Construction of dihydropyrimidine skeleton using 1,2,4-trisubstituted-1,3- diaza-1,3-butadienes

Hidetsura Cho, Yoshio Nishimura, Yoshizumi Yasui, Masahiko Yamaguchi

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

Construction of a dihydropyrimidine ring was developed that involved the cyclization of 1,3-diaza-1,3-butadienes having an N-protecting group (N-Cbz, N-Boc, N-alkyl, or N-benzyl) with α,β-unsaturated carbonyl compounds such as ethyl acrylate and p-chlorophenyl vinyl ketone. Consequently, 4-dimethylamino-2-phenyl-1,4,5,6-tetrahydropyrimidines were synthesized in good yields. Subsequently, the β-elimination of the dimethylamino group was carried out with MeI or SiO 2 to afford various N-protecting-2,5- disubstituted-1,6-dihydropyrimidines in good yields. Remarkably, the use of 4-chlorophenyl vinyl ketone directly provided the dihydropyrimidine without the tetrahydropyrimidine intermediate in excellent yield.

Original languageEnglish
Pages (from-to)1177-1179
Number of pages3
JournalTetrahedron Letters
Volume53
Issue number9
DOIs
Publication statusPublished - 2012 Feb 29

Keywords

  • Cyclization
  • Cycloaddition
  • Dienes
  • Dihydropyrimidine
  • Heterocycles

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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