Synthesis of podophyllotoxin-naphthoquinone compounds via microwave-assisted three-component reactionsa.
| |||||
|---|---|---|---|---|---|
| Entry | Product | Ar | Time (min) | Yieldb (%) | Mpc (°C) |
| 1 | 5a | 3-OMePh | 15 | 86 | 290–293d |
| 2 | 5b | 3-BrPh | 15 | 83 | 328–329d |
| 3 | 5c | 3-NO2Ph | 15 | 75 | 283–285d |
| 4 | 5d | Ph | 15 | 84 | 329–334d |
| 5 | 5e | 4-MePh | 15 | 88 | 320–322d |
| 6 | 5f | 2-NO2Ph | 15 | 73 | 289–292d |
| 7 | 5g | 3-Oxo-1,3-dihydro benzofuran-5-yl | 15 | 85 | 295–296d |
| 8 | 5h | 2-OHPh | 20 | 80 | 311–312 |
| 9 | 5i | 4-OHPh | 20 | 79 | 304–305 |
| 10 | 5j | 4-NO2Ph | 15 | 82 | 298–299 |
| 11 | 5k | 4-CNPh | 15 | 89 | 306–307 |
| 12 | 5l | 3,4-(MeO)2Ph | 15 | 85 | 288–289 |
| 13 | 5m | 3,4,5-(MeO)3Ph | 15 | 86 | 310–311 |
| 14 | 5n | Pyridin-3-yl | 15 | 81 | 210–212 |
| 15 | 5o | 5-Br-pyridin-2-yl | 15 | 83 | 274–275 |
All the reactions were carried out in 1 mmol scale in 3 mL solvent at 120 °C under MW at the maximum power of 150 W, and the ratio of 6/2/3 was 1/1/1.
Isolated yields.
Decomposed.
These results were reported in our previous study.46