Abstract
4-Alkylamino-2(1H)-pyridinethiones (1) react with bis-trichlorphenylethylmalonate (3) to give four isomeric products: 5-thioxo-1,6-naphthyridine-2(1H)-ones (4), 7,7-dimethyl-4H-thiopyrano[2,3-b]pyridine-4-ones (6), 2,2-dimethyl-2H-thiopyrano[2,3-b]pyridine-5,7-dioles (7) and 2,2-dimethyl-2H-thiopyrano[2,3-b]pyridine-5(3H)-ones (8). On treatment with alkali the thioxogroup of4 is hydrolyzed and 1,6-naphthyridinediones (5) are formed. Compound5 can also be synthesized by heating the alkylaminopyridones (2) together with3.6 can be hydrolyzed to 2-thioxo-3-pyridylpropylketones (12). On treatment with diluted alkali or conc. acid the aminogroup of7 and8 is hydrolyzed and10 is formed. By heating in 20% NaOH10 is transformed to the dihydroxymercapto-3-pyridylmethylketone (11).
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Ziegler E., Chimia24, 63 (1970).
Zigeuner G., Lintschinger W.-B., Fuchsgruber A., Kollmann K., Mh. Chem.107, 155 (1976).
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Herrn Prof. Dr.Erich Ziegler mit den besten Wünschen zum 70. Geburtstag gewidmet.
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Zigeuner, G., Schweiger, K. & Habernig, D. Zur Reaktion von 4-Alkylaminodihydro-2(1H)-pyridinthionen bzw. -onen mit Ethylmalonsäure-bis-trichlorphenylester. Monatsh Chem 113, 573–581 (1982). https://doi.org/10.1007/BF00800264
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DOI: https://doi.org/10.1007/BF00800264