Addition of 4-Ethoxyimidazoles to Dimethyl Acetylenedicarboxylate and Transformation of the Adducts to Pyrimidin-5-yl Acetates1)

Syuichi Furuya, Kiyoshi Omura, Yoshiyasu Furukawa

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

Four new 4-ethoxy-2-substituted imidazoles (1) were synthesized and high reactivity toward electrophiles was observed at the 5-position rather than the N atoms. For example, 1 reacted with dimethyl acetylenedicarboxylate to afford dimethyl (4-ethoxyimidazol-5-yl)fumarates (6) and-maleates (5). When 6 was treated with acid, a novel ring transformation occurred to give methyl (6-ethoxycarbonyl-3,4-dihydro-4-oxopyrimidin-5-yl)acetates (12).

Original languageEnglish
Pages (from-to)1669-1675
Number of pages7
JournalChemical and Pharmaceutical Bulletin
Volume36
Issue number5
DOIs
Publication statusPublished - 1988

Keywords

  • 4-ethoxyimidazole
  • addition
  • benzylation
  • dimethyl acetylenedicarboxylate
  • pyrimidin-5-yl acetate
  • ring transformation
  • synthesis

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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