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Synthesis 2010(10): 1719-1723  
DOI: 10.1055/s-0029-1218721
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Three-Component Reaction of a δ-Hydroxy-α,β-Unsaturated Aldehyde with Arylamines and 1,3-Diketones: A Novel Synthesis of Oxa-Aza Bicycles

Basi V. Subba Reddy*a, Ch. Divyavania,b, Zubeda Beguma, Jhillu S. Yadava
a Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500007, India
Fax: +91(40)27160512; e-Mail: basireddy@iict.res.in;
b IICT - An Associate Institution of the University of Hyderabad, Hyderabad 500007, India
Further Information

Publication History

Received 8 February 2010
Publication Date:
06 April 2010 (online)

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Abstract

δ-Hydroxy-α,β-unsaturated sugar aldehydes (Perlin aldehydes) undergo smooth coupling with β-enamino ketones and β-enamino esters generated in situ from arylamines and 1,3-dicarbonyl compounds in the presence of 10 mol% InCl3 in acetonitrile at 80 ˚C, to produce oxa-aza-bicycles in good yields with high selectivity.

Key words

Perlin aldehyde - 1,3-dicarbonyl compounds - indium salts - oxa-aza-bicycles

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