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Paper | Regular issue | Vol 51, No. 9, 1999, pp.2119-2126
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8614
Novel Dipolar and Tripolar Betaines: Synthesis, Ring-Cleavage, Spectroscopic Features, and X-Ray Analysis of a Positively Charged Pyrimidin-4-olate

Andreas Schmidt* and Martin Nieger

*Ernst-Moritz-Arndt-Universität Greifswald, Institut für Chemie und Biochemie, Soldmannstrasse 16, D-17487 Greifswald, Germany

Abstract

Reaction of tetrachioropyrimidine (1) with pyridine resulted in the formation of a heteroaromatic tripole, the 2,6-bispyridiniopyrimidin-4-olate chloride (3), the structure of which was established by X-Ray crystallography. Amberlite® IRA-400 in its hydroxy form converted 3 into the corresponding stable hydroxide (4), which undergoes ring-cleavage on titration with sodium hydroxide to pH 9. Thus, the 5-aminopenta-2,4-dienal appended mesomeric betaine (5) formed.