高等学校化学学报 ›› 1983, Vol. 4 ›› Issue (1): 100.

• 论文 • 上一篇    下一篇

一氰乙基化β-二酮的合成及其异构化

黄化民, 李葆, 战永复   

  1. 1. 吉林大学化学系;
    2. 吉林师范学院化学系
  • 收稿日期:1981-10-15 出版日期:1983-02-24 发布日期:1983-02-24

MONOCYANOETHYL-β-DIKETONES AND THEIR ISOMERIZATION

Huang Huamin, Li Bao, Zhan Yongfu   

  1. 1. Department of Chemistry, Jilin University, Changchun;
    2. Department of Chemistry, Jilin Teacher's College, Jilin
  • Received:1981-10-15 Online:1983-02-24 Published:1983-02-24

摘要: 本文通过β-二酮与丙烯腈反应合成了三个二酮的一氰乙基化合物:4-乙酰基-5-氧代己腈(Ⅰ),4-乙酰基-5-氧代庚腈(Ⅱ)及4-苯甲酰基-5-氧代已腈(Ⅲ).(Ⅰ)—(Ⅲ)环合得到了三个未饱和内酰胺:5-乙酰基-6-甲基3,4-二氢化-2(1H)吡啶酮(Ⅳ),5-丙酰基-6-甲基3,4-二氢化-2(1H)吡啶酮(Ⅴ),5-苯甲酰基-6-甲基3,4-二氢化-2(1H)吡啶酮(Ⅵ)。(Ⅰ)—(Ⅲ)和(Ⅳ)—(Ⅵ)水解得到了相应的酮酸:4-乙酰基-5-氧代已酸(Ⅶ),4-乙酰基-5-氧代庚酸(Ⅷ),和4-苯甲酰基-5-氧代已酸(Ⅸ)。(Ⅳ)—(Ⅵ)与2,4-二硝基苯肼反应得到了相应的酮腙(Ⅹ)—(Ⅻ)。以上化合物中(Ⅱ)、(Ⅲ)、(Ⅴ)、(Ⅵ)、(Ⅷ)、(Ⅸ)、(Ⅹ)、(Ⅺ)、(Ⅻ)是未知物。

Abstract: β-Diketones (acetylacetone, propionylacetone and benzoylacetone) were treated with acrylonitrile in the presence of aqueous potassium hydroxide giving monocyanoethylated β-diketones (Ⅰ)-(Ⅲ), which by heating with HCl were isomerized to the corresponding3,4-dihydro-2-(lH) pyrid-ones(Ⅳ)-(Ⅵ). (Ⅰ)-(Ⅲ) and (Ⅳ)-(Ⅵ) were hydrolyzed to the ketoacids (Ⅶ)-(Ⅸ). 2,4-Dinitrophenylhydrazones(Ⅹ)-(Ⅻ) were prepared from(Ⅳ) -(Ⅵ). Compounds (Ⅱ), (Ⅲ), (Ⅴ), (Ⅵ)and(Ⅷ)-(Ⅶ) were reported for the first time.

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