Table 10. Selected optimization condition for xanthene derivativesa.
| |||||
|---|---|---|---|---|---|
| Entry | Catalyst (mol%) | Solvent | Temp. (°C) | Timeb (min) | Yieldc (%) |
| 1 | 1 | MeOH | 70 | 60 | 35 |
| 2 | 1 | Water | 70 | 60 | 20 |
| 3 | 1 | ACN | 70 | 60 | 50 |
| 4 | 1 | IPA | 70 | 60 | 98 |
| 5 | 1 | THF | 70 | 60 | 40 |
| 6 | 1 | CH2Cl2 | 70 | 60 | 30 |
| 7 | 1 | MeOH | 80 | 80 | 40 |
| 8 | 1 | ACN | 80 | 80 | 60 |
| 9 | 1 | IPA | 80 | 80 | 98 |
| 10 | 1 | THF | 80 | 80 | 50 |
| 11 | 1 | CH2Cl2 | 80 | 80 | 40 |
| 12 | 1 | IPA | 25 | 90 | — |
| 13 | 0.5 | IPA | 70 | 60 | 60 |
| 14 | 2 | IPA | 70 | 60 | 85 |
| 15 | — | IPA | 70 | 180 | 10 |
Reaction condition: benzaldehyde (1 mmol), dimedone (2 mmol).
Reaction progress monitored by TLC.
Isolated yield.