tert-Butoxide-Mediated Synthesis of 3,4′-Biquinolines from 2-Aminochalcones

Jiye Jeon, So Young Lee, Cheol-Hong Cheon

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

A novel protocol to synthesize 3,4’-biquinolines from 2-aminochalcones in the presence of a stoichiometric amount of sodium tert-butoxide as the nucleophilic promotor was developed. Conjugate addition of tert-butoxide to 2-aminochalcones provided the corresponding enolates, which underwent Michael addition to another molecule of 2-aminochalcone to afford a dimeric species of 2-aminochalcones. Subsequent cyclization between the amino and carbonyl groups followed by aromatization provides 3,4’-biquinoline products. Various 2-aminochalcones were submitted to this protocol and the desired 3,4’-biquinoline products were obtained in good to high yields in a short reaction time.

Original languageEnglish
JournalAdvanced Synthesis and Catalysis
DOIs
Publication statusPublished - 2019 Jan 1

Keywords

  • 2-Aminochalcones
  • Biquinolines
  • Dimerization
  • Nucleophilic Catalyst
  • tert-Butoxide

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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