82387-33-5Relevant academic research and scientific papers
SYNTHESIS OF METHYL 3-(N'-ALKYLUREIDO)-2-METHYL-2-PROPENOATES AND THEIR CYCLIZATION TO 3-ALKYL-5-METHYLURACILS
Ledvina, Miroslav,Farkas, Jiri
, p. 676 - 688 (2007/10/02)
Stereoisomeric methyl 3-(N'-alkylureido)-2-methyl-2-propenoates (Ia-Id) were prepared by acid-catalyzed reaction of N-alkylureas (R = methyl, benzyl, isopropyl and tert-butyl) with methyl 3-methoxy-2-methyl-2-propenoate (III).Reaction of the ester III with N-tert-butylthiourea afforded the thioureides (E)-Ie and (Z)-Ie.On treatment with sodium methoxide in methanol, compounds Ia-Ic cyclized to the corresponding 3-alkyl-5-methyluracils IIa-IIc whereas compounds Id and Ie underwent only a base catalyzed E/Z isomerization with (E)-isomers predominating.
