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Zur Synthese von 4-Aminochinolinen durch intramolekulareFriedel—Crafts-Reaktion

The synthesis of 4-amino-quinolines by intramolecular Friedel—Crafts Reaction

  • Organische Chemie und Biochemie
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Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Abstract

Treatment of arylaminomethylene-malononitriles,-cyanoacetamides and-ω-cyanoacetophenones with AlCl3 yields substituted 4-aminoquinolines2, while quinolin-4-ones3 are obtained from ethyl arylaminomethylene cyanoacetates. N-β-naphthylcyanoacetamide reacts in the presence of AlCl3 to form 1-amino-3-benzo[f]quinolinone (6). Isothiazolo[4,3−c]quinolines (10) and pyrimido[5,4−c]quinolines (11, 12) can be obtained from2. 4-Aminoquinoline-3-carboxylic acids derived from2, can be decarboxylated.3 are cyclized to form oxazino[5,6−c]-quinolinones (4).

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Authors and Affiliations

  1. Sektion Chemie, Technische Universität Dresden, DDR-8027, Dresden, Deutsche Demokratische Republik

    Harry Schäfer & Karl Gewald

Authors
  1. Harry Schäfer
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  2. Karl Gewald
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Schäfer, H., Gewald, K. Zur Synthese von 4-Aminochinolinen durch intramolekulareFriedel—Crafts-Reaktion. Monatshefte für Chemie 109, 527–535 (1978). https://doi.org/10.1007/BF00912769

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  • DOI: https://doi.org/10.1007/BF00912769

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