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Convenient Synthesis of Acrylanilides via K2CO3-Mediated Deacylative Olefination of Acetoacetanilides
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DOI：10.1002/ajoc.70488.png)
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Abstract
En 中文
A new and stereoselective E-olefination strategy has been developed utilizing potassium carbonate (K2CO3) as a mild and environmentally benign base. This protocol enables the transformation of β-ketoamides and aldehydes into the valuable acrylanilides through an acyl bond cleavage. The process involves initial enolate formation, followed by an aldol-type addition that proceeds through deacetylation to generate the desired C═C bond with elimination of byproduct. This metal-free, and mild base-promoted protocol provides a wide substrate scope with stereoselectivity and good to excellent yields, demonstrating a synthetically valuable route for acrylanilides synthesis and thereby for accessing several active pharmaceutical ingredients with potential acceleration in drug discovery efforts, having minimized ecological impact.
Keywords:
acrylanilides
E-olefination
potassium carbonate (K2CO3)
stereoselective
β-ketoamides
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