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Synthesis 2005(16): 2673-2676  
DOI: 10.1055/s-2005-872086
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Convenient Synthesis of 3-(1-Aminoalkyl)quinolin-2(1 H )-one Derivatives

Kazuhiro Kobayashi*, Yuhei Fuchimoto, Kazutaka Hayashi, Masaaki Mano, Miyuki Tanmatsu, Osamu Morikawa, Hisatoshi Konishi
Department of Materials Science, Faculty of Engineering, Tottori University, Koyama-minami, Tottori 680-8552, Japan
Fax: +81(857)315263; e-Mail: kkoba@chem.tottori-u.ac.jp;
Further Information

Publication History

Received 29 March 2005
Publication Date:
20 July 2005 (online)

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Abstract

Treatment of magnesium enolates of 1-methyl-3,4-dihydroquinolin-2(1H)-ones with nitriles, followed by N-acetylation of the resulting vinylogous urea derivatives with acetic anhydride/pyridine and double bond migration with 1,8-diazabicyclo[5.3.0]undec-7-ene, affords 3-[1-(acetylamino)alkyl]-1-methylquinolin-2(1H)-one derivatives in reasonable overall yields.

Key words

carbanion - lactams - magnesium - nitriles - quinolines

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