Table 2.
One-Pot Optimization Toward Fluorescent Pyrido-imidazo[4,5-c]isoquinolines
| ||||
|---|---|---|---|---|
| Entrya | Acid (eq.) | Solvent (0.3 M) | Time (min) | Yield (%) |
| 1 | Cu(OTf)2(1.0) | MeOH | 5 | 0 |
| 2 | Cu(OTf)2(1.0) | DCMb | 20 | 0 |
| 3 | Cu(OTf)2(1.0) | ACN | 20 | 0 |
| 4 | - | AcOH | 20 | 28 |
| 5 | H2SO4(30 eq.) | AcOH | 20 | 6 |
| 6 | H2SO4(50 eq.) | MeOH | 20 | 0 |
| 7 | H2SO4(50 eq.) | MeOH | 20, 5c | 81 |
| 8 | H2SO4(50 eq.) | MeOH | 20, 10c | 87 |
| 9 | H2SO4(50 eq.) | MeOH | 20, 20c | 96 |
Scale: 1.0 mmol
100 °C
Acid was added after 1st indicated time and set to run for the 2nd indicated time at 140 °C (microwave irradiation).