Oxidation of 2,6-piperazinediones.
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概要
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1,4-Disubstituted 2,6-piperazinediones (<B>1</B>) are susceptible to oxidation at the methylene group in the piperazine ring, giving piperazinetetrone (<B>4</B>) on being treated with selenium dioxide in boiling dioxane. Treatment of 1,4-diphenyl-2,6-piperazinedione (<B>1a</B>) with either nitrobenzene or tosyl chloride and triethylamine in benzene gives cyclic dimer (<B>9</B>) of dehydrogenated <B>1a</B>. Cycloadduct (<B>10</B>) is obtained in the presecne of <I>N</I>-phenylmaleimide. It seems that both <B>9</B> and <B>10</B> are formed <I>via</I> labile mesoionic intermediate (<B>8</B>). Piperazinedione (<B>1a</B>) reacted with tosyl chloride, pyridine, and benzoyl chloride to give mesoionic compound (<B>11</B>) having 3-benzoyl and 5-(<I>p</I>-tolylthio) groups.
- 公益社団法人 日本化学会の論文
著者
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Tanaka Tatsuo
Department Of Analytical Chemistry Showa Pharmaceutical University
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Yamazaki Hiroaki
Department of Industrial Chemistry, Faculty of Engineering, Ibaraki University
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Ohta Masaki
Department of Chemistry, Faculty of Science, Tokyo Institute of Technology
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