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An unusual, mild and convenient one-pot two-step access to (E)-stilbenes from hydroxy-substituted benzaldehydes and phenylacetic acids under microwave activation: a new facet of the classical Perkin reaction*

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Title An unusual, mild and convenient one-pot two-step access
to (E)-stilbenes from hydroxy-substituted benzaldehydes
and phenylacetic acids under microwave activation: a
new facet of the classical Perkin reaction*
 
Creator Sinha, Arun K
Kumar, Vinod
Sharma, A
Sharma, A
 
Subject Natural Product Chemistry
 
Description A mild and convenient one-pot two-step synthesis of hydroxystilbenes with trans selectivity has been developed through a modified
Perkin reaction between benzaldehydes and phenylacetic acids bearing 4- or 2-hydroxy substitution at the aromatic ring, in the presence
of piperidine–methylimidazole and polyethylene glycol under microwave irradiation. The observation of a simultaneous condensation–decarboxylation
leading to the unusual formation of hydroxystilbenes in lieu of a-phenylcinnamic acid reveals an interesting facet to the classical
Perkin reaction. The developed protocol provides a green alternative to the prevalent methods employing a toxic decarboxylating agent in
the form of quinoline/Cu salt, and the requirement for harsh protection–deprotection steps for the synthesis of hydroxylated stilbenes.
2007 Elsevier Ltd. All rights reserved.
 
Date 2007
 
Type Article
PeerReviewed
 
Format application/pdf
 
Identifier http://ihbt.csircentral.net/534/1/377_2007_2-12-2011_An_unusal.pdf
Sinha, Arun K and Kumar, Vinod and Sharma, A and Sharma, A (2007) An unusual, mild and convenient one-pot two-step access to (E)-stilbenes from hydroxy-substituted benzaldehydes and phenylacetic acids under microwave activation: a new facet of the classical Perkin reaction*. Tetrahedron, 63. pp. 11070-11077.
 
Relation http://ihbt.csircentral.net/534/