Diaminomethyleneaminocarbonyldinitromethane, formed during the preparation of 2-amino-6-chloro-5-nitro-4(3H)-pyrimidinone by nitration of 2-amino-6-chloro-4(3H)-pyrimidinone
“…This particular finding, summarized in Scheme , and compounds 3a , c and 4a , c were first presented by us in June 2000 . Half of a year later Boyle et al described an analogous nitration of 2-amino-4,6-(3 H ,5 H )-pyrimidinedione ( 1a ) and 2-amino-6-chloro-4(3 H )-pyrimidinone, as well as compound 4a , without mentioning our original work . Instead of mixed acids these authors used solutions of potassium nitrate in sulfuric acid, claiming that the latter system ensured a more easily controlled course of nitration and higher yields of gem -dinitrated products.…”
Section: Discussionmentioning
confidence: 99%
“…At elevated temperatures an additional peak at ca. 8.1 ppm appears, which probably originates from the anion of dinitromethane ( 6 ) , produced by partial hydrolysis of the substance. 2 Partial variable-temperature 300-MHz 1 H NMR spectra recorded in DMSO- d 6 .…”
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.
“…This particular finding, summarized in Scheme , and compounds 3a , c and 4a , c were first presented by us in June 2000 . Half of a year later Boyle et al described an analogous nitration of 2-amino-4,6-(3 H ,5 H )-pyrimidinedione ( 1a ) and 2-amino-6-chloro-4(3 H )-pyrimidinone, as well as compound 4a , without mentioning our original work . Instead of mixed acids these authors used solutions of potassium nitrate in sulfuric acid, claiming that the latter system ensured a more easily controlled course of nitration and higher yields of gem -dinitrated products.…”
Section: Discussionmentioning
confidence: 99%
“…At elevated temperatures an additional peak at ca. 8.1 ppm appears, which probably originates from the anion of dinitromethane ( 6 ) , produced by partial hydrolysis of the substance. 2 Partial variable-temperature 300-MHz 1 H NMR spectra recorded in DMSO- d 6 .…”
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.
“…Thus, we decided to introduce the nitro group initially into 2-amino-4-hydroxypyrimidin-6-one (2). This nitration has been well documented and under carefully controlled conditions (potassium nitrate in sulfuric acid), 10 the required 5-nitro compound 3 can be obtained in high yield (Scheme 1).…”
“…Use of potassium nitrate in sulfuric acid gives the desired 2-amino-6-chloro-5-nitro-4(3H)pyrimidone 2 in 72% yield. 15 The nitration of 6-substituted purine nucleosides with tetrabutylammonium nitrate and trifluoroacetic anhydride proceeds to give the 2-nitrated products. The method is limited to those substrates which do not possess NH or OH substituents.…”
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