The synthesis of pyridine derivatives (1a–15a) catalyzed by ETG-acetamidea.
| |||||||
|---|---|---|---|---|---|---|---|
| Entry | R | Ketone | Product | Time (h) | Yielda (%) | Mp. (°C) | Ref. |
| 1a | H |
|
|
3 | 71b | 242–244 | 237–239 (ref. 44) |
| 2a | 4-OMe |
|
|
3 | 47b | 239–240 | 234–236 (ref. 45) |
| 3a | 4-Cl |
|
|
3 | 33b | 266–268 | 260–261 (ref. 45) |
| 4a | 4-F |
|
|
3.5 | 58b | 259–260 | — |
| 5a | 2-Cl |
|
|
3 | 46b | 259–261 | 254–257 (ref. 46) |
| 6a | 2-F |
|
|
3 | 44b | 254–256 | — |
| 7a | 4-Br |
|
|
3 | 53b | 299–301 | 255–257 (ref. 45) |
| 8a | 4-Me |
|
|
3 | 44b | 258–260 | 256–258 (ref. 46) |
| 9a | Furfural |
|
|
3 | 48b | 216–218 | — |
| 10a | H |
|
|
2.5 | 15c | 186–187 | 185–187 (ref. 47) |
| 11a | 4-OMe |
|
|
2.5 | 12c | 188–190 | 192–195 (ref. 48) |
| 12a | 4-Cl |
|
|
3 | 46c | 185–186 | 203–205 (ref. 49) |
| 13a | 4-F |
|
|
3 | 19c | 164–166 | 164–166 (ref. 50) |
| 14a | 4-Br |
|
|
3 | 36c | 183–185 | 186–188 (ref. 50) |
| 15a | 4-Me |
|
|
3 | 31c | 210–212 | 215–217 (ref. 49) |
| 231–233 (ref. 51) | |||||||
Reaction conditions: arylaldehyde (1 mmol), malononitrile (1 mmol), cyclohexanone/dimedone (1 mmol), ammonium acetate (1.5 mmol), ETG-acetamide (50 mg) at 80 °C.
Isolated yield by crystallization in ethanol (10–15 mL).
Isolated yield via column chromatography (n-hexane : EtOAc = 5 : 5).