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

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• 作者：Tobias Harschneck ; Stefan F. Kirsch
• 刊名：Journal of Organic Chemistry
• 出版年：2011
• 出版时间：April 1, 2011
• 年：2011
• 卷：76
• 期：7
• 页码：2145-2156
• 全文大小：1122K
• 年卷期：v.76,no.7(April 1, 2011)
• ISSN：1520-6904

文摘

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 rearrangement, a condensation step, and a Br酶nsted 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.