Reaction scope study of pyrones 1 with amines 2a.
| Adduct | Pyrone | Amine | R | X | Yield, % | E-3 : Z-3 : keto-E-3 |
|---|---|---|---|---|---|---|
| 3a | 1a | 2a | Ph | H | 87 | 82 : 13 : 5 |
| 3b | 1b | 2a | 4-MeOC6H4 | H | 85 | 95 : 2 : 3 |
| 3c | 1a | 2b | Ph | OH | 68 | 76 : 17 : 7 |
| 3d | 1c | 2b | 4-ClC6H4 | OH | 81 | 76 : 17 : 7 |
| 3e | 1b | 2c | 4-MeOC6H4 | NH2 | 86 | 79 : 15 : 6 |
| 3f | 1c | 2c | 4-ClC6H4 | NH2 | 78 | 78 : 16 : 6 |
| 3g | 1d | 2c | 2-Naph | NH2 | 90 | 79 : 13 : 8 |
| 3h | 1e | 2c | 2-Th | NH2 | 90 | 89 : 8 : 3 |
| 3i | 1f | 2c | t-Bu | NH2 | 61 | 79 : 14 : 7 |
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Pyrone 1 (1.11 mmol) and amine 2 (1.11 mmol) were stirred in EtOH (6 mL) at 0 °C for 1 h.
The reaction was performed at 20 °C for 2 h.
The reaction was performed at 20 °C for 4 days, 2.22 mmol of the amine was used.