The cyclization reaction of ortho-ethynylbenzaldehyde derivatives into isoquinoline derivatives

Takao Sakamoto, Atsushi Numata, Yoshinori Kondo

Research output: Contribution to journalArticlepeer-review

23 Citations (Scopus)

Abstract

In order to elucidate the reaction mechanism of the cyclization between an ethynyl group and an imino group at the ortho-position on an aromatic ring to afford isoquinolines, reaction of 2-ethynylbenzaldehydes under various conditions was examined. It is concluded that reaction proceeds via an ionic process and the isoquinoline 4-hydrogen atom derives from the solvent. In addition, it was found that 2-ethynylbenzaldehyde O-methyloximes underwent cyclization in the presence of primary and secondary alcohols to give 3- substituted isoquinolines.

Original languageEnglish
Pages (from-to)669-672
Number of pages4
JournalChemical and Pharmaceutical Bulletin
Volume48
Issue number5
DOIs
Publication statusPublished - 2000 May

Keywords

  • 2-ethynylbenzaldehyde
  • Cyclization
  • Isoquinoline
  • N-oxide
  • Palladium- catalyzed reaction

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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