TY - JOUR
T1 - Facile three-component synthesis of substituted quinolines catalyzed by iridium(III) complex
AU - Nakajima, Takayuki
AU - Inada, Takashi
AU - Igarashi, Takeyuki
AU - Sekioka, Tadashi
AU - Shimizu, Isao
PY - 2006
Y1 - 2006
N2 - 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.
AB - 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.
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U2 - 10.1246/bcsj.79.1941
DO - 10.1246/bcsj.79.1941
M3 - Article
AN - SCOPUS:33845574410
SN - 0009-2673
VL - 79
SP - 1941
EP - 1949
JO - Bulletin of the Chemical Society of Japan
JF - Bulletin of the Chemical Society of Japan
IS - 12
ER -