Table 2.
Preparation of 1,8-dioxodecahydroacridine derivatives using NiO@Bentonite nanocomposite as catalyst.
| Entrya | R (aldehyde) | Product | Time (min) | Yield (%)b | ||
|---|---|---|---|---|---|---|
| Found | Reported [ref.] | |||||
| 1 | 3-NO2C6H4- | 4a | 3 | 97 | 193–196 | 194–19654 |
| 2 | 3-OCH3-4OHC6H3 | 4b | 2 | 94 | 221–225 | 224–22655 |
| 3 | 4-ClC6H4- | 4c | 5 | 92 | 148–149 | 148–15154 |
| 4 | 4-OHC6H4- | 4d | 3 | 95 | 282–284 | 284–28640 |
| 5 | 4-OCH3C6H4- | 4e | 3 | 98 | 217–218 | 219–22154 |
| 6 | 5-Br-2-OHC6H3- | 4f | 10 | 98 | 247–251 | 248–25050 |
| 7 | 2-OH-1-naphthaldehyde | 4g | 12 | 99 | 288–290 | New |
| 8 | 2-NO2C6H4- | 4h | 4 | 97 | 188–190 | 187–18942 |
| 9 | 4-N(CH3)2C6H4- | 4i | 2 | 99 | 168–170 | 166–16842 |
| 10 | 2-OH-3-OCH3C6H3- | 4j | 2 | 94 | 228–229 | 227–23054 |
| 11 | 4-BrC6H4- | 4k | 6 | 98 | > 300 | > 30040 |
| 12 | 3-OHC6H4- | 4l | 4 | 94 | 231–233 | 230–23242 |
| 13 | 2-ClC6H4- | 4m | 4 | 92 | 248–250 | 249–25256 |
| 14 | 3,4,5-(OCH3)3C6H2- | 4n | 2 | 95 | 222–224 | New |
aReaction conditions: 3-nitrobenzaldehyde (4 mmol), aniline (4 mmol), dimedone (8 mmol) and NiO@Bentonite catalyst (0.121 g, 20% wt.) under different conditions.
bIsolated yields after purification.