DBU-catalyzed tandem annulation of arylhydrazonopropanals 1a–o with acetoacetanilide 2 under conventional and microwave conditionsa.
| Entry | Products | R | Ar | Thermal (2 h) | MW (3 min) | ||
|---|---|---|---|---|---|---|---|
| Yieldb | Yieldb | ||||||
| 3 | 4 | 3 | 4 | ||||
| 1 | 3a/4a | 4-NO2C6H4 | 4-BrC6H4 | 84 | 10 | 95 | Trace |
| 2 | 3b/4b | 4-NO2C6H4 | 4-ClC6H4 | 80 | 13 | 93 | Trace |
| 3 | 3c/4c | 4-NO2C6H4 | 3-ClC6H4 | 78 | 16 | 90 | Trace |
| 4 | 3d/4d | 4-NO2C6H4 | C6H5 | 72 | 20 | 83 | 10 |
| 5 | 3e/4e | 4-ClC6H4 | C6H5 | 62 | 28 | 70 | 22 |
| 6 | 3f/4f | 4-ClC6H4 | 4-BrC6H4 | 74 | 18 | 86 | 8 |
| 7 | 3g/4g | 4-BrC6H4 | 4-ClC6H4 | 66 | 25 | 75 | 16 |
| 8 | 3h/4h | 4-BrC6H4 | 4-BrC6H4 | 67 | 25 | 75 | 18 |
| 9 | 3i/4i | 4-FC6H4 | 4-ClC6H4 | 75 | 18 | 88 | Trace |
| 10 | 3j/4j | 4-FC6H4 | 4-BrC6H4 | 76 | 18 | 88 | Trace |
| 11 | 3k/4k | 4-OMeC6H4 | 4-BrC6H4 | 52 | 38 | 60 | 28 |
| 12 | 3l/4l | 4-OMeC6H4 | o-NO2C6H4 | 55 | 35 | 64 | 24 |
| 13 | 3m/4m | C6H5 | 4-ClC6H4 | 62 | 27 | 70 | 20 |
| 14 | 3n/4n | C6H5 | 4-BrC6H4 | 60 | 30 | 70 | 18 |
| 15 | 3o/4o | C6H5 | o-NO2C6H4 | 70 | 20 | 83 | 10 |
Reaction condition: 1a–o (0.5 mmol), acetoacetanilide 2 (0.5 mmol), DBU (0.3 mmol) in 1,4-dioxane (6 mL), at 40 °C for 2 h (thermal heating), and 40 °C (200 W) for 3 min (microwave irradiation).
Isolated yields of 3 and 4.