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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| Authors: | Virender Singh Prakas R Maulik |
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| Institution: | a Medicinal and Process Chemistry Division, Central Drug Research Institute, PO Box 173, Lucknow 226001, India
b Molecular and Structural Biology Division, Central Drug Research Institute, PO Box 173, Lucknow 226001, India |
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| Abstract: | The synthesis of substituted 3-methylene-2-pyridones via SN2 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. |
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| Keywords: | Baylis-Hillman 2-Pyridone SN2 reaction Spiroisoxazoline |
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