高等学校化学学报

高等学校化学学报 ›› 2013, Vol. 34 ›› Issue (6): 1423.doi: 10.7503/cjcu20120971

• 有机化学 • 上一篇    下一篇

碘催化的2-炔基苯胺与二硒醚的亲电环化反应

陶李明, 刘文奇, 周芸, 李爱桃, 刘卉   

  1. 湘南学院化学与生命科学系, 湘南稀贵金属配合物及其医药研究湖南省重点实验室, 郴州 423000
  • 收稿日期:2012-10-26 出版日期:2013-06-10 发布日期:2013-05-07
  • 通讯作者: 陶李明,女,副教授,主要从事有机催化合成方面的研究.E-mail:taoliming2005@yahoo.com.cn E-mail:taoliming2005@yahoo.com.cn
  • 基金资助:

    湖南省自然科学基金(批准号: 11JJ3019)和湖南省重点建设学科资金(批准号: 湘教发[2011]76)资助.

Iodine-catalyzed Electrophilic Cyclization of 2-Alkynylanilines with Diselenides

TAO Li-Ming, LIU Wen-Qi, ZHOU Yun, LI Ai-Tao, LIU Hui   

  1. Hunan Provincial Key Laboratory of Xiangnan Rare-precious Metals Compounds Research and Application, Department of Chemistry and Life Science, Xiangnan University, Chenzhou 423000, China
  • Received:2012-10-26 Online:2013-06-10 Published:2013-05-07

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摘要：

研究了碘催化的2-炔基苯胺与二硒醚的亲电环化反应. 结果表明, 在碘单质(0.2 mmol)、 2-炔基苯胺(0.2 mmol)、 二硒醚(0.1 mmol)和甲苯(2 mL)共存体系中, 反应温度为110℃时, 2-炔基苯胺与二硒醚能发生亲电环化反应, 生成相应的3-硒取代吲哚化合物, 产率为中等到良好. 该反应在无金属催化的条件下进行, 为合成官能团吲哚提供了一种新途径.

关键词: 碘, 2-炔基苯胺, 二硒醚, 亲电环化反应

Abstract:

Indoles, particularly 3-selenenylindoles, are important compounds found in a wide range of biologically active compounds and natural products, as well as are useful building blocks in organic synthesis. For the reasons, a new and efficient method for the selective synthesis of 3-selenenylindoles was developed by electrophilic iodocyclization of 2-alkynylanilines with diselenides. In the presence of I2 and toluene, a variety of 2-alkynylanilines selectively underwent the electrophilic cyclization with diselenides leading to the corresponding 3-selenenylindoles in moderate to excellent yields. Importantly, these reactions were conducted under metal-free conditions, and will open a new door to functionalized indoles synthesis.

Key words: Iodine, 2-Alkynylaniline, Diselenide, Electrophilic cyclization

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