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Synthesis 1992; 1992(10): 969-972
DOI: 10.1055/s-1992-26281
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Oxokohlenstoffe und verwandte Verbindungen;18. Mitteilung1. Umsetzung von Perchlorcyclobutenon mit Pyridinen: Synthese von 4H-4-Chinolizinonen im Eintopfverfahren

Arthur H. Schmidt* , Mario Dümmler
  • *Abteilung für Organische Chemie und Biochemie, Fachhochschule Fresenius, Kapellenstraße 11-15, D-6200 Wiesbaden, Germany
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Publication Date:
17 September 2002 (online)

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Oxocarbons and Related Compounds; Part 18.1 The Reaction of Perchlorocyclobutenone with Pyridines: A Novel Synthesis of 4H-4-Quinolizinones Heating of tetrachlorocyclobutenone (5) with the pyridines 6a-i followed by treatment with water affords 1,3-dichloro-2-hydroxy-4H-4-quinolizinones 7a, b, g-h and 1,3-dichloro-2-hydroxy-4-oxo-4H-quinolizinecarboxylates 7c-f. The reaction pathway has been secured by trapping 1,2,3-trichloro-8-(1,1-dimethylethyl)-4H-4-quinolizinone (11b) and by its successive conversion to 7b on heating with water.