Regioselective synthesis of N-substituted dihydropyrimidin-2(1H) or (3H)-one

Hidetsura Cho, Yumi Takeuchi, Masaru Ueda, Akira Mizuno

Research output: Contribution to journalArticlepeer-review

18 Citations (Scopus)

Abstract

Alkoxycarbonylation of dihydropyrimidin-2-one 1 with alkyl chloroformate in the presence of NaH occurred regioselectively at position-3 to provide N-substituted dihydropyrimidin-2(1H)-one 2, but the reaction of 1 with trichloromethyl chloroformate (phosgene dimer) and aminoalcohol in the presence of NaH and Et3N afforded regioselectively N-substituted dihydropyrimidin-2(3H)-one 3 or compound 2. In this case, regioselectivity was dependent upon the substitution pattern of the phenyl ring. The reaction of 1 with phosgene dimer and ordinary alcohol in the base gave regioselectively compound 3 in contrast to the result of alkyl chloroformate method.

Original languageEnglish
Pages (from-to)5405-5408
Number of pages4
JournalTetrahedron Letters
Volume29
Issue number42
DOIs
Publication statusPublished - 1988

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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