Syntheses and Reactions of Nitrogen- and Sulfur-Analogs of 2-Piperazinone

Abstract 2-Piperazinone oxime, 2-piperazinoneimine, and 2-piperazinethione were synthesized. The reaction mixture of ethylenediamine and glycolonitrile was treated with an excess amount of hydroxylamine in methanol to give 2-piperazinone oxime in a 53% yield. 2-Piperazinone oxime was easily reduced to 2-piperazinoneimine, which was then treated with hydrogen sulfide to yield 2-piperazinethione. Some reactions of these compounds are described.