2.7- Naphthyridine reactions

For a detailed account of naphthyridine reactions with nitrogen nucleophiles, see chapter by van der Plas et al., p. 95 of this volume. 

Hermecz and co-workers used the Hantzsch 1,4-dihydropyridine synthesis in their preparation of naphthyridines. Reaction of ethyl acetoacetate 8 and hexamethylenetetramine 221 as a novel source of nitrogen... 

The antibacterial agent nalidixic acid [389-08-2] (37) is formed by reaction of 2-ainino-6-methylpyridine [1824-81 -3] with an alkoxymethylenemalonic ester to form the 1,8-naphthyridine carboxyUc ester followed by alkylation and ester hydrolysis (37). 

Naphth[2,l-d]oxazolium iodide, 2,3-dimethyl-reactions, 6, 215 Naphthyridine, amino-reactions, 2, 598 Naphthyridine, N-amino-reactions, 2, 596 Naphthyridine, 3-bromo-reactions... 

Quino[3,2-c][l,8]naphthyridine — see 4,5,12-Triazabenz[a]anthracenes Quinone, a-tocopheryl-synthesis, 3, 734 o-Quinone allides synthesis, 3, 741 o-Quinone diazides reactions... 

The 2,7-naphthyridine system 53 (Scheme 8.4.18) was combined with 2,4-dinitrochlorobenzene and 2-amino glycerol for in situ reaction of the resulting Zincke salt. The resulting naphthyridinium 54 was trapped by Bradsher cycloaddition with (Z)-vinyl ether 55, providing tetracycle 56 (X-ray) upon internal addition of one of the diastereotopic hydroxymethyl groups to the resulting iminium. This approach was also extended to the use of chiral 2,7-naphthyridinium salts, prepared via the analogous Zincke process. ... 

Shortly after Gabriel and Colman reported cinchomeronylacetic ester, Pels reported a similar quinolinimidoacetic ester (40) to provide a 1,6-naphthyridine (41).The structure of the isolated compound was not unambiguously determined for more than 30 years.More recently, the reaction has been shown to produce both 41 and 42 in a 3 1 ratio... 

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