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Synthesis 2009(16): 2802-2808  
DOI: 10.1055/s-0029-1216874
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

The First Mineral-Catalyzed One-Pot [3+1+2] Coupling Protocol for Multifunctionalized Fused-Ring Pyrimidines

Lal Dhar S. Yadav*, Ankita Rai
Green Synthesis Lab, Department of Chemistry, University of Allahabad, Allahabad 211002, India
Fax: +91(532)2460533; e-Mail: ldsyadav@hotmail.com;
Further Information

Publication History

Received 14 April 2009
Publication Date:
26 June 2009 (online)

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Abstract

This is the first report on montmorillonite K-10 clay (nanoclay)-catalyzed, domino reactions of unprotected d-glucose/d-xylose with amidines/guanidine and an activated natural amino acid 2-phenyl-1,3-oxazol-5-one. The procedure results in an efficient annulation of the iminosugar moiety with functionalized pyrimidines­ in excellent yields (79-92%) with high trans-diaste­reoselectivity (>94%). The reaction is effected under solvent-free microwave irradiation conditions via amidine/guanidine-driven coupling and ring-transformation reactions in a one-pot procedure.

Key words

carbohydrates - mineral-catalyzed - amidines/guanidine - microwaves - ring transformation - pyrimidines

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