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Short Paper | Special issue | Vol 88, No. 1, 2014, pp.639-650
Published online, 1st July, 2013
DOI: 10.3987/COM-13-S(S)18
Expedient Synthesis of 2-Oxopiperazines Using a SN2 / Cope-Type Hydroamination Sequence

Nicolas Das Neves, Michaël Raymond, and André M. Beauchemin*

*Department of Chemistry, University of Ottawa, Ottawa Ontario, K1N 6N5, Canada

Abstract

An approach for the synthesis of 2-oxopiperazines from allylic 2-iodoacetamides and aqueous NH2OH has been developed. The reaction proceeds through a SN2 / intramolecular Cope-type hydroamination sequence yielding in 2-oxopiperazines with moderate to good yield.