AI Article Synopsis

  • Polycyclic ring-fused 2-pyridones were synthesized using a microwave-assisted technique that allows for efficient cyclocondensation.
  • The process starts with 3,4-dihydroisoquinolines or 3,4-dihydroharman and can produce different mono- or disubstituted variants of 2-pyridones in one step.
  • This method was also used to successfully perform a formal synthesis of the indole alkaloid sempervilam.

Article Abstract

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.

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Source
http://dx.doi.org/10.1021/ol052998eDOI Listing

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