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

Yoshio Nishimura, Yoshizumi Yasui, Satoshi Kobayashi, Masahiko Yamaguchi, Hidetsura Cho

Research output: Contribution to journalArticlepeer-review

14 Citations (Scopus)

Abstract

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-C 4H 9, N-Bn or N-Ph) with electron-deficient olefins, such as α,β-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 β-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.

Original languageEnglish
Pages (from-to)3342-3350
Number of pages9
JournalTetrahedron
Volume68
Issue number16
DOIs
Publication statusPublished - 2012 Apr 22
Externally publishedYes

Keywords

  • 1,3-Diaza-1,3-butadiene
  • 2,5-Disubstituted dihydropyrimidine
  • Cyclization
  • Tautomerism
  • Tetrahydropyrimidine

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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