Synthesis of 1,6-dihydropyrimidines via copper-catalyzed multistep cascade reactions between O-propargylic aldoximes and isocyanates

Itaru Nakamura, Toshiki Onuma, Dong Zhang, Masahiro Terada

Research output: Contribution to journalArticlepeer-review

16 Citations (Scopus)

Abstract

Multi-step cascade reactions of O-propargylic oximes with isocyanates were carried out in the presence of copper catalysts to afford the corresponding 1,6-dihydropyrimidines in good yields. The multi-step reactions consisted of a 2,3-rearrangement, a [3+2] cycloaddition, decarboxylative ring opening involving a 1,4-hydrogen shift, and a 6π-electrocyclization.

Original languageEnglish
Pages (from-to)1178-1182
Number of pages5
JournalTetrahedron Letters
Volume55
Issue number6
DOIs
Publication statusPublished - 2014 Feb 5

Keywords

  • Alkyne
  • Cascade reaction
  • Copper-catalyzed
  • Oximes
  • Rearrangement

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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