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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*

IR@IHBT: CSIR-Institute of Himalayan Bioresource Technology, Palampur


Field	Value

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%2D12%2D2011_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/