220729-16-8Relevant academic research and scientific papers
Ethyl 1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylates by a tandem S NAr-addition-elimination reaction
Bunce, Richard A.,Nammalwar, Baskar
experimental part, p. 658 - 663 (2012/08/27)
A series of N-substituted 1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate esters has been prepared in two steps from ethyl 2-(2-chloronicotinoyl)acetate. Treatment of the β-ketoester with N,N-dimethylformamide dimethyl acetal in N,N-dimethylformamide (DMF) gave a 95% yield of the 2-dimethylaminomethylene derivative. Subsequent reaction of this β-enaminone with primary amines in DMF at 120oC for 24 h then afforded the target compounds in 47-82% yields by a tandem SNAr-addition-elimination reaction. Synthetic and procedural details as well as a mechanistic rationale are presented.
