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.

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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.

Item Type: Article
Subjects: Natural Product Chemistry
Depositing User: Dr. Aparna Maitra Pati
Date Deposited: 29 Dec 2011 16:04
Last Modified: 13 Feb 2012 04:58

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