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
Further Information

Publication History

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

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.

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