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Synthesis and reaction of 5,5-dinitrobarbituric acid
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2000 (English)In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Tetrahedron letters, Vol. 41, no 12, 2011-2013 p.Article in journal (Refereed) Published
Abstract [en]

Nitration of barbituric acid at 40°C gave the previously unknown 5,5- dinitrobarbituric acid (3), which readily underwent hydrolysis to dinitroacetylurea (5), which in turn could be hydrolysed in basic media to the potassium salt of dinitromethane. Alloxane was prepared in a one step procedure by thermal decomposition of 5,5-dinitrobarbituric acid in hot acetic acid.

Place, publisher, year, edition, pages
2000. Vol. 41, no 12, 2011-2013 p.
Keyword [en]
Nitration, Nitro compounds, Nitrogen heterocycles
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-9035DOI: 10.1016/S0040-4039(00)00086-1ISI: 000086086100036OAI: oai:DiVA.org:kth-9035DiVA: diva2:14575
Note
QC 20100907Available from: 2006-01-26 Created: 2006-01-26 Last updated: 2017-12-14Bibliographically 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
Opponent
Supervisors
Note
QC 20100907Available from: 2006-01-26 Created: 2006-01-26 Last updated: 2010-09-07Bibliographically approved

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