4.7 Article

One-Pot Synthesis of 1,2-Dihydropyridines: Expanding the Diverse Reactivity of Propargyl Vinyl Ethers

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JOURNAL OF ORGANIC CHEMISTRY
卷 76, 期 7, 页码 2145-2156

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AMER CHEMICAL SOC
DOI: 10.1021/jo102545m

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  1. Deutsche Forschungsgemeinschaft (DFG)
  2. Fonds der Chemischen Industrie (FCI)
  3. TUM Graduate School

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The catalyzed synthesis of 1,2-dihydropyridines starting from easily accessible propargyl vinyl ethers was realized. The reaction sequence involving a transition metal-catalyzed propargyl-Claisen re-arrangement; a condensation step, and a Bronsted acid-catalyzed heterocyclization furnishes the highly substituted heterocycles in moderate to excellent yields. Additionally, a practical one-pot protocol toward 1,2-dihydropyridines and 2H-pyrans starting from propargylic alcohols was developed.

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