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1,6‐ and 1,7‐naphthyridines. IV. Synthesis of hydroxycarboxamide derivatives
Author(s) -
Blanco M. Mercedes,
Schapira Celia B.,
Levin Gustavo,
Perillo Isabel A.
Publication year - 2005
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.5570420404
Subject(s) - chemistry , alkoxide , lactam , stereochemistry , proton nmr , carbon 13 nmr , medicinal chemistry , combinatorial chemistry , organic chemistry , catalysis
A series of 8‐hydroxy‐1,6‐naphthyridin‐5(6 H )‐one‐7‐carboxamides 1 and the isomeric 5‐hydroxy‐1,7‐naphthyridin‐8(7 H )‐one‐6‐carboxamides 2 were synthesized. N ‐Lactam unsubstituted compounds 1a‐c and 2a,b were obtained by alkoxide‐induced rearrangement of the corresponding quinolinimidoacetamides 3 . Compounds 1e,f and 2e,f were synthesized by heterocyclization of the corresponding quinolinamic esters 6 and 7 . Spectroscopic properties (uv, ir, 1 H and 13 C nmr and ms) were analyzed and the proposed structures confirmed.