Fe-catalyzed regioselective Friedel–Crafts hydroxyalkylation of N-substituted glyoxylamide with indoles》.pdf

G Model CCLET 3447 1–6 Chinese Chemical Letters xxx (2015) xxx–xxx Contents lists available at ScienceDirect Chinese Chemical Letters jo u rn al h om epag e: ww w.els evier.c o m/lo cat e/cc let 1 2 Original article 3 Fe-catalyzed regioselective Friedel–Crafts hydroxyalkylation of 4 N-substituted glyoxylamide with indoles 5 Q1 Yang Zheng, Ren-Jun Li, Zhen Zhan, Yan Zhou, Li Hai *, Yong Wu * 6 Key Laboratory of Drug-Targeting of Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, 7 Chengdu 610041, China A R T I C L E I N F O A B S T R A C T Article history: An efficient regioselective Friedel–Crafts hydroxyalkylation of N-substituted glyoxylamide with various Received 8 July 2015 indoles catalyzed by Lewis acids was developed. The reactions proceeded smoothly at room temperature Received in revised form 17 August 2015 and the 2-hydroxy-2-(1H-indol-3-yl)-N-substituted acetamide resulted from the reactions catalyzed by Accepted 14 September 2015 FeSO4 were synthesized in excellent yields (up to 93%). While the bisindole compounds were obtained Available online xxx when FeCl3 was used as a catalyst in excellent yields (up to 92%). A possible mechanism was proposed. 2015 Chinese Chemical Soci