Nitration of 2-substituted pyrimidine-4, 6-diones, structure and reactivity of 5, 5-gem-dinitropyrimidine-4, 6-diones

…, U Bemm, P Goede, J Bergman, I Romero

Index: Langlet, Abraham; Latypov, Nikolaj V.; Wellmar, Ulf; Bemm, Ulf; Goede, Patrick; Bergman, Jan; Romero, Ivan Journal of Organic Chemistry, 2002 , vol. 67, # 22 p. 7833 - 7838

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Citation Number: 14

Abstract

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.