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有机化学
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有机化学 ›› 2004, Vol. 24 ›› Issue (7): 767-769. 上一篇    下一篇

研究论文

6-氯-2(1H)-喹喔酮合成方法的改进

李荀a, 胡清萍a, 崔学桂a, 王东华*,b   

  1. a山东大学化学与化工学院 济南 250100
    b天津大学药物科学与技术学院 天津 300072
  • 收稿日期:2003-07-18 修回日期:2003-10-24 接受日期:2004-01-13 发布日期:2022-09-20
  • 通讯作者: *E-mail: wdh022@eyou.com
  • 基金资助:
    山东省自然科学基金(No. Y2002B14)资助项目

An Improved Synthesis of 6-Chloro-1H-quinoxalin-2-one

LI, Xuna, HU, Qing-Pinga, CUI, Xue-Guia, WANG, Dong-Hua*,b   

  1. a School of Chemistry & Chemical Engineering, Shandong University, Jinan250100
    b College of Pharmaceuticals & Biotechnology, Tianjin University, Tianjin300072
  • Received:2003-07-18 Revised:2003-10-24 Accepted:2004-01-13 Published:2022-09-20

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设计了以对氯苯胺和氯乙酰氯为原料,经缩合、硝化、还原、环合、氧化五步制得6-氯-2(1H)-喹喔酮的位置选择性合成方法,并对以氯乙酰氯作为苯胺的氨基保护试剂进行硝化的反应和对含活泼氯的硝基化合物进行还原的反应进行了研究.研究结果表明以氯乙酰氯作为苯胺的氨基保护试剂进行硝化的反应符合一般的硝化定位规则,而含活泼氯的硝基化合物的还原在优化条件下以铁粉为还原剂可以高选择性获得目标产物.

关键词: 喹喔酮, 对氯苯胺, 位置选择性合成

An improved regioselective synthesisof 6-chloro-1H-quinoxalin-2-one by using p-chloroaniline as a starting material was described. The synthetic steps involved condensation, nitration, reduction, cyclization, and oxidation reactions. The nitration using chloroacetic chloride as an amino protective reagent of phenylamine and reduction of nitro group accompanied by active chlorine were well studied. The result shows that the nitration reaction using chloroacetic chloride as amino protective reagentof phenylamine complies with the general rule of nitration and good selectivitycan be obtained by using iron powder as reductant in the reduction of nitro group accompanied by active chlorine.

Key words: quinoxalin-2-one, p-chloroaniline, regioselective synthesis