4-Amino-1,2-dihydropyridin-2-one → 4-(3-Acetyl-2-methyl-5-oxo-1,4,5,6-tetrahydro-1,6-naphthyridin-4-yl)-3-ethylbenzonitrile

Participants

Reaction Steps

1 g (4.14 mmol) of 4-(2-acetyl-3-oxobut-1-en-1-yl)-3-ethylbenzonitrile and 0.45 g (4.14 mmol) of 4-aminopyridin-2(1H)-one [Scats, T., McLaughlin, L. W., Tetrahedron 55, 11985-11996 (1999)] are dissolved in 20 ml of isopropanol and stirred at the reflux temperature under argon for 4 days. The mixture is then concentrated and the residue is purified by column chromatography on silica gel (mobile phase: dichloromethane/methanol 10:1). 277 mg (20% of theory) of the title compound are obtained as a pale yellow solid.

Provenance & Evidence