A Simple Synthesis of Stable 1,4-Diionic Pyridinium Betaines

Summary.

 Protonation of the reactive intermediate produced in the reaction between pyridine and dialkyl acetylenedicarboxylates by strong CH-acids such as N,N′-dimethylbarbituric acid, Meldrum’s acid, or indane-1,3-dione leads to a vinylpyridinium cation which undergoes an addition reaction with the enolate anion of the CH-acid to produce stable 1,4-diionic pyridinium betaines in good yields.