Synthesis of methyl 3-(N'-alkylureido)-2-methyl-2-propenoates and their cyclization to 3-alkyl-5-methyluracils
- 1 January 1982
- journal article
- Published by Institute of Organic Chemistry & Biochemistry in Collection of Czechoslovak Chemical Communications
- Vol. 47 (2) , 676-688
- https://doi.org/10.1135/cccc19820676
Abstract
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-butyl-thiourea 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.Keywords
This publication has 0 references indexed in Scilit: