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Nitration of 2-substituted pyrimidine-4,6-diones, structure and reactivity of 5,5-gem-dinitropyrimidine-4,6-diones
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2002 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 67, no 22, 7833-7838 p.Article in journal (Refereed) Published
Abstract [en]

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.

Place, publisher, year, edition, pages
2002. Vol. 67, no 22, 7833-7838 p.
Keyword [en]
Hydrolysis, Methane, Molecular structure, Nitration, Substitution reactions, Sulfuric acid, Urea
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-9034DOI: 10.1021/jo025952xISI: 000178820200035PubMedID: 12398510OAI: oai:DiVA.org:kth-9034DiVA: diva2:14574
Note
Tidigare titel: Nitration of 2-Substituted Pyrimidine-4,6-diones, Structure and Reactivity of 5,5-gem-Dinitropyrimidine QC 20100907Available from: 2006-01-26 Created: 2006-01-26 Last updated: 2010-09-07Bibliographically approved
In thesis
1. Nitration of Oxo-pyramidines and Oxo-imidazoles
Open this publication in new window or tab >>Nitration of Oxo-pyramidines and Oxo-imidazoles
2006 (English)Doctoral thesis, comprehensive summary (Other scientific)
Abstract [en]

This thesis is mainly focused on the reactions of oxo-pyrimidines and oxo-imidazoles with nitric acid in sulfuric acid and properties of the gem-dinitro products formed in this process.

Low temperature nitrations of 2-methylimidazoles produced – in addition to the known 2-methyl-5(4)-nitroimidazole – 2-(dinitromethylene)-5,5-dinitro-4-imidazolidinone and parabanic acid. This tetranitro compound was also obtained via nitration of 2-methyl-4,4-dihydro-(1H)-5- imidazolone. Thermal decomposition of 2-(dinitromethylene)-5,5-dinitro-4-imidazolidinone yielded 2-(dinitromethylene)-4,5-imidazolidinedione, which also was the product from the nitration of the new compound 2-methoxy-2-methyl-4,5-imidazolidienedione. Treatment of 2- (dinitromethylene)-5,5-dinitro-4-imidazolidinone with aqueous ammonia resulted in the previously unknown 1,1-diamino-2,2-dinitroethylene (Paper I).

The nitration of some 2-substituted pyrimidine-4,6-diones in sulfuric acid, which afforded previously unknown 5,5-gem-dinitro-pyrimidine-4,6-diones in high yields, was studied. Alloxane was prepared in a one-step procedure by thermal decomposition of 5,5-dinitrobarbituric acid in hot acetic acid. The gem-dinitro products were found to be easily attacked by nucleophiles with concomitant formation of gem-dinitroacetyl derivatives, which in turn could be further hydrolysed to salts of dinitromethane and triureas (Papers II and III).

Nitration of 4,6-dihydroxypyrimidine in sulfuric acid yielded nitroform as the sole product. This behaviour was tentatively explained by the formation of an intermediate, 5,5-dinitro-4,6- dihydroxypyrimidine, which underwent hydrolysis in the nitrating acid into gem-dinitroacetyl formamidine. This compound was further nitrated in the same reaction mixture into trinitroacetylformamidine, which finally underwent hydrolytic cleavage into nitroform. It was also demonstrated that gem-dinitroacetylureas could produce nitroform upon nitration. The structures of the proposed trinitroacetylureas were confirmed by the isolation of one of their derivatives (Paper IV).

Place, publisher, year, edition, pages
Stockholm: KTH, 2006. 34 p.
Keyword
explosives, gem-Dinitro compounds, Dinitromethane, Nitroform
National Category
Organic Chemistry
Identifiers
urn:nbn:se:kth:diva-601 (URN)91-7178-255-9 (ISBN)
Public defence
2006-02-10, Sal K2, Teknikringen 28, Stockholm, 10:00
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Note
QC 20100907Available from: 2006-01-26 Created: 2006-01-26 Last updated: 2010-09-07Bibliographically approved

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