Synthesis and photoreaction of D-nor-5.ALPHA.-androstan-16-one acetylhydrazone in the presence of oxygen.

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概要

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• <I>D</I>-Nor-5α-androstan-16-one was prepared <I>via</I> seven steps from 16-diazo-3β-hydroxyandrost-5-en-17-one. The major products of the photolysis of its acetylhydrazone in dioxane containing oxygen were the parent ketone and 17-oxa-5α-androstan-16-one, accompanied by low yields of three isomeric lactams: 17-aza-5α-androstan-16-one, 16-aza-5α-androstan-17-one, and 17-aza-5α,13α-androstan-16-one. These three are the same lactams formed in the photo-Beckmann rearrangement of the corresponding oxime, <I>D</I>-nor-5α-androstan-16-one oxime. Their formation from the acetylhydrazone may have some mechanistic significance with regard to the path of the formation of lactams in the photolysis of 5α-androstan-17-one acetylhydrazone in the presence of oxygen reported previously. The mass spectrometric fragmentations of fifteen <I>D</I>-nor-5α-androstanes with functional groups at their C-16 positions are described.

• 公益社団法人 日本化学会の論文

著者

• Masamune Tadashi

  Department of Chemistry, Faculty of Science, Hokkaido University

• Masamune Tadashi

  Department Of Chemistry Faculty Of Science Hokkaido University

• Uchida Tsutomu

  Department Of Applied Physics Faculty Of Engineering Hokkaido University

• Suginome Hiroshi

  Department of Chemistry, Faculty of Science

• Kizuka Kazuhiko

  Department of Chemistry, Faculty of Science, Hokkaido University

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