Chinese Journal of Organic Chemistry >
N-Iodosuccinimide (NIS) Promoted Synthesis of 3-Substituted Indole Derivatives
Received date: 2022-02-16
Revised date: 2022-04-04
Online published: 2022-05-07
Supported by
National Natural Science Foundation of China(21801218)
A catalytic procedure for Michael addition reaction of indole or its derivatives with α,β-unsaturated ketones catalyzed by N-halosuccinimide has been successfully developed. Firstly, the Michael addition reaction of indole with chalcone was used as the template reaction, and the optimal conditions of the reaction were explored. The experimental results show that the optimal condition employs 10 mol% N-iodosuccinimide (NIS) as catalyst, CH3CN as solvent, room temperature as reaction temperature and 18 h as reaction time. Under this optimized conditions, the reaction of chalcone and its derivatives with various α,β-unsaturated ketone can proceed smoothly to obtain the aimed product. The yields of these reactions ranged from 51% to 90%. The reaction conditions are mild and the reaction operation is simple.
Key words： N-iodosuccinimide (NIS); catalysis; indole; α,β-unsaturated ketone; Michael addition
Cunwei Qian , Rong Han , Zhixing Shen , Qian Li , Xuanrong Chen . N-Iodosuccinimide (NIS) Promoted Synthesis of 3-Substituted Indole Derivatives[J]. Chinese Journal of Organic Chemistry, 2022 , 42(8) : 2496 -2503 . DOI: 10.6023/cjoc202202020
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