Wang Xinyue, Zeng Heyang, Zhang Wenli, Guo Haiyang, Jin Tao, Shi Senlei, Jin Xiaoyuan, Qu Na, Liu Li, Zhang Lianpeng
Yunnan Key Laboratory of Wood Adhesive and Glued Products, Southwest Forestry University, Kunming 650224, Yunnan, China.
College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing 314001, Zhejiang, China.
Org Biomol Chem. 2022 Oct 19;20(40):7949-7955. doi: 10.1039/d2ob01488b.
Substituted benzo[]indoles are one of the most attractive frameworks because of their wide range of biological and optical activities. Herein, a copper-catalyzed one-step synthesis of biologically important polysubstituted benzo[]indoles starting from 8-alkynyl-1-naphthylamine derivatives is reported. In this protocol, many substituents tolerated the reaction conditions and produced ()-benzo[]indoles in good yields. Preliminary mechanistic studies indicated that the reaction proceeds a stereoselective intramolecular -addition and S-Ar reaction with high selectivity and high yields. The synthesized polysubstituted ()-benzo[]indoles possess sulfonamide building blocks, which make them candidates for bioactive molecules.
取代苯并[ ]吲哚是最具吸引力的骨架之一，因其具有广泛的生物活性和光学活性。本文报道了一种从8-炔基-1-萘胺衍生物出发，铜催化一步合成具有重要生物学意义的多取代苯并[ ]吲哚的方法。在该反应体系中，许多取代基都能耐受反应条件，并以良好的产率生成( )-苯并[ ]吲哚。初步机理研究表明，该反应通过立体选择性分子内 -加成和S-Ar反应进行，具有高选择性和高收率。合成的多取代( )-苯并[ ]吲哚含有磺酰胺结构单元，这使其成为生物活性分子候选物。
