Synthesis of Carbazoles via One‐Pot Copper‐Catalyzed Amine Insertion into Cyclic Diphenyleneiodoniums as a Strategy to Generate a Drug‐Like Chemical Library
Synthesis of Carbazoles via One‐Pot Copper‐Catalyzed Amine Insertion into Cyclic Diphenyleneiodoniums as a Strategy to Generate a Drug‐Like Chemical Library
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DOI：
10.1002/adsc.201300271
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发表时间：
2013-08
影响因子：
5.4
通讯作者：
Daqian Zhu;Qi Liu;Bingling Luo;Meihui Chen;R. Pi;Peng-mian Huang;S. Wen
中科院分区：
文献类型：
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作者：
Daqian Zhu;Qi Liu;Bingling Luo;Meihui Chen;R. Pi;Peng-mian Huang;S. Wen
咔唑类化合物因其独特的结构特征和潜在的药理活性而引起了合成化学家的高度兴趣。与线性芳基碘鎓相比，环状二亚苯基碘鎓更具惰性，并且其作为结构单元的应用并未引起太多关注。采用我们的合成策略，可以在温和的条件下从单一环状二亚苯基碘鎓有效地获得多样化的咔唑。由乙酸铜(II)催化的反应以中等至良好的收率提供了多种咔唑与多种胺，包括苯胺、脂肪胺和磺酰胺。此外，获得的其中一种咔唑表现出出色的保护HT-22神经元细胞免受神经毒素谷氨酸和同型半胱氨酸引起的损伤的能力。
Carbazoles have attracted high interest among synthetic chemists due to their unique structural features and potential pharmacological activities. Compared to linear aryliodoniums, cyclic diphenyleneiodoniums are more inert and have not attracted much attention to their application as building blocks. Employing our synthetic strategy, diversified carbazoles can be efficiently obtained from a single cyclic diphenyleneiodonium under mild conditions. The reactions catalyzed by copper(II) acetate have provided a variety of carbazoles in modest to good yields with a broad range of amines including anilines, aliphatic amines and sulfonamides. Moreover, one of the obtained carbazoles has displayed an outstanding ability to protect HT‐22 neuronal cells from the damage induced by neurotoxins glutamate and homocysteic acid.