Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 9, Issue 5, Pages 1394-1401Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c0ob00638f
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Funding
- University of Massachusetts Boston
- National Institute of Health [R-15 AG025777-03]
- NATIONAL INSTITUTE ON AGING [R15AG025777] Funding Source: NIH RePORTER
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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 beta fibrillogenesis inhibition.
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