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Synthesis 2009(20): 3378-3382  
DOI: 10.1055/s-0029-1216949
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

One-Pot Synthesis of Quinoline-2(1H)-thiones from 2-Isocyanostyrenes via Electrocyclic Reaction of the Corresponding 2-Isothiocyanatestyrenes

Kazuhiro Kobayashi*, Seiki Fujita, Shuhei Fukamachi, Hisatoshi Konishi
Division of Applied Chemistry, Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan
Fax: +81(857)315263; e-Mail: kkoba@chem.tottori-u.ac.jp;
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Publication History

Received 8 May 2009
Publication Date:
21 August 2009 (online)

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Abstract

The reaction of α-substituted 2-isocyanostyrenes, which could be readily prepared from commercially available 2-aminophenyl ketones or 2-aminobenzonitriles, with sulfur in the presence of a catalytic amount of selenium proceeded smoothly to give the corresponding 2-isothiocyanatestyrenes. The latter spontaneously underwent the electrocyclic reaction to afford 4-substituted quinoline-2(1H)-thiones in one-pot with isolated yields ranging from 37 to 91%.

Key words

quinoline-2(1H)-thiones - isocyanides - electrocyclic reaction - isothiocyanates - sulfur