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

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

研究成果: Article

26 引用 (Scopus)

抄録

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.

元の言語English
ページ(範囲)1941-1949
ページ数9
ジャーナルBulletin of the Chemical Society of Japan
79
発行部数12
DOI
出版物ステータスPublished - 2006

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Quinolines
Iridium
Aldehydes
Aniline Compounds
Imines
Cyclization
Oxidants
Oxygen
Oxidation
Catalysts

ASJC Scopus subject areas

  • Chemistry(all)

これを引用

Facile three-component synthesis of substituted quinolines catalyzed by iridium(III) complex. / Nakajima, Takayuki; Inada, Takashi; Igarashi, Takeyuki; Sekioka, Tadashi; Shimizu, Isao.

:: Bulletin of the Chemical Society of Japan, 巻 79, 番号 12, 2006, p. 1941-1949.

研究成果: Article

Nakajima, Takayuki ; Inada, Takashi ; Igarashi, Takeyuki ; Sekioka, Tadashi ; Shimizu, Isao. / Facile three-component synthesis of substituted quinolines catalyzed by iridium(III) complex. :: Bulletin of the Chemical Society of Japan. 2006 ; 巻 79, 番号 12. pp. 1941-1949.
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