Table 1 Optimization of the reaction conditions for the Hantzsch condensation of para-Chlorobenzaldehyde, dimedone, ethyl acetoacetate, and ammonium acetate as the model reaction for the synthesis of polyhydroquinolines.
Entry | Catalyst | Amount Catalyst (mg) | Solvent | Temperature (°C) | Time (min) | Yield (%)a,b |
|---|---|---|---|---|---|---|
1 | – | – | PEG-400 | 80 | 85 | 30 |
2 | 4,6-Diamino-2-pyrimidinethiol | 10 | PEG-400 | 80 | 85 | 41 |
3 | Zn(NO3)2.6H2O | 10 | PEG-400 | 80 | 85 | 30 |
4 | Zn-MOF | 5 | PEG-400 | 80 | 85 | 75 |
5 | Zn-MOF | 6 | PEG-400 | 80 | 85 | 79 |
6 | Zn-MOF | 10 | PEG-400 | 80 | 85 | 96 |
7 | Zn-MOF | 12 | PEG-400 | 80 | 85 | 92 |
8 | Zn-MOF | 10 | EtOH | 80 | 195 | 83 |
9 | Zn-MOF | 10 | H2O | 80 | 120 | N.R |
10 | Zn-MOF | 10 | DMF | 80 | 210 | 60 |
11 | Zn-MOF | 10 | DMSO | 80 | 95 | 70 |
12 | Zn-MOF | 10 | PEG-400 | 25 | 120 | N.R |
13 | Zn-MOF | 10 | PEG-400 | 60 | 85 | 21 |
14 | Zn-MOF | 10 | PEG-400 | 100 | 85 | 44 |
