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Synthesis 2011(1): 168-172  
DOI: 10.1055/s-0030-1258336
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Indium(III) Chloride Catalyzed, Novel and Efficient Synthesis of Sugar-Annulated N-Aryltetrahydropyridines

B. V. Subba Reddy*a, Ch. Divya Vania,c, Zubeda Beguma, J. S. Yadava, T. Prabhakar Raob
a Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500 007, India
Fax: +91(40)27160512; e-Mail: yadavpub@iict.res.in;
b Centre for Nuclear Magnetic Resonance, Indian Institute of Chemical Technology, Hyderabad 500 007, India
c IICT an Associate Institution of University of Hyderabad, Hyderabad 500 007, India
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Publication History

Received 6 September 2010
Publication Date:
26 November 2010 (online)

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Abstract

δ-Hydroxy-α,β-unsaturated aldehydes undergo smooth coupling with enamines derived from arylamines and 1,3-diketones in the presence of 10% InCl3 in CH2Cl2 under mild reaction conditions to afford sugar fused N-aryltetrahydropyridine derivatives in good yields with high selectivity. The salient features of this method are high conversions, mild reaction conditions, short reaction times, high selectivity and operational simplicity.

Key words

Perlin aldehyde - 1,3-diketones - indium(III) salts - N-aryltetrahydropyridines