Synthesis of multi ring-fused 2-pyridones via an acyl-ketene imine cyclocondensation
2006 (English)In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 8, no 5, 935-938 p.Article in journal (Refereed) Published
Polycyclic ring-fused 2-pyridones (5a−e and 9a−e) have been prepared via a microwave-assisted acyl-ketene imine cyclocondensation. Starting from 3,4-dihydroisoquinolines (4a−b) or 3,4-dihydroharman (8), fused 2-pyridones could be prepared in a one-step procedure. By using either Meldrum's acid derivatives (1a−d) or 1,3-dioxine-4-ones (7a−b) as acyl-ketene sources, mono- or disubstitution of the fused 2-pyridone ring could be accomplished. As an application of the method, a formal synthesis of the indole alkaloid sempervilam was performed.
Place, publisher, year, edition, pages
Washington, D.C.: American Chemical Society , 2006. Vol. 8, no 5, 935-938 p.
IdentifiersURN: urn:nbn:se:umu:diva-2714DOI: 10.1021/ol052998eOAI: oai:DiVA.org:umu-2714DiVA: diva2:140963