Convergent synthesis of 2-aryl-substituted quinolines by gold-catalyzed cascade reaction

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Abstract

Gold-catalyzed auto-tandem catalysis has been developed for synthesizing 2-aryl-substituted quinolines. The reaction of an aniline bearing an acetal moiety with an aryl alkyne proceeded via formal [4+2]-cycloaddition, which involved the addition of gold acetylide to an oxonium ion to give amino alkyne intermediate and sequential 6-endo-dig cyclization of amino alkyne intermediate by attacking of nitrogen to alkyne moiety activated by gold catalyst. The cationic gold catalyst promoted two different processes by enhancing the nucleophilicity and electrophilicity of alkyne. This convergent synthetic methodology enabled the synthesis of a variety of 2-aryl-substituted quinolines.

Original languageEnglish
Pages (from-to)824-829
Number of pages6
JournalChemical and Pharmaceutical Bulletin
Volume64
Issue number7
DOIs
Publication statusPublished - 2016

Keywords

  • Cyclization
  • Gold catalysis
  • Heterocyclic compound
  • Quinoline
  • Tandem reaction

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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