有机化学 ›› 2005, Vol. 25 ›› Issue (05): 576-578. 上一篇    下一篇

研究简报

杯芳烃多齿水杨醛亚胺衍生物的合成

蔡亚华,王云艳,颜朝国*   

  1. (扬州大学化学化工学院 扬州 225002)
  • 收稿日期:2004-04-22 修回日期:2004-11-12 发布日期:2004-04-30
  • 通讯作者: 颜朝国

Synthesis of Polydentate p-tert-Butylcalix[n]arene Salicylideneimines

CAI Ya-Hua,WANG Yun-Yan,YAN Chao-Guo*   

  1. (College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou 225002)
  • Received:2004-04-22 Revised:2004-11-12 Published:2004-04-30
  • Contact: YAN Chao-Guo

以对叔丁基杯[n]芳烃1a1b (n=6, 8)为原料, 经过三步反应, 以较高产率合成了一系列含多个水杨醛亚胺端基的西佛碱衍生物5a5f. 对叔丁基杯[n]芳烃用溴乙酸乙酯进行烃基化反应, 生成杯芳烃氧代乙酸乙酯2a2b, 后者与过量脂肪族二胺NH2(CH2)mNH2 (m=2, 4, 6)反应, 生成含有游离氨基的杯芳烃酰胺衍生物4a4f, 再与水杨醛在乙醇中反应生成目标产物席夫碱衍生物.

关键词: 杯芳烃, 席夫碱, 多齿配体, 酰胺

A series of polydentate p-tert-butylcalix[n]arene core salicylideneimine groups 5a5f were easily synthesized in good yields in three steps from the corresponding p-tert-butylcalixa[n]arenes 1a1b (n=6, 8). They were firstly alkylated with ethyl bromoacetate to give the activated ethoxycarbonylmethoxy substituted derivatives 2a2b, which were treated with excess diamines NH2(CH2)mNH2 (m=2, 4, 6) to yield the corresponding amide derivatives with free terminal amine groups 4a4f, which in turn reacted with salicylaldehyde in alcohol to afford the Schiff base products.

Key words: calixarene, amide, polydentate ligand, Schiff base