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Issue 5, 2011
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Heteropoly acid-catalyzed microwave-assisted three-component aza-Diels–Alder cyclizations: diastereoselective synthesis of potential drug candidates for Alzheimer's disease

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Abstract

A highly diastereoselective microwave-assisted three component synthesis of azabicyclo[2.2.2]octan-5-ones by a silicotungstic acid-catalyzed aza-Diels–Alder cyclization is described. The one-pot process involves the formation of the in situ generated Schiff base and its immediate cyclization with cyclohex-2-enone. The short reaction times, good yields and excellent diastereoselectivity make this annulation a practical and environmentally attractive method for the synthesis of the target compounds. Preliminary assays were carried out to determine the activity of the products in AChE as well as in amyloid β fibrillogenesis inhibition.

Graphical abstract: Heteropoly acid-catalyzed microwave-assisted three-component aza-Diels–Alder cyclizations: diastereoselective synthesis of potential drug candidates for Alzheimer's disease

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Article information


Submitted
28 Aug 2010
Accepted
05 Nov 2010
First published
09 Nov 2010

Org. Biomol. Chem., 2011,9, 1394-1401
Article type
Paper

Heteropoly acid-catalyzed microwave-assisted three-component aza-Diels–Alder cyclizations: diastereoselective synthesis of potential drug candidates for Alzheimer's disease

D. Borkin, E. Morzhina, S. Datta, A. Rudnitskaya, A. Sood, M. Török and B. Török, Org. Biomol. Chem., 2011, 9, 1394
DOI: 10.1039/C0OB00638F

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