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Communication | Regular issue | Vol 22, No. 9, 1984, pp.1959-1963
Published online, 1st January, 1970
DOI: 10.3987/R-1984-09-1959
Synthesis of Novel 5-Alkoxycarbonyl-5,6-dihydropyrimidin-4(3H)-ones from 3-Substituted 2-Alkoxycarbonyl-2-propenoates and Amidines

Hidetsura Cho,* Masaru Ueda, Yoshiko Ohnaka, and Mariko Hayashimatsu

*Suntory Institute for Biochemical Research, Suntory Co. Ltd., 1-1-1, Wakayamadai, Shimamotocho, Mishimagun, Osaka 618-0024, Japan

Abstract

A cyclization of 3-substituted 2-alkoxycarbonyl-2-propenoates with acetamidine, benzamidine, guanidine, or 1,1-dimethylguanidine hydrochloride in the presence of 1-2 eq of metal alkoxide afforded novel 5-alkoxycarbonyl-5,6-dihydropyrimidin-4(3H)-ones in good yield (R1=Me, Et, iPr; R2=phenyl, furyl, thienyl, pyridyl, alkyl; R3=Me, C6H5, NH2, NMe2). Substitution of a functional group on the phenyl ring influenced the trans-cis relationship between the 5-proton and the 6-proton of the dihydropyrimidone skeleton, namely the ratio of trans/cis increased from ortho substitution (3/2-2/1) and meta (9/1) to para (only trans).