78681-07-9Relevant academic research and scientific papers
N-Acylation of 1,3-Dimethyl-6-aminouracils. A Reversal in the Regiospecificity of an Electrophilic Substitution Induced by an Intramolecular Proton-transfer
Bernier, Jean-Luc,Henichart, Jean-Pierre,Warin, Vincent
, p. 1129 - 1134 (2007/10/02)
Electrophilic reactions of 1,3-dimethyl-6-aminouracil lead to 5-substituted derivatives.The introduction of a dialkylaminoalkylamino chain in the 6-position of 1,3-dimethyluracil modifies the regiospecificity of the acylation reaction to give N-6 acylated compounds.This reversal in acylation is induced by an intramolecular proton-transfer which introduces a change in the electron density of the enamine system.The cyclic transition state and the spatial conformation of the final products substantiate the proposed mechanism, on the basis of X-ray and 1H nmr data.
REGIOSPECIFICITE DE L'ACYLATION DU DIMETHYL-1,3 MORPHOLINOETHYLAMINO-6 URACILE
Bernier, J. L.,Henichart, J. P.
, p. 1243 - 1246 (2007/10/02)
The regioselective reactivity of electrophilic agents toward 1,3-dimethyl amino-6 uracile derivatives has been well established but with a substitution of the extracyclic nitrogen atom by a morholinoethyl group a reversal of the regiospecificity may occur.
