| Autor: |
Schweiger, Klaus, Habernig, Dietmar, Schramm, Hans-Wolfgang, Zigeuner, Gustav |
| Zdroj: |
Chemical Monthly / Monatshefte für Chemie; 1983, Vol. 114 Issue 1, p79-88, 10p |
| Abstrakt: |
4-Alkylaminopyridinethiones · HCl ( 1 · HCl) react with bis-trichlorethylmalonate ( 3) predominantly to 5-alkylamino-4 H-thiopyrano [2,3-b]pyridine-4-ones ( 6). With alcohols in the presence of acids at 25°C 6 undergoes an alcoholysis to the corresponding alkyl-3-(2-thioxo-3-pyridyl)propionates ( 9). On heating in dilute alkali 6 is hydrolysed via 4-alkylamino-2-thioxopyridyl-propylketones ( 11) to the tautomers, 4-hydroxy-2-thioxopyridylpropylketone ( 12 A) and 2-thioxo-3-(1-hydroxybutenyl)-4-piperidon ( 12 B), resp. On refluxing with alkali the ethyl-pyridylpropionate 9 a is cyclisized to the 1-alkyl-1,6-naphthyridine-2(1 H)-one ( 4 a), but boiling in ethanolic acid hydrolyses 9 a via the pyridylpropionic acid 10 to 4-alkyl-aminopyridylpropylketone ( 11 a). The latter can be transformed via the tautomers 12 A, B and 2-methylthio-3-pyridylpropylketone ( 13) to the 4-hydroxy-3-butyrylpyridone ( 14 A) and its tautomer, 3-(1-hydroxy-butenyl)-piperidine-2,4-diones ( 14 B) resp. The structure of 14 A, B is established by reaction of 4-isopropylamino-2(1 H)-pyridone ( 2) with butanoylchloride to the 4-isopropylamino-3-butyrypyridone ( 15) and hydrolysis of 15 to the tautomers 14 A, B. [ABSTRACT FROM AUTHOR] |
| Databáze: |
Complementary Index |
| Externí odkaz: |
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