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Paper | Regular issue | Vol 68, No. 3, 2006, pp.465-474
Published online, 14th February, 2006
DOI: 10.3987/COM-05-10568
Synthesis and X-Ray Crystal Structure Determinations of Pyrrolidine-2,4-diones, 2-Iminopyrrolidin-5-ones and 1,3-Oxazine-2,4-diones Derived from Acetoacetanilides

Thomas Duff, John P. James,* and Helge Müller-Bunz

*School of Chemical Sciences, Dublin City University, Glasnevin, Dublin 9, Ireland

Abstract

Commercially available acetoacetanilides may, after initial alkylation, be cyclized to pyrrolidine-2,5-diones by reaction with ethyl bromoacetate or cyclized to 5-iminopyrrolidin-2-ones with chloroacetonitrile. Reaction with ethyl chloroformate gives 1,3-oxazine-2,4-diones. Several examples of these reactions using different alkyl groups are described. The structures of the products were confirmed by X-Ray crystallography.