1,6 and 1,7-Naphthyridines. I. Rearrangement of Quinolinimidoacetic acid Derivatives

BLANCO, M. LORENZO, M. G., PERILLO, I. Y SCHAPIRA, C

JOURNAL OF HETEROCYCLIC CHEMISTRY

Año: 1996 vol. 33 p. 361 - 366

0022-152X

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 1H-nmr spectra with those of picolinamide and nicotinamide. When esters 1a-c were treated with alkoxides from primary alcohols, others than that of the ester, total transesterification took place. Experimental results suggest that transesterification occurs in open intermediary species.