Monatshefte für Chemie / Chemical Monthly

, Volume 119, Issue 8–9, pp 985–992 | Cite as

Zur Ringumwandlung von 2-Amino-thiophen-3-carbonsäureestern: Pyridon- und Pyridazinon-Derivate

  • Karl Gewald
  • Margit Gruner
  • Ute Hain
  • Gabriele Süptitz
Organische Chemie Und Biochemie

Ringtransformation of ethyl 2-amino-thiophene-3-carboxylates: Derivatives of pyridones and pyridazinones

Abstract

Whereas treatment of the ethyl 5-acetyl-2-amino-4-methyl-thiophene-3-carboxylate (1) with potassium hydroxide yields the 2-hydroxy-thiophene-3-carbonitrile4 its hydrazone2 is converted into the 1-amino-5-mercapto-2-pyridone derivative6. The transformation of the 2-amino-5-phenylazo-thiophene derivative9 by potassium hydroxide yields the substituted 3-mercapto-pyridazin-6(1H)one10, with sodium ethoxide the 5-phenylhydrazono-2-oxo-thiolen-3-carbonitrile11 is formed. From6 the 5-mercapto-2-pyridone derivatives7 d,e can be obtained.

Keywords

2-Aminothiophene-3-carboxylic acid derivatives 1-Amino-2-pyridone 1,2-Dihydro-2-oxo-pyridine-5-thioles Pyridazin-6(1H)-one 

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Literatur

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    Gewald K, Jablokoff H, Hentschel M (1975) J Prakt Chem 317: 861Google Scholar
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    Tieckelmann (1974) In:Abramovitch RA (Hrsg) The chemistry of heterocyclic compounds, vol 14, suppl 3. Wiley, New York, S 839 und dort angegebene LiteraturGoogle Scholar
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Copyright information

© Springer-Verlag 1988

Authors and Affiliations

  • Karl Gewald
    • 1
  • Margit Gruner
    • 1
  • Ute Hain
    • 1
  • Gabriele Süptitz
    • 1
  1. 1.Sektion ChemieTechnische Universität DresdenDresdenDeutsche Demokratische Republik

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