有机化学 ›› 2013, Vol. 33 ›› Issue (03): 630-633.DOI: 10.6023/cjoc201210038 上一篇    下一篇

研究简报

一种阿片受体样受体配体3-[4-(2,6-二氯苯基)哌啶甲基]-2-(噻吩-2)基吲哚的实用合成

程绎南, 谢桂英, 孙淑君, 游秀峰   

  1. 河南农业大学植保学院 郑州 450002
  • 收稿日期:2012-10-19 修回日期:2012-12-05 发布日期:2012-12-20
  • 通讯作者: 程绎南 E-mail:chyn212@yahoo.com.cn

A Practical Synthesis of 3-{[4-(2,6-Dichlorophenyl)piperidin-1-yl]- methyl}-2-(thiophen-2-yl)-1H-indole as a New Ligand for Opioid Receptor Like 1 Receptor

Cheng Yinan, Xie Guiying, Sun Shujun, You Xiufeng   

  1. Plant Protection College, Henan Agricultural University, Zhengzhou 450002
  • Received:2012-10-19 Revised:2012-12-05 Published:2012-12-20

3-[4-(2,6-二氯苯基)哌啶甲基]-2-(噻吩-2)基吲哚作为一种新的阿片受体样受体配体以商业化原料苯肼(2), 2-乙酰基噻吩(3), 2,6-二氯苯硼酸(5)和4-溴吡啶(6)为原料通过四步反应而得. 该合成方法具有所涉及反应媒介便于回收利用、中间体分离纯化简单、废弃物产生少和收率高(总收率65%)等绿色合成特点, 具有潜在规模生产和应用前景.

关键词: 取代吲哚, 合成, 催化氢化, 缩合

3-{[4-(2,6-Dichlorophenyl)piperidin-1-yl]methyl}-2-(thiophen-2-yl)-1H-indole (1) as a ligand for opioid receptor like 1 receptor was prepared via four steps from commercially available phenylhydrazine (2), 1-(thiophen-2-yl)- ethanone (3), 2,6-dichloro- phenyl-boronic acid (5) and 4-bromopyridine (6). This convenient approach was green and had potential application for the scale production because of recoverable reaction medium, simple isolating process of intermedi-ates, little waste and highly total yield of 65%.

Key words: substituted indole, synthesis, catalytic hydrogenation, condensation