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Paper | Regular issue | Vol 43, No. 10, 1996, pp.2153-2167
Published online, 1st January, 1970
DOI: 10.3987/COM-96-7529
Novel Barbituric Acid Derivatives, Uracil-pyridinium Salts and Polycondensed Oxopyrimidines

Andreas Schmidt, Annemarie Hetzheim, and Dirk Albrecht

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


Nucleophilic substitution of the 6-chloropyrimidines (1) with piperodine, morpholine, 4-(piperidin-1-yl)piperidine and 4-dimethylaminopyridine yielded the corresponding 6-aminosubstituted pyrimidines (2), (3), (4), and (5), respectively. The barbiturates (9) and (10) were formed either starting from the chloroaldehyde (7), or by applying Knovenagel reaction to the barbituric acid (13) with 2-formylaminohetarenes. Cyclocondensation of the chloroldehyde (11) with 2-aminnopyrisines resulted in the formation of the tricycle (12) which is also sccessible by initial Knoevenagel reaction of the barbituric acid (14) and subsequent cyclization of the resulting barbiturates (15). Analogously, the new ring system (17) was formed upon treatment of 14 with 2-formylaminopyrimidine and subsequent cyclization.