有机化学 ›› 2011, Vol. 31 ›› Issue (03): 362-364. 上一篇    下一篇

研究简报

6-甲氧基-1,2,3,9-四氢-4H-咔唑-4-酮肟的一锅合成

孙健,盛源,谢琼*,仇缀百   

  1. (复旦大学药学院药物化学教研室 上海 201203)
  • 收稿日期:2010-06-29 修回日期:2010-09-30 发布日期:2010-10-11
  • 通讯作者: 谢琼 E-mail:xiejoanxq@gmail.com

One-Pot Synthesis of 6-Methoxy-1,2,3,9-tetrahydro-4H- carbazol-4-one Oxime

SUN Jian, SHENG Yuan, XIE Qiong, CHOU Zhui-Bai   

  1. (Department of Medicinal Chemistry, School of Pharmacy, Fudan University, Shanghai 201203)
  • Received:2010-06-29 Revised:2010-09-30 Published:2010-10-11
  • Contact: Qiong XIE E-mail:xiejoanxq@gmail.com

报道了6-甲氧基-1,2,3,9-四氢-4H-咔唑-4-酮肟(3b)的一锅合成法, 将Fischer吲哚合成与肟化两步反应并为一步, 可简化操作, 提高收率. 反应可以在弱碱性且温度温和的条件下一锅合成, 是由于肟化使Fischer吲哚环合变得容易, 羰基与肟基在互变异构方向上的差别是影响环合反应的关键因素.

关键词: 一锅合成, Fischer吲哚合成, 肟化, 互变异构

6-Methoxy-1,2,3,9-tetrahydro-4H-carbazol-4-one oxime (3b) was synthesized by one-pot reaction. The combination of Fischer indole synthesis and oximation led to simplified process and increased productivity. This reaction could proceed in one pot in weak alkaline solution at mild temperature since oximation has facilitated the Fischer indole cyclization. Differences in tautomerization between carbonyl and oximyl were considered as the key factor that influenced the cyclization.

Key words: one-pot synthesis, Fischer indole synthesis, oximation, tautomerism

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