α,β-Unsaturated Carboxylic Acid Derivatives. IX. The Cyclization of α-(<I>N</I>-Acyl-hydroxyamino) Acid Esters with Ammonia or Hydroxylamine

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概要

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• A new type of cyclization reaction of α-(<I>N</I>-acyl-hydroxyamino) acid esters to imidazolidine-4-one derivatives and the synthesis of several 2,5-piperazinedione derivatives are described. The treatment of β-methoxy-α-(<I>N</I>-chloroacetyl- or <I>N</I>-phthaloylglycyl-hydroxyamino) acid esters with ammonia gave 2-carbamoyl-2-(1-methoxy)alkyl-or aralkyl-imidazolidine-4-ones, while a similar cyclization of α-(<I>N</I>-haloacetylamino) or α-(<I>N</I>-haloacyl-hydroxyamino) acid esters with ammonia or hydroxylamine gave 2,5-piperazinedione, 1-hydroxy-2,5-piperazinedione or 1,4-dihydroxy-2,5-piperazinedione derivatives. The difference in the formation mechanisms between the imid-azolidine-4-one and 2,5-piperazinedione and their structural assignment were discussed.

• 公益社団法人 日本化学会の論文

著者

• Kato Masaki

  Laboratory For Biolinguistics Riken Brain Science Institute

• Yoshimura Juji

  Laboratorium für Organische Chemie Technische Hochschule Tokyo

• Shin Chung-gi

  Laboratory of Chemistry for Natural Products, Faculty of Science, Tokyo Institute of Technology

• Nanjo Katsumi

  Laboratory of Organic Chemistry, Faculty of Technology, Kanagawa University

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