Abstract
A range of 2-substituted 2,3-dihydro-1H-quinolin-4-ones have been synthesized from anilines by a two-step process involving Sonogashira coupling with a propargyl alcohol then acid-catalyzed cyclization of the resulting 2-(3′-hydroxypropynyl)anilines. The cyclization reaction appears to proceed via regioselective rearrangement of the propargyl alcohol to an α,β-unsaturated ketone (Rupe rearrangement) and then 6-endo-trig ring closure (Donnelly-Farrell cyclization). The isolation of the α,β-unsaturated ketone intermediate in one example supports this pathway.
Original language | English (US) |
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Article number | G34610ST |
Pages (from-to) | 241-244 |
Number of pages | 4 |
Journal | Synlett |
Issue number | 2 |
DOIs | |
State | Published - 2011 |
Externally published | Yes |
Keywords
- Rupe rearrangement
- Sonogashira coupling
- alkaloids
- alkynes
- cyclization
- quinolinone
ASJC Scopus subject areas
- Organic Chemistry