Ammonia → HCID 15336554, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2 (1.96 g, 10 mmol), methyl propiolate (1.68 g, 20 mmol), and 40 mL of ammonia-saturated methanol in a 300 mL stainless steel Parr reaction vessel was heated to 150° C. for 6 h. After cooling, the solvent was removed under reduced pressure, and the crude product was purified by flash chromatography with 3% MeOH in CH2Cl2 as the eluent to afford 2.96 g (60%) of the pyridone 3: Rf =0.40 (10% MeOH in CH2Cl2); IR (KBr) 3448, 2887, 1649, 1618, 1093 cm-1 ; 1H NMR δ6.38 (d, 1H, J=9.3 Hz), 5.75 (m, 1H), 5.11 (m, 2H), 3.97 (m, 3H), 3.10 (m, 1H), 2.70 (m, 4H), 1.85 (m, 2H); 13C NMR δ164.7, 143.9, 143.2, 118.1, 118.0, 111.8, 107.4, 64.6, 64.4, 37.6, 36.8, 35.8, 34.8.

Provenance & Evidence