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Synthesis 2008(5): 719-724  
DOI: 10.1055/s-2008-1032175
PAPER
© Georg Thieme Verlag Stuttgart · New York

Indium(III) Chloride Catalyzed Addition of Indoles to Activated Aza-aromatic Systems

Jhillu S. Yadav*, Basi V. Subba Reddy, Puttagari Vishnumurthy, Kokku Premalatha
Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500 007, India
Fax: +91(40)27160512; e-Mail: yadavpub@iict.res.in;
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Publication History

Received 14 August 2007
Publication Date:
18 February 2008 (online)

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Abstract

Addition of indoles and pyrroles to activated quinolines and isoquinolines is achieved using 10 mol% of indium(III) chloride as a catalyst to produce 2-(1H-indol-3-yl)-1,2-dihydroquinolines and 1-(1H-indol-3-yl)-1,2-dihydroisoquinolines in excellent yields with high selectivity. This method is very useful for the functionalization of both indoles and quinolines in a one-pot operation.

Key words

aza-aromatics - indium reagents - indol-3-ylquinolines - pyrrol-2-ylquinolines