Organische Chemie und biochemie

Monatshefte für Chemie / Chemical Monthly

, Volume 112, Issue 10, pp 1211-1219

First online:

Ylide von Heterocyclen, III Pyridinium-Ylide von Malonylheterocyclen

  • Thomas KappeAffiliated withInstitut für Organische Chemie, Universität Graz
  • , Mehdi HaririAffiliated withInstitut für Organische Chemie, Universität Graz
  • , Erik PongratzAffiliated withInstitut für Organische Chemie, Universität Graz

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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.


Cyclodehydrogenation Isatoic anhydride Palladium pK Values Pyridiniummalonate betaine Pyridinium ylides of quinolinediones