A NOVEL SODIUM IODIDE-PROMOTED RING TRANSFORMATION OF 2-AMINO-4,5-DIHYDRO-3-FURANCARBONITRILES TO 2-PYRROLIDINONES AND DIHYDROPYRANS

摘要

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 iodide ion is produced.