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. 2023 Aug 22;13(36):25054–25068. doi: 10.1039/d3ra04558g

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
a

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).

b

Isolated yields of 3 and 4.