Synthesis of 4-unsubstituted dihydropyrimidines having acyl and alkoxycarbonyl groups at 5- and 6-positions by cyclization-elimination reactions using 1,3-diaza-1,3-butadienes

Yoshio Nishimura, Hidetsura Cho

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9 Citations (Scopus)

Abstract

A synthetic method for novel 4-unsubstituted 2-phenyldihydropyrimidines having acyl and alkoxycarbonyl groups at the 5- and 6-positions was developed. The cyclization of 4-dimethylamino-1,3-diaza-1,3-butadiene having N-protecting groups (Boc, Cbz) with 1,2-disubstituted ethylenes, such as diethyl maleate, diethyl fumarate, (Z)-hex-3-ene-2,5-dione, (E)-1,4-diphenylbut-2-ene-1,4-dione, and unsymmetrical (E)-ethyl 4-oxo-4-phenylbut-2-enoate, following the elimination of a dimethylamino group proceeded smoothly, producing the corresponding dihydropyrimidines in good overall yield. The N-protecting group (Boc) could be easily removed to obtain N-unsubstituted dihydropyrimidines as a mixture of tautomers, and their tautomeric behavior was analyzed by 1H NMR spectroscopy.

Original languageEnglish
Pages (from-to)411-414
Number of pages4
JournalTetrahedron Letters
Volume55
Issue number2
DOIs
Publication statusPublished - 2014 Jan 8

Keywords

  • 1,2-Disubstituted ethylene
  • 1,3-Diaza-1,3-butadiene
  • 4-Unsubstituted dihydropyrimidine
  • Cyclization
  • Elimination

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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