有机化学 ›› 2008, Vol. 28 ›› Issue (04): 750-754. 上一篇    下一篇

研究简报

微波辐射下合成3-芳基-9-氨基-1,2,3,4-四氢吖啶-1-酮衍生物

韩光范*,董军科,汪芳明,邢正,赵玉媛   

  1. (江苏科技大学材料科学与工程学院 镇江 212003)
  • 收稿日期:2007-07-02 修回日期:2007-10-30 发布日期:2008-04-17
  • 通讯作者: 韩光范

Synthesis of 3-Aryl-9-amino-1,2,3,4-tetrahydroacridin-1-one Derivatives under Microwave Irradiation

HAN Guang-Fan*,DONG Jun-Ke,WANG Fang-Ming,XING Zheng,ZHAO Yu-Yuan   

  1. (School of Materials Science and Engineering, Jiangsu University of Science and Technology, Zhenjiang 212003)
  • Received:2007-07-02 Revised:2007-10-30 Published:2008-04-17
  • Contact: HAN Guang-Fan

在微波辐射和对甲基苯磺酸的催化作用下, 5-芳基-1,3-环己二酮与邻氨基苯甲腈进行缩合反应, 得到了N-取代的2-氨基苯甲腈衍生物, 在K2CO3和Cu2Cl2的催化作用下进一步合环, 得到3-芳基-9-氨基-1,2,3,4-四氢吖啶-1-酮衍生物, 用LiAlH4还原羰基得到3-芳基-9-氨基-1,2,3,4-四氢吖啶-1-醇衍生物. 新合成化合物的结构均经元素分析、红外光谱和核磁共振光谱予以确认.

关键词: 5-芳基-1,3-环己二酮, 吖啶酮衍生物, 合成, 微波辐射

Under microwave irradiation and using p-toluenesulfonic acid as a catalyst, the condensation reaction of 5-aryl-1,3-cyclohexanediones with o-anthranilonitrile afforded the corresponding N-substituted-2- aminobenzonitriles, which were followed by the intramolecular cyclization in the presence of potassium carbonate and cuprous chloride to give 3-aryl-9-amino-1,2,3,4-tetrahydroacridin-1-one. Then reduction of these acridinone compounds with lithium aluminum hydride in the ethyl ether afforded 3-aryl-9- amino-1,2,3,4-tetrahydroacridin-1-ol derivatives. The structures of all these new compounds were characterized by elemental analysis, IR and 1H NMR and 13C NMR spectra.

Key words: derivative of acridinone, microwave irradiation, 5-aryl-1,3-cyclohexanedione, synthesis