29458-39-7Relevant academic research and scientific papers
SOLVATION EFFECTS IN THE METHYLATION OF BARBITURIC ACID AND ITS DERIVATIVES BY DIAZOMETHANE
Krasnov, K. A.,Slesarev, V. I.,Zakharov, A.P.,Grigor'eva, E. G.
, p. 1218 - 1221 (1987)
Methylation of barbituric acid and its N-methylderivatives by diazomethane in ethers and methanol occurs only at the oxygen atom of the β-dicarbonyl fragment.The resulting 6-methoxy-2,4-dioxo-1,2,3,4-tetrahydropyrimidine and its derivatives are methylated at both the oxygen and nitrogen atoms; relative to ethers, methanol facilitates a greater degree of methylation at the nitrogen atom.
ALKYLATION OF BARBITURIC ACIDS BY ALCOHOLS AS A METHOD FOR THE SYNTHESIS OF 6-ALKOXYURACILS
Rudenko, E. S.,Krasnov, K. A.,Slesarev, V. I.
, p. 2337 - 2341 (2007/10/02)
The alkylation of barbituric acid, 2-thiobarbituric acid, and their N-methyl derivatives by aliphatic alcohols in the presence of acidic catalysts gives high yields of 6-alkoxyuracils.In the case of methanol and 2-methyl-1-propanol the best catalyst is boron trifluoride etherate. 2-Thiobarbituric acids are alkylated more easily than the corresponding barbituric acids.
REACTION OF BARBITURIC ACID AND ITS METHYL DERIVATIVES WITH DIAZOMETHAN IN ETHERS
Krasnov, K. A.,Slesareva, V. I.,Studentsov, E. P.,Slesarev, V. I.
, p. 1765 - 1769 (2007/10/02)
A full scheme for the methylation of barbituric acid with diazomethane in diethyl ether, glyme, and THF was formulated.For barbituric acid and its N-methyl derivatives the reaction takes place at the oxygen atoms of the β-dicarbonyl fragment.The 6-methoxyuracil and its derivatives which are formed here are subsequently methylated at the nitrogen and oxygen atoms.The reaction takes place in accordance with the structures of the monoanions of the compounds being methylated.
