Synlett 2012; 23(11): 1639-1642
DOI: 10.1055/s-0031-1291146
letter
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 4-Quinolones through Nickel-Catalyzed Intramolecular Amination on the β-Carbon of o-(N-Alkylamino)propiophenones

Satoshi Ueno*
Department of Chemistry, Graduate School of Sciences, Kyushu University, 6-10-1 Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan, Fax: +81(92)6422572   Email: ueno@chem.kyushu-univ.jp
,
Ryosuke Shimizu
Department of Chemistry, Graduate School of Sciences, Kyushu University, 6-10-1 Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan, Fax: +81(92)6422572   Email: ueno@chem.kyushu-univ.jp
,
Ryohei Maeda
Department of Chemistry, Graduate School of Sciences, Kyushu University, 6-10-1 Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan, Fax: +81(92)6422572   Email: ueno@chem.kyushu-univ.jp
,
Ryoichi Kuwano*
Department of Chemistry, Graduate School of Sciences, Kyushu University, 6-10-1 Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan, Fax: +81(92)6422572   Email: ueno@chem.kyushu-univ.jp
› Author Affiliations
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Publication History

Received: 09 March 2012

Accepted after revision: 08 April 2012

Publication Date:
13 June 2012 (online)


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Abstract

o-(N-Alkylamino)propiophenones are converted into 4-quinolones in the presence of chlorobenzene, potassium phosphate, morpholine, and nickel(0) catalyst. The reaction proceeds through the nickel-catalyzed formation of β-enaminones from o-(N-alkylamino)propiophenones and morpholine, followed by the intramolecular transamination.

Supporting Information