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Synthesis 2010(15): 2571-2576  
DOI: 10.1055/s-0029-1218824
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Three-Component One-Pot Synthesis of 3-(2-Furanyl)indoles from Acetylenedicarboxylate, Isocyanide, and 3-Formylindole

B. V. Subba Reddy*a, A. Mallikarjun Reddya, D. Somashekara, J. S. Yadava, B. Sridharb
a Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500 007, India
b Centre for X-ray Crystallography, Indian Institute of Chemical Technology, Hyderabad 500 007, India
e-Mail: basireddy@iict.res.in;
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Publication History

Received 29 March 2010
Publication Date:
18 June 2010 (online)

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Abstract

The zwitterions derived from isocyanide and dimethyl acetylenedicarboxylate undergo smooth condensation with 3-formylindoles in benzene at room temperature to give the corresponding 3-(2-furanyl)indoles in good yields. This method provides a simple and convenient route to produce a wide range of 3-heteroarylindoles in a one-pot operation.

Key words

3-formylindoles - isocyanides - DMAD - zwitterions - 3-furanylindoles

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