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Ethyl 1,4‐Dihydro‐4‐oxo‐1,8‐naphthyridine‐3‐carboxylates by a Tandem S N Ar‐Addition‐Elimination Reaction
Author(s) -
Bunce Richard A.,
Nammalwar Baskar
Publication year - 2012
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.917
Subject(s) - chemistry , yield (engineering) , dimethylformamide , tandem , derivative (finance) , medicinal chemistry , carboxylate , acetal , reaction conditions , primary (astronomy) , cascade reaction , organic chemistry , catalysis , materials science , solvent , financial economics , metallurgy , composite material , physics , astronomy , economics
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 120 o C for 24 h then afforded the target compounds in 47–82% yields by a tandem S N Ar‐addition‐elimination reaction. Synthetic and procedural details as well as a mechanistic rationale are presented.
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