Nitration of 2-Substituted Pyrimidine-4,6-diones, Structure and Reactivity of 5,5-gem-Dinitropyrimidine-4,6-diones

Nitration of some 2-substituted pyrimidine-4,6-diones in sulfuric acid was studied, which afforded previously unknown 5,5-gem-dinitropyrimidine-4,6-diones in high yields. The gem -dinitro products were easily attacked by nucleophiles with concomitant formation of gem-dinitroacetyl derivatives, which...

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Veröffentlicht in:	Journal of organic chemistry 2002-11, Vol.67 (22), p.7833-7838
Hauptverfasser:	Langlet, Abraham, Latypov, Nikolaj V, Wellmar, Ulf, Bemm, Ulf, Goede, Patrick, Bergman, Jan, Romero, Ivan
Format:	Artikel
Sprache:	eng
Schlagworte:	Aliphatic compounds Chemistry Crystallography, X-Ray Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Hydrolysis Kemi Magnetic Resonance Spectroscopy Medicin och hälsovetenskap Methane Molecular Conformation Molecular Structure NATURAL SCIENCES NATURVETENSKAP Nitrates - chemistry Nitration Organic chemistry Organisk kemi Preparations and properties Pyrimidines - chemical synthesis Pyrimidines - chemistry Substitution reactions Sulfuric acid Temperature Urea Urea - chemistry
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Zusammenfassung:	Nitration of some 2-substituted pyrimidine-4,6-diones in sulfuric acid was studied, which afforded previously unknown 5,5-gem-dinitropyrimidine-4,6-diones in high yields. The gem -dinitro products were easily attacked by nucleophiles with concomitant formation of gem-dinitroacetyl derivatives, which in turn could be further hydrolyzed to salts of dinitromethane and triureas.
ISSN:	0022-3263 1520-6904 1520-6904
DOI:	10.1021/jo025952x