Monatshefte für Chemie / Chemical Monthly

, Volume 112, Issue 10, pp 1211–1219

Ylide von Heterocyclen, III Pyridinium-Ylide von Malonylheterocyclen


  • Thomas Kappe
    • Institut für Organische ChemieUniversität Graz
  • Mehdi Hariri
    • Institut für Organische ChemieUniversität Graz
  • Erik Pongratz
    • Institut für Organische ChemieUniversität Graz
Organische Chemie und biochemie

DOI: 10.1007/BF00905476

Cite this article as:
Kappe, T., Hariri, M. & Pongratz, E. Monatshefte für Chemie (1981) 112: 1211. doi:10.1007/BF00905476

Ylides of heterocycles, III. Pyridinium ylides of malonylheterocycles


Reaction of isatoic anhydride with the betaine esters2 or3 represents a new synthesis of pyridinium ylides of type5, which have been previously obtained by several other ways. Treatment of the ylide5 with inorganic acids results in the formation of their pyridinium salts5 a−d. Hydrogenation or dehydrogenation of5 with Pd/C give the piperidylquinoline9 or the betaine10, respectively. Both of them can be prepared by an alternative way. ThepK values of some pyridinium ylides were determined.


CyclodehydrogenationIsatoic anhydridePalladiumpK ValuesPyridiniummalonate betainePyridinium ylides of quinolinediones

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© Springer-Verlag 1981