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

Takayuki Nakajima, Takashi Inada, Isao Shimizu

Research output: Contribution to journalArticle

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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Quinolines
Iridium
Acetaldehyde
Methylation
Quinolones
Aldehydes
Potassium
Oxidation
quinoline
eduline
aniline
1,1-dimethoxyethane
graveoline

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Short step synthesis of natural 2-arylquinolones based on iridium-catalyzed three-component coupling quinoline synthesis. / Nakajima, Takayuki; Inada, Takashi; Shimizu, Isao.

In: Heterocycles, Vol. 69, No. 1, 01.12.2006, p. 497-504.

Research output: Contribution to journalArticle

Nakajima, Takayuki ; Inada, Takashi ; Shimizu, Isao. / Short step synthesis of natural 2-arylquinolones based on iridium-catalyzed three-component coupling quinoline synthesis. In: Heterocycles. 2006 ; Vol. 69, No. 1. pp. 497-504.
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