1,6-Naphthyridine → 1,6-naphthyridin-5(6H)-one

Participants

Reaction Steps

Reaction Scheme V illustrates the preparation of 1,6-naphthyridin-5(6H)-one compounds. In the initial condensation of N-Boc-protected 2-chloro-4-amino-nicotinaldehyde with the (substituted phenyl)benzyl ketone (V-1) in the presence of an alkoxide, such as, sodium methoxide, there is obtained directly the 1,6-naphthyridine (V-2) substituted at the 5-position with the alkoxide group. Acid catalyzed hydrolysis readily converts the 1,6-naphthyridine to the requisite 1,6-naphthyridin-5(6H)-one aldehyde functionality (V-3) and this material can undergo reductive amination with a diverse array of amines to give the 1,6-naphthyridin-5(6H)-one compounds (V-6).

Provenance & Evidence