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Paper | Special issue | Vol 74, No. 1, 2007, pp.383-396
Published online, 20th September, 2007
DOI: 10.3987/COM-07-S(W)16
A Novel Sodium Iodide-Promoted Ring Transformation of 2-Amino-4,5-dihydro-3-furancarbonitriles to 2-Pyrrolidinones and Dihydropyrans

Hiroshi Maruoka, Fumi Okabe, and Kenji Yamagata*

*Faculty of Pharmaceutical Sciences, Fukuoka University, 8-19-1 Nanakuma, Jonan-ku, Fukuoka 814-0180, Japan

Abstract

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.