
doi: 10.1002/jhet.657
AbstractThe general ability of appropriate pyridyl compounds (aldehyde or ketone) to undergo Friedländer condensation to give different 1,7‐naphthyridines has been demonstrated. 2,4‐Disubstituted 1,7‐naphthyridine 8 was prepared from 3‐amino‐4‐acetylpyridine (6) and ketone 4 (82%). The Friedländer self‐condensation of pyridyl substrate 6 is reported, as well. The dimer product, 2‐(3‐aminopyridin‐4‐yl)‐4‐methyl‐1,7‐naphthyridine (7), was obtained in 97% yield. 2‐Aryl‐ and 2,3‐diaryl‐1,7‐naphthyridines (16, 17, 18) were prepared from 3‐aminoisonicotinaldehyde (13) and arylketones 4, 14, and 15 (28–71%). The key substrates 6 and 13 are readily available via the improved pyridine nitration method. J. Heterocyclic Chem., (2011).
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