A Novel Sodium Iodide-Promoted Ring Transformation of 2-Amino-4,5-dihydro-3-furancarbonitriles to 2-Pyrrolidinones and Dihydropyrans

@article{Maruoka2007ANS,
  title={A Novel Sodium Iodide-Promoted Ring Transformation of 2-Amino-4,5-dihydro-3-furancarbonitriles to 2-Pyrrolidinones and Dihydropyrans},
  author={Hiroshi Maruoka and Fumi Okabe and Kenji Yamagata},
  journal={Heterocycles},
  year={2007},
  volume={74},
  pages={383-396}
}
A novel and efficient approach to 2-pyrrolidinones and dihydropyrans via the ring transformation of 3-phenacylated tetrahydro-2-imino-3-furancarbonitriles in the presence of sodium iodide is described. The key feature in the ring transformation is that C-phenacylation of 2-amino-4,5-dihydro-3-furancarbonitriles using phenacyl bromides, e.g. phenacyl bromide, 4-chlorophenacyl bromide and 4-methoxyphenacyl bromide, proceeds smoothly and the ring-opening intermediate having leaving group such as… CONTINUE READING

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