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

研究成果: Article査読

9 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)411-414
ページ数4
ジャーナルTetrahedron Letters
55
2
DOI
出版ステータスPublished - 2014 1 8

ASJC Scopus subject areas

  • 生化学
  • 創薬
  • 有機化学

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