Table 4. Selected optimization conditions for the synthesis of chromene derivativesa.
| |||||
|---|---|---|---|---|---|
| Entry | Catalyst (mol%) | Solvent | Temp. (°C) | Timeb (min) | Yieldc (%) |
| 1 | 1 | MeOH | 25 | 5 | 40 |
| 2 | 1 | Water | 25 | 5 | 25 |
| 3 | 1 | ACN | 25 | 5 | 90 |
| 4 | 1 | EtOH | 25 | 5 | 92 |
| 5 | 1 | Ethanol–water | 25 | 5 | 60 |
| 6 | 1 | THF | 25 | 5 | 45 |
| 7 | 1 | CH2Cl2 | 25 | 5 | 30 |
| 8 | 1 | MeOH | 25 | 10 | 40 |
| 9 | 1 | ACN | 25 | 10 | 80 |
| 10 | 1 | EtOH | 25 | 10 | 92 |
| 11 | 1 | Ethanol–water | 25 | 10 | 45 |
| 12 | 1 | THF | 25 | 10 | 50 |
| 13 | 1 | CH2Cl2 | 25 | 10 | 40 |
| 14 | 1 | EtOH | 50 | 30 | 92 |
| 15 | 0.5 | EtOH | 25 | 30 | 85 |
| 16 | 2 | EtOH | 25 | 30 | 80 |
| 17 | — | EtOH | 25 | 180 | 30 |
| 18 | — | EtOH | 50 | 240 | 30 |
Reaction condition: benzaldehyde (1 mmol), malononitrile (1 mmol).
Reaction progress monitored by TLC.
Isolated yield.