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Paper | Regular issue | Vol 81, No. 4, 2010, pp.935-942
Published online, 9th February, 2010
DOI: 10.3987/COM-09-11890
A Highly Effective One-Pot Synthesis of Quinolines from 2-Alkynylnitrobenzenes

Kentaro Okuma,* Saori Ozaki, Jun-ichi Seto, Noriyoshi Nagahora, and Kosei Shioji

*Department of Chemistry, Faculty of Sciences, Fukuoka University, 8-19-1 Nanakuma, Jonan-ku, Fukuoka 814-0180, Japan

Abstract

A highly effective one-pot synthesis of poly-substituted quinolines from 2-alkynylnitrobenzenes using inexpensive reagents has been developed. Reaction of 2-alkynylnitrobenzenes with Sn/HCl in EtOH resulted in the formation of 2-aminophenyl ketones and subsequently condensed in situ with ketones to form tri-substituted quinolines in 80-97% yields.