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Synthesis of novel 1,7-naphthyridines by Friedländer condensation of pyridine substrates

✍ Scribed by Vegar Stockmann; Anne Fiksdahl

Publisher
Journal of Heterocyclic Chemistry
Year
2011
Tongue
English
Weight
299 KB
Volume
48
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

The 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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