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. 2018 Jul 30;8(48):27131–27143. doi: 10.1039/c8ra05690k

Synthesis of 1,6-diamino-4-aryl-2-oxo-1,2-dihydropyridine-3,5-dicarbonitrile 4a–la.

graphic file with name c8ra05690k-u1.jpg
Entry Aromatic aldehyde Product Time (h) Yield (%) M.p. (°C)
1 graphic file with name c8ra05690k-u2.jpg graphic file with name c8ra05690k-u3.jpg 12 93 340 (dec.)41
2 graphic file with name c8ra05690k-u4.jpg graphic file with name c8ra05690k-u5.jpg 12 88 355 (dec.)
3 graphic file with name c8ra05690k-u6.jpg graphic file with name c8ra05690k-u7.jpg 12 91 360 (dec.)41
4 graphic file with name c8ra05690k-u8.jpg graphic file with name c8ra05690k-u9.jpg 16 83 321–323 (ref. 41)
5 graphic file with name c8ra05690k-u10.jpg graphic file with name c8ra05690k-u11.jpg 15 85 265–267
6 graphic file with name c8ra05690k-u12.jpg graphic file with name c8ra05690k-u13.jpg 12 90 332–334 (ref. 41)
7 graphic file with name c8ra05690k-u14.jpg graphic file with name c8ra05690k-u15.jpg 11 87 305–307 (ref. 41)
8 graphic file with name c8ra05690k-u16.jpg graphic file with name c8ra05690k-u17.jpg 12 85 292–294
9 graphic file with name c8ra05690k-u18.jpg graphic file with name c8ra05690k-u19.jpg 13 80 365 (dec.)
10 graphic file with name c8ra05690k-u20.jpg graphic file with name c8ra05690k-u21.jpg 17 75 290–292 (ref. 41)
11 graphic file with name c8ra05690k-u22.jpg graphic file with name c8ra05690k-u23.jpg 11 83 338–340
12 graphic file with name c8ra05690k-u24.jpg graphic file with name c8ra05690k-u25.jpg 13 78 324–326
a

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).