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Communication | Special issue | Vol 33, No. 1, 1992, pp.91-95
Published online, 1st January, 1970
DOI: 10.3987/COM-91-S26
Anionic Hetero[3,3]rearrangement. N-Acyl-N'-enylhydrazines to Pyrrolidinones

Yasuyuki Endo* and Koichi Shudo

*Faculty of Pharmaceutical Sciences, University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113, Japan

Abstract

N -Acyl-N ’-enylhydrazines rearrange upon treatment with base to afford
5-amino-2-pyrrolidinones. The rearrangement can be rationalized in terms of
initial stereospecific [3,3]sigmatropic shifts of the enolates followed by
intramolecular addition of the nitrogen atom of the amide group to the imino
group.