Synthesis of 3-substituted 3,4-dihydropyrimidines: N-Alkoxycarbonylation with trichloromethyl chloroformate and alcohols

Hidetsura Cho, Akira Mizuno, Keiyuu Shima, Masaru Ueda, Yumi Takeuchi, Mikiko Hamaguchi, Nobuaki Taniguchi

Research output: Contribution to journalArticlepeer-review

8 Citations (Scopus)

Abstract

N-Alkoxycarbonylation reactions of dihydropyrimidines with trichloromethyl chloroformate (phosgene dimer) and an alcohol were carried out in order to obtain the dihydropyrimidines with a complicated alkyl group or an alkyl group containing a nitrogen atom. Especially, the synthetically difficult problem of the unstable N-substituted dihydropyrimidines containing a nitrogen atom in an ester group was overcome by the method II: 0.5-1.2 mol equiv. of phosgene dimer, 1.0-6.0 equiv. of tertiary aminoalcohol, and 6 equiv. of Et3N in THF at -23 °C-r.t.

Original languageEnglish
Pages (from-to)769-774
Number of pages6
JournalHeterocycles
Volume27
Issue number3
DOIs
Publication statusPublished - 1988 Mar 1

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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