Short step synthesis of natural 2-arylquinolones based on iridium-catalyzed three-component coupling quinoline synthesis

Takayuki Nakajima, Takashi Inada, Isao Shimizu

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10 Citations (Scopus)

Abstract

Eduline (la), graveoline (1b), and 6-methoxy-2-(4-methoxyphenyl)-1-methylquinolone (1c) were synthesized by iridium-catalyzed three-component coupling reaction. Reaction of an aniline, an aromatic aldehyde, and acetaldehyde gave the corresponding substituted quinoline. Using 1,1-dimethoxyethane instead of acetaldehyde, the three component coupling reactions were also carried out to give the quinolines in higher yields. N-Methylation of the quinolines with methyl trifrate followed by oxidation with potassium ferricianate gave the quinolones.

Original languageEnglish
Pages (from-to)497-504
Number of pages8
JournalHeterocycles
Volume69
Issue number1
Publication statusPublished - 2006 Dec 1

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ASJC Scopus subject areas

  • Organic Chemistry

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