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Synlett 2006(16): 2676-2678  
DOI: 10.1055/s-2006-949381
LETTER
© Georg Thieme Verlag Stuttgart · New York

Polyvinyl Pyridine as a Novel Solid Heterogeneous, Recyclable Catalyst for aza-Michael Reaction

Vivek P. Raje, Ramakrishna P. Bhat, Shriniwas D. Samant*
Organic Chemistry Research Laboratory, Department of Chemistry, Institute of Chemical Technology, University of Mumbai, N. M. Parekh Marg, Matunga, Mumbai-400 019, India
Fax: +91(22)24145614; e-Mail: samantsd@yahoo.com;
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Publication History

Received 15 January 2006
Publication Date:
22 September 2006 (online)

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Abstract

Polyvinyl pyridine (PVP) is prepared by radical polymerization of 4-vinyl pyridine. PVP was used as a heterogeneous basic catalyst for the aza-Michael reaction of secondary amines and carbamates with α,β-unsaturated esters, cyanides and ketones to ­obtain the corresponding adducts in excellent yields (70-90%).

Key words

polyvinyl pyridine - aza-Michael reaction - hetero­geneous solid base

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General Reaction Procedure.To the amine or carbamate (5 mmol) and Michael acceptor (5.5 mmol) was added PVP (5% by weight on the basis of amine/carbamate). The reaction mixture was stirred at r.t. until complete conversion of the starting material. The reaction mixture was filtered and the catalyst washed with Et2O. The crude product was purified by column chromatography. All products were characterized by 1H NMR and IR spectroscopy.