Synthesis of 1,6-diamino-4-aryl-2-oxo-1,2-dihydropyridine-3,5-dicarbonitrile 4a–la.
Entry | Aromatic aldehyde | Product | Time (h) | Yield (%) | M.p. (°C) |
---|---|---|---|---|---|
1 | 12 | 93 | 340 (dec.)41 | ||
2 | 12 | 88 | 355 (dec.) | ||
3 | 12 | 91 | 360 (dec.)41 | ||
4 | 16 | 83 | 321–323 (ref. 41) | ||
5 | 15 | 85 | 265–267 | ||
6 | 12 | 90 | 332–334 (ref. 41) | ||
7 | 11 | 87 | 305–307 (ref. 41) | ||
8 | 12 | 85 | 292–294 | ||
9 | 13 | 80 | 365 (dec.) | ||
10 | 17 | 75 | 290–292 (ref. 41) | ||
11 | 11 | 83 | 338–340 | ||
12 | 13 | 78 | 324–326 |
All reactions were carried out with cyanoacetohydrazide 1 (1 mmol), malononitrile 2a (1 mmol), aromatic aldehydes 3 (1 mmol) and piperidine (0.02 mmol) in water (10 ml).