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Synthesis 2009(11): 1786-1790  
DOI: 10.1055/s-0028-1088079
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

One-Pot Synthesis of 3-Acyl-2-(alkylsulfanyl)indoles and 2-(Alkylsulfanyl)indole-3-carboxylates from (2-Isocyanophenyl)methyl Ketones or (2-Isocyanophenyl)acetates

Shuhei Fukamachi, 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;
Further Information

Publication History

Received 16 December 2008
Publication Date:
27 April 2009 (online)

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Abstract

An efficient method has been developed for the preparation of 3-acyl-2-(alkylsulfanyl)indoles and ethyl 2-(alkylsulfanyl)indole-3-carboxylates under mild conditions. (2-Iso­-cyanophenyl)methyl ketones and ethyl 2-(2-isocyanophenyl)acetates were converted into the corresponding isothiocyanates by treatment with sulfur in the presence of a catalytic amount of selenium. The isothiocyanates were then treated with two equivalents of sodium hydride to form reactive disodium indol-1-ide-2-thiolate intermediates that were treated with alkyl halides to give the desired indole derivatives in a one-pot process. The method has been applied to the construction of three new indole-fused tricyclic structures by using α,ω-dibromoalkanes.

Key words

indoles - isocyanides - isothiocyanates - ring closure - sodium hydride

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