中华医学超声杂志

应用化学 ›› 2009, Vol. 26 ›› Issue (09): 1120-1122.

• 研究简报 • 上一篇    下一篇

微波促进下4-乙炔基苯磺酰胺的“一锅法”合成

张文生1,2,匡春香1*   

  1. (1.同济大学化学系 上海 200092;2.焦作师范高等专科学校化学系 焦作)
  • 收稿日期:2008-09-04 修回日期:2008-10-30 出版日期:2009-09-10 发布日期:2009-09-10
  • 通讯作者: 匡春香，男，教授、博士生导师; E-mail:kuangcx@mail.tongji.edu.cn; 研究方向：精细有机合成及金属有机化学
  • 基金资助:
    上海市自然科学基金(06ZR14085)资助项目

Microwave-induced one-pot synthesis of 4-ethynylbenzenesulfonamide

ZHANG Wen-Sheng1,2,KUANG Chun-Xiang1*   

  1. (1.Department of Chemistry,Tongji University,Shanghai 200092;
    2.Department of Chemistry,Jiaozuo Teachers′ College,Jiaozuo)
  • Received:2008-09-04 Revised:2008-10-30 Published:2009-09-10 Online:2009-09-10

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摘要：

以3-(4-氯磺酰苯基)-2，3-二溴丙酸和氨水（2.2 eq）为原料，以 DMF为溶剂，经微波辐射25 s，磺酰胺化和脱溴脱羧反应可同步进行，立体选择性地合成中间体(Z)-4-(2-溴乙烯基)苯磺酰胺；该中间体不需分离，直接向反应体系中加入1,8-二氮杂环[5,4,0]十一烯-7 (DBU，2eq)，再微波辐射1 min，“一锅法”得到4-乙炔基苯磺酰胺，并通过1H NMR和13C NMR和IR进行了表征，收率达70%。

关键词: 磺酰胺, 苯乙炔, 一锅法, 微波辐射

Abstract:

One-pot simultaneous debrominative decarboxylation and sulfamation of anti-3-(4-chlorosulfonyl-benzyl)-2, 3-dibromopropanoic acid in DMF using aqueous ammonia (2.2 eq) under microwave irradiation condition for 25s stereoselectively afforded intermediate (Z)-4-(2-brompvinyl)benzenesulfonamides. The intermediates, without isolation and purification, were treated with 1,8-diazabicyclo[5.4.0]undec-7-ene ( DBU, 2 eq) under microwave irradiation condition for 1 min to give the desired 4-ethynylbenzenesulfonamide in a yield of 70%. The structure of the product was identified by 1H NMR, 13CNMR and IR.

Key words: sulfonamide, ethynylbenzene, one-pot, microwave irradiation

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