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碘催化的2-炔基苯胺与二硒醚的亲电环化反应

Iodine-catalyzed Electrophilic Cyclization of 2-Alkynylanilines with Diselenides

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【作者】 陶李明刘文奇周芸李爱桃刘卉

【Author】 TAO Li-Ming,LIU Wen-Qi,ZHOU Yun,LI Ai-Tao,LIU Hui (Hunan Provincial Key Laboratory of Xiangnan Rare-precious Metals Compounds Research and Application, Department of Chemistry and Life Science,Xiangnan University,Chenzhou 423000,China)

【机构】 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

【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.

【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.

【基金】 湖南省自然科学基金(批准号:11JJ3019);湖南省重点建设学科资金(批准号:湘教发[2011]76)资助
  • 【文献出处】 高等学校化学学报 ,Chemical Journal of Chinese Universities , 编辑部邮箱 ,2013年06期
  • 【分类号】O621.25
  • 【被引频次】1
  • 【下载频次】152
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