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1,6‐ and 1,7‐naphthyridines. I. Rearrangement of quinolinimidoacetic acid derivatives
Author(s) -
Blanco Mercedes,
Lorenzo M. Gabriela,
Perillo Isabel,
Schapira Celia B.
Publication year - 1996
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.5570330226
Subject(s) - chemistry , transesterification , nicotinamide , sodium salt , sodium , organic chemistry , medicinal chemistry , catalysis , inorganic chemistry , enzyme
The reaction of N ‐substituted quinolinimides 1a‐d with sodium alkoxides afforded a mixture of 1,6‐naphthyridines 2 and 1,7‐naphthyridines 3 which were isolated by chromatographic methods. Structure assignment for each pair of isomers was made by comparison of their 1 H nmr spectra with those of picolinamide and nicotinamide. When esters 1a ‐c were treated with alkoxides from primary alcohols, other than that of the ester, total transesterification took place. Experimental results suggest that transesterification occurs in open intermediary species.