Synthesis of substituted 3-methylene-2-pyridones from Baylis–Hillman derivatives and its application for the generation of 2-pyridone substituted spiroisoxazolines

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• 作者：Virender Singh ; Gaya P. Yadav ; Prakas R. Maulik ; Sanjay Batra
• 关键词：Baylis– ; Hillman ; 2-Pyridone ; S_N2 reaction ; Spiroisoxazoline
• 刊名：Tetrahedron
• 出版年：2008
• 出版时间：24 March 2008
• 年：2008
• 卷：64
• 期：13
• 页码：2979-2991
• 全文大小：432 K

文摘

The synthesis of substituted 3-methylene-2-pyridones via S_N2 displacement reaction of nucleophiles bearing a keto group on the acetyl derivative of Baylis–Hillman adducts of acrylonitrile followed by TFA/H₂SO₄-mediated intramolecular cyclization is described. The utility of these pyridone derivatives for the synthesis of new spiroisoxazolines in highly regio- and stereo-selective fashion is also illustrated. The structure of the spiroisoxazolines has been secured via X-ray crystallographic analysis.