α,β-Unsaturated Carboxylic Acid Derivatives. VIII. The Synthesis and Reaction of Esters <I>N</I>-Acyl-<I>N</I>-bromo-α-dehydroamino Acid

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概要

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• The addition of bromine to <I>t</I>-butyl 2-(<I>N</I>-acylamino)-2-alkenoate (<B>3</B>) was accompanied by the elimination of hydrogen bromide and the decomposition of the ester group to give 2-(<I>N</I>-acylamino)-3-bromo-2-alkenoic acid, while the bromination of <B>3</B> with NBS gave the corresponding <I>N</I>-bromo derivative (<B>7</B>), whose bromine atom gradually migrates to give <I>t</I>-butyl 2-(<I>N</I>-acylamino)-3-bromo-2-alkenoate. The substitution of the bromine of <B>7</B> with nucleophiles gave, successively, the corresponding <I>N</I>-methoxy, <I>N</I>-benzyloxy and <I>N</I>-cyano derivatives, while that with sodium azide gave the corresponding migration products. The structures of the new compounds were assigned.

• 公益社団法人 日本化学会の論文

著者

• Yoshimura Juji

  Laboratorium für Organische Chemie Technische Hochschule Tokyo

• Sato Yoshiaki

  Laboratory of Organic Chemistry, Faculty of Technology, Kanagawa University

• 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

• Nishino Takashi

  Laboratory of Organic Chemistry, Faculty of Technology, Kanagawa University

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