%0 Journal Article
%T Synthesis of 2-substituted 6-(5-oxo-1-phenylpyrrolidin-3-yl)pyrimidin-4(3H)-ones
%A Uros Groselj
%A Georg Dahmann
%A Branko Stanovnik
%A Jurij Svete
%J European Journal of Chemistry
%D 2013
%I 
%R 10.5155/eurjchem.4.1.1-6.718
%X 2-Substituted 6-(5-oxo-1-phenylpyrrolidin-3-yl)pyrimidin-4(3H)-ones were synthesized in three steps from itaconic acid derivatives via cyclization with primary amines followed by Masamune-Claisen condensation, and cyclization of the newly formed ¦Â-keto esters with amidines. Preparation and/or isolation of ¦Â-keto esters with polar N-substituents failed, but the corresponding final products were obtained in a different way. 6-(1-(3-Hydroxypropyl)-5-oxopyrrolidin-3-yl)-2-phenylpyrimidin-4(3H)-one was obtained by hydrogenolytic o-deprotection of its o-benzyl derivative. Depending on reaction conditions, further mesylation of 6-(1-(3-(benzyloxy)propyl)-5-oxopyrrolidin-3-yl)-2-phenylpyrimidin-4(3H)-one followed by treatment with pyrrolidine gave either the monoaminated- or the diaminated product. The structures of novel compounds were determined by NMR.
%K Lactams
%K Cyclization
%K Heterocycles
%K Medicinal chemistry
%K Nitrogen heterocycles
%K Nucleophilic substitution
%U http://www.eurjchem.com/index.php/eurjchem/article/view/718