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Synthesis 2010(17): 2985-2989  
DOI: 10.1055/s-0030-1258177
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of 3-Substituted 1-Thioacyl- and 1-Thiocarbamoylindoles from α-Substituted 2-Isocyanato-β-methoxystyrenes

Shuhei Fukamachi, Seiki Fujita, Kazuya Murahashi, Hisatoshi Konishi, Kazuhiro Kobayashi*
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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Publikationsverlauf

Received 19 March 2010
Publikationsdatum:
12. Juli 2010 (online)

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Abstract

3-Aryl-1-thioacylindoles were prepared by treating α-aryl-2-isothiocyanato-β-methoxystyrenes with organolithiums or Grignard reagents, followed by hydriodic acid catalyzed cyclization of the resulting adducts. A one-pot synthesis of 1-thiocarbamoylindoles was achieved by hydriodic acid mediated cyclization of the corresponding thiourea intermediates, prepared from α-substituted 2-isothiocyanato-β-methoxystyrenes and secondary amines.

Key words

heterocycles - indoles - cyclizations - isothiocyanates - organometallic reagents

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