Structure of reaction products of 5-nitrosotropolone and arylamine.

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概要

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• The structures of abnormal reaction products (1:1 and 1:2) between 5-nitrosotropolone and arylamine are elucidated. The reaction of 5-nitrosotropolone with arylamine (e.g., aniline and <I>p</I>-toluidine) affords initially a bicyclic addition product, having 8-azabicyclo[3.2.1]octane system which could be formed by the attack of the amine on 4- and 1-positions of the tropolone ring. The adduct contains two isomers having <I>syn</I> and <I>anti</I> configuration with respect to the hydroxyimino group. These adducts easily isomerized under alkaline conditions to form lactams having the 6-azabicyclo[3.2.1]octane system, which may have been resulted from skeletal rearrangement of a seven-membered ring to a six-membered one. The former adducts, the 8-azabicyclo[3.2.1]octane system, further react with another mole of arylamine to give 1:2 products containing a lactam moiety via similar skeletal rearrangement.

• 公益社団法人 日本化学会の論文

著者

• Nozoe Tetsuo

  Department of Chemistry Faculty of Science Tohoku University

• Asao Toyonobu

  Department of Chemistry Faculty of Science Tohoku University

• Imajo Seiichi

  Suntory Institute for Bioorganic Research

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