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Synthesis 2010(4): 666-670  
DOI: 10.1055/s-0029-1218609
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of 2,3-Bis(arylamino)benzofurans and 2,3-Bis(arylimino)-2,3-dihydrobenzofurans by a Lewis Acid Catalyzed Reaction of 2-Aryliminophenols with Aryl Isocyanides

Kazuhiro Kobayashi*, Yuu Shirai, 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 6 October 2009
Publication Date:
16 December 2009 (online)

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Abstract

An efficient method for the preparation of 2,3-bis(aryl­amino)benzofurans and 2,3-bis(arylimino)-2,3-dihydrobenzofurans is described that is based on the reaction of 2-aryliminophenols with aryl isocyanides in the presence of a catalytic amount of boron tri­fluoride diethyl etherate. The reaction gives 2,3-bis(arylamino)benzofurans, some of which are transformed into 2,3-bis(arylimino)-2,3-dihydrobenzofurans by air oxidation, mostly during workup.

Key words

benzofurans - o-hydroxybenzylideneamines - isocyanides - boron trifluoride - imidoyl cations

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