.0 | PEG-400 | r.t. | 24 | 25 |
| 9 | K2CO3 | 1.0 | PEG-400 | r.t. | 7 | 95 |
| 10 | K2CO3 | 0.5 | PEG-400 | r.t. | 15 | 70 |
| 11 | K2CO3 | 0.8 | PEG-400 | r.t. | 15 | 87 |
| 12 | K2CO3 | 1.5 | PEG-400 | r.t. | 7 | 94 |
| 13 | K2CO3 | 1.0 | MeCN | r.t. | 48 | Trace |
| 14 | K2CO3 | 1.0 | H2O | r.t. | 48 | — |
| 15 | K2CO3 | 1.0 | EtOH | r.t. | 48 | — |
| 16 | K2CO3 | 1.0 | MeOH | r.t. | 24 | — |
| 17 | K2CO3 | 1.0 | n-Propanol | r.t. | 24 | — |
| 18 | K2CO3 | 1.0 | tert-Butanol | r.t. | 24 | — |
| 19 | K2CO3 | 1.0 | DMSO | r.t. | 13 | 80 |
| 20 | K2CO3 | 1.0 | DMF | r.t. | 15 | 80 |
| 21 | K2CO3 | 1.0 | — | 80 | 48 | — |
| 22 | K2CO3 | 1.0 | — | 100 | 48 | — |
a
Isolated yields.