Facile three-component synthesis of substituted quinolines catalyzed by iridium(III) complex

Takayuki Nakajima, Takashi Inada, Takeyuki Igarashi, Tadashi Sekioka, Isao Shimizu

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

A convenient and efficient synthesis of substituted quinolines via a simple one-pot reaction of an aniline, an aromatic aldehyde, and an enolizable aliphatic aldehyde in the presence of the iridium catalyst [IrCl 2H(cod)]2 under oxygen as an oxidant was developed. The reaction proceeds with Mannich-type imine formation followed by nucleophilic addition to give β-amino aldehydes. Dehydrative cyclization takes place to give dihydroquinoline, which is then dehydrogenated by aerobic oxidation to give 2-aryl-3-alkylquinolines. Dialkylquinolines were obtained by the reaction with anilines and aliphatic aldehydes in good yields.

Original languageEnglish
Pages (from-to)1941-1949
Number of pages9
JournalBulletin of the Chemical Society of Japan
Volume79
Issue number12
DOIs
Publication statusPublished - 2006

ASJC Scopus subject areas

  • Chemistry(all)

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