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Synthesis 2008(7): 1094-1098  
DOI: 10.1055/s-2008-1032120
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (Z)-2-[(Z)-3-Alkylideneisobenzofuran-1(3H)-ylidene]acetic Acid Derivatives by Sequential Coupling-Cyclization between 3-(2-Iodophenyl)-3-oxopropanoic Acid Derivatives and Terminal Alkynes

Kazuhiro Kobayashi*, Kenichi Hashimoto, Shuhei Fukamachi, Hisatoshi Konishi
Department of Materials Science, Faculty 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 14 November 2007
Publication Date:
06 March 2008 (online)

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Abstract

3-(2-Iodophenyl)-3-oxopropanoic acid derivatives reacted efficiently with various terminal alkynes in the presence of catalytic amounts of dichlorobis(triphenylphosphine)palladium and copper(I) iodide and two molar amounts of triethylamine in N,N-dimethylformamide at room temperature to afford the corresponding (Z)-2-[(Z)-3-alkylideneisobenzofuran-1(3H)-ylidene]acetic acid derivatives in reasonable yields.

Key words

alkynes - coupling - furans - palladium - ring closure