Citation: Yang Zheng, Ren-Jun Li, Zhen Zhan, Yan Zhou, Li Hai, Yong Wu. Fe-catalyzed regioselective Friedel-Crafts hydroxyalkylation of N-substituted glyoxylamide with indoles[J]. Chinese Chemical Letters, ;2016, 27(01): 41-46. doi: 10.1016/j.cclet.2015.09.023 shu

Fe-catalyzed regioselective Friedel-Crafts hydroxyalkylation of N-substituted glyoxylamide with indoles

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Key Laboratory of Drug-Targeting of Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu 610041, China

Corresponding author: Li Hai, Yong Wu,
Received Date: 8 July 2015
Available Online: 17 August 2015
Fund Project: We sincerely thank the National Natural Science Foundation of China(Nos. 21472130, 81373259) for financial support of this study. (Nos. 21472130, 81373259)

An efficient regioselective Friedel-Crafts hydroxyalkylation of N-substituted glyoxylamide with various indoles catalyzed by Lewis acids was developed. The reactions proceeded smoothly at room temperature and the 2-hydroxy-2-(1H-indol-3-yl)-N-substituted acetamide resulted from the reactions catalyzed by FeSO₄ were synthesized in excellent yields(up to 93%). While the bisindole compounds were obtained when FeCl₃ was used as a catalyst in excellent yields(up to 92%). A possible mechanism was proposed.
- Friedel-Crafts hydroxyalkylation,
- N-substituted glyoxylamide,
- Indole,
- Lewis acid,
- 2-Hydroxy-2-(1H-indol-3-yl)-N-substituted acetamide,
- Bisindole compounds
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