Synthesis of novel 2-phenyl-5-substituted dihydropyrimidines using 2-phenyl-1,3-diaza-1,3-butadienes and electron-deficient olefins

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• 作者：Yoshio Nishimura^a ; Yoshizumi Yasui^b ; Satoshi Kobayashi^c ; Masahiko Yamaguchi^b ; ^c ; Hidetsura Cho^c ; ^d ; ^{hcho@mail.pharm.tohoku.ac.jp}
• 关键词：2 ; 5-Disubstituted dihydropyrimidine ; 1 ; 3-Diaza-1 ; 3-butadiene ; Tetrahydropyrimidine ; Tautomerism ; Cyclization
• 刊名：Tetrahedron
• 出版年：2012
• 期刊代码：107_00404020
• 类别：ch
• 出版时间：22 April, 2012
• 卷：68
• 期：16
• 页码：3342-3350
• 文件大小：790 K

摘要

A novel synthetic method for 2,5-disubstituted dihydropyrimidines was developed. The cyclization of 1,3-diaza-4-dimethylamino-1,3-butadienes having a N-protecting group (N-Boc, N-Cbz, N-n-C₄H₉, N-Bn or N-Ph) with electron-deficient olefins, such as 伪,尾-unsaturated carbonyl compounds, phenyl vinyl sulfone, and acrylonitrile was studied in detail. The cyclization smoothly proceeded to afford 4-dimethylamino-1,4,5,6-tetrahydropyrimidines or 1,6-dihydropyrimidines in good yields. The isolated 4-dimethylamino-1,4,5,6-tetrahydropyrimidines were converted to 2,5-disubstituted-1,6-dihydropyrimidines through the 尾-elimination of the dimethylamino group. 2,5-Disubstituted-1,4(6)-dihydropyrimidines were obtained after removal of the N-Boc or N-Cbz group. Independent tautomers of the resulting dihydropyrimidines were observed.