Synthesis of some 1-alkyl-1,4-dihydro-4-oxo-1,7-naphthyridine-3-carboxylic acids

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Title:Synthesis of some 1-alkyl-1,4-dihydro-4-oxo-1,7-naphthyridine-3-carboxylic acids
Creators:
Rádl, Stanislav
Hradil, Pavel
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 56, 11, pp. 2420-2429

Abstract

Reaction of substituted 2-aminopyridines <i>IIIa, IIIb, IIIe</i>, and <i>IIIf</i> with ethyl ethoxymethylene malonate provided corresponding pyridylaminomethylenemalonates <i>Va-Vd</i>, respectively. Thermal cyclization of <i>Va, Vc</i>, and <i>Vd</i> yielded substituted ethyl 4-hydroxy-1,7-naphthyridine-3-carboxylates <i>VIa, VIc</i>, and <i>VId</i>. Compounds <i>VIc</i> and <i>VId</i> treated with morpholine gave 8-morpholino derivatives <i>VIe</i> and <i>VIf</i>. These compounds were ethylated to mixtures of N-ethylated (<i>VIIa, VIIb</i>) and O-ethylated products (<i>VIIIa, VIIIb</i>). Compound <i>VIIIb</i> was also prepared from ethyl 4-chloro-6-fluoro-8-morpholino-1,7-naphthyridine-3-carboxylate <i>VIIIc</i> and sodium ethanolate. Esters <i>VIIa</i> and <i>VIIb</i> were hydrolyzed under acidic conditions to the respective acids <i>VIIc</i> and <i>VIId</i>.

Title:Synthesis of some 1-alkyl-1,4-dihydro-4-oxo-1,7-naphthyridine-3-carboxylic acids
Creators:
Rádl, Stanislav
Hradil, Pavel
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:56
Number:11
Page Range:pp. 2420-2429
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19912420UNSPECIFIED
ID Code:5173
Item Type:Article
Deposited On:22 Feb 2010 11:32
Last Modified:22 Feb 2010 10:32

Citation

Rádl, Stanislav; Hradil, Pavel (1991) Synthesis of some 1-alkyl-1,4-dihydro-4-oxo-1,7-naphthyridine-3-carboxylic acids. Collection of Czechoslovak Chemical Communications, 56 (11). pp. 2420-2429. ISSN 0010-0765

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