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Synthese von Pyridonen aus Enaminen und Cyanessigsäuren (1983)

Kappe, Thomas ; Stelzel, Hans Peter ; Ziegler, Erich

Springer

Monatshefte für Chemie 114 (1983), S. 953-963

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ISSN: 1434-4475

Keywords: 2-Amino-4-pyridones ; 4-Hydroxy-2-pyridones ; Ritter-Reaction

Source: Springer Online Journal Archives 1860-2000

Topics: Chemistry and Pharmacology

Notes: Abstract Reaction of enamines1 a–e with cyanoacetic acids2 a,b in acetic anhydride at about 100°C yields the α-cyanoacetylated enamines3 a–g. Under the same conditions methyl 4-cyano-2-(2-pyridyl)-acetoacetate3 h is obtained from methyl 2-pyridylacetate and2 a. Compounds3 are cyclized in hydrochloric acid yielding the 4-hydroxy-2-pyridones4; on the other hand in ethanolic sodium ethoxide solution the 2-amino-4-pyridones are obtained. The esters5 a,b andd are saponified to give the acids7 a–c which decarboxylate at 250°C to8 a–c.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1007/BF00799955

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