Synthesis of 4-unsubstituted dihydropyrimidines. Nucleophilic substitution at position-2 of dihydropyrimidines

Hidetsura Cho, Yoshio Nishimura, Yoshizumi Yasui, Satoshi Kobayashi, Shin Ichiro Yoshida, Eunsang Kwona, Masahiko Yamaguchi

研究成果: Article査読

27 被引用数 (Scopus)

抄録

Synthesis of novel 4-unsubstituted dihydropyrimidines (DPs) was performed. Subsequently, a variety of 4-unsubstituted 1,4(3,4)-DPs with amino moieties at position-2 were obtained in excellent yields by activation of position-2 owing to regioselective alkoxycarbonylation at position-3 of the DP skeleton. 3-Oxo-2-phenyl-2,3,5,8-tetrahydro[1,2,4]triazolo[4,3-a]pyrimidine was obtained using phenylhydrazine instead of amines. Individual tautomers of 1,4(3,4)-DP were observed in the 1H NMR spectra of one derivative depending on temperature and concentration. On the other hand, only 1,4-DP was found in the solid state by single-crystal X-ray crystallography.

本文言語English
ページ(範囲)2661-2669
ページ数9
ジャーナルTetrahedron
67
14
DOI
出版ステータスPublished - 2011 4月 8
外部発表はい

ASJC Scopus subject areas

  • 生化学
  • 創薬
  • 有機化学

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