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- W2903882056 abstract "Abstract The synthesis of 3‐alkyliden‐2,3‐dihydro‐4‐quinolones has been accomplished in a domino fashion through a three‐step sequence that comprised an initial aza‐Baylis‐Hillman reaction, followed by a 1,3‐rearrangement and an intramolecular amination. Starting from readily available aryl vinyl ketones and N ‐tosyl imines, the reaction with PPh 3 , CsOAc and CuI in CH 3 CN gave rise, in good overall yields, to final 3‐alkyliden‐4‐quinolone derivatives, valuable scaffolds in medicinal chemistry. The simultaneous addition of two bases, PPh 3 and CsOAc, was found to be crucial for the success of the process. While PPh 3 promoted the reversible aza‐Baylis‐Hillman reaction, CsOAc triggered the subsequent 1,3‐rearrangement, which shifted the initial equilibrium and allowed to complete the synthetic sequence upon the addition of CuI. magnified image" @default.
- W2903882056 created "2018-12-22" @default.
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- W2903882056 date "2019-01-23" @default.
- W2903882056 modified "2023-10-09" @default.
- W2903882056 title "Domino Synthesis of 3-Alkyliden-2,3-Dihydro-4-Quinolones" @default.
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- W2903882056 doi "https://doi.org/10.1002/adsc.201801490" @default.
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