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

Dmitry Borkin; Elena Morzhina; Silpi Datta; Aleksandra Rudnitskaya; Abha Sood; Marianna Török; Béla Török

doi:10.1039/c0ob00638f

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

Dmitry Borkin
, Elena Morzhina
, Silpi Datta
, Aleksandra Rudnitskaya
, Abha Sood
, Marianna Török
, Béla Török

Chemistry

University of Massachusetts Boston

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	1394-1401
Number of pages	8
Journal	Organic and Biomolecular Chemistry
Volume	9
Issue number	5
DOIs	https://doi.org/10.1039/c0ob00638f
State	Published - Mar 1 2011

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1039/c0ob00638f

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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. / Borkin, Dmitry; Morzhina, Elena; Datta, Silpi et al.
In: Organic and Biomolecular Chemistry, Vol. 9, No. 5, 01.03.2011, p. 1394-1401.

Research output: Contribution to journal › Article › peer-review

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AU - Török, Marianna

AU - Török, Béla

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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

Abstract

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