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Synthesis of novel 1,7‐naphthyridines by Friedländer condensation of pyridine substrates
Author(s) -
Stockmann Vegar,
Fiksdahl Anne
Publication year - 2011
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.657
Subject(s) - chemistry , condensation , nitration , ketone , pyridine , yield (engineering) , aldehyde , methyl ketone , aryl , dimer , substrate (aquarium) , medicinal chemistry , organic chemistry , catalysis , physics , materials science , alkyl , oceanography , metallurgy , thermodynamics , geology
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).