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 in turn could be further hydrolyzed to salts of dinitromethane and triureas.
Langlet
Abraham
A
Department of Organic Chemistry, CNT, NOVUM Research Park, SE-141 57 Huddinge, Sweden.
Latypov
Nikolaj V
NV
Wellmar
Ulf
U
Bemm
Ulf
U
Goede
Patrick
P
Bergman
Jan
J
Romero
Ivan
I
D018360:Crystallography, X-Ray; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D015394:Molecular Structure; D009566:Nitrates / Q000737:chemistry*; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000737:chemistry*; D013696:Temperature; D014508:Urea / Q000737:chemistry
D009566:Nitrates; D011743:Pyrimidines; D014508:Urea; C030986:pyrimidine