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Synthesis 2004(1): 106-110  
DOI: 10.1055/s-2003-44364
PAPER
© Georg Thieme Verlag Stuttgart · New York

InBr3-Catalyzed Conjugate Addition of Indoles to p-Quinones: An Efficient Synthesis of 3-Indolylquinones

J. S. Yadav*, B. V. S. Reddy, T. Swamy
Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad-500 007, India
Fax: +91(40)27160512; e-Mail: yadav@iict.ap.nic.in;
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Publication History

Received 31 July 2003
Publication Date:
09 December 2003 (online)

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Abstract

Indium(III) bromide catalyzes efficiently the conjugate addition of indoles to p-benzoquinones under mild conditions to afford the corresponding 3-indolylquinones in high yields with high selectivity. 1,4-Naphthoquinones also underwent Michael addition with indoles under similar conditions to give 3-indolylnaphthoquinones.

Key words

p-quinones - indoles - indium compounds - indol-3-ylbenzoquinones