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AlCl?·6H?O-Catalyzed Friedel-Crafts Alkylation of Indoles by the para-Quinone Methide Moiety of Celastrol.

ABSTRACT: A classical Friedel-Crafts alkylation of different indoles catalyzed by AlCl?·6H?O has been developed for a well-known important natural product, celastrol, resulting in a series of derivatives for further biological evaluation. The catalyst loading was reduced to 5 mol %, the reaction proceeds at ambient temperature and reaction time is only 3 h. The product yields range from 20% to 99%. A reaction mechanism is also proposed, based on our experiment results.

SUBMITTER: Zhu Y

PROVIDER: S-EPMC6154665 | biostudies-literature | 2017 May

REPOSITORIES: biostudies-literature

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AlCl₃·6H₂O-Catalyzed Friedel-Crafts Alkylation of Indoles by the para-Quinone Methide Moiety of Celastrol.

Zhu Yi Y Chen Ziwen Z Huang Zhenfei Z Yan Siwei S Li Zhuoer Z Zhou Hu H Zhang Xiaokun X Su Ying Y Zeng Zhiping Z

Molecules (Basel, Switzerland) 20170516 5

A classical Friedel-Crafts alkylation of different indoles catalyzed by AlCl₃·6H₂O has been developed for a well-known important natural product, celastrol, resulting in a series of derivatives for further biological evaluation. The catalyst loading was reduced to 5 mol %, the reaction proceeds at ambient temperature and reaction time is only 3 h. The product yields range from 20% to 99%. A reaction mechanism is also proposed, based on our experiment results. ...[more]

PMID: 28509859

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