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. 2019 Dec 3;9(68):40072–40083. doi: 10.1039/c9ra07653k

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
graphic file with name c9ra07653k-u1.jpg
a

Pyrone 1 (1.11 mmol) and amine 2 (1.11 mmol) were stirred in EtOH (6 mL) at 0 °C for 1 h.

b

The reaction was performed at 20 °C for 2 h.

c

The reaction was performed at 20 °C for 4 days, 2.22 mmol of the amine was used.