AlCl(3)·6H(2)O-Catalyzed Friedel-Crafts Alkylation of Indoles by the para-Quinone Methide Moiety of Celastrol

A classical Friedel-Crafts alkylation of different indoles catalyzed by AlCl(3)·6H(2)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...

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Detalles Bibliográficos
Autores principales: Zhu, Yi, Chen, Ziwen, Huang, Zhenfei, Yan, Siwei, Li, Zhuoer, Zhou, Hu, Zhang, Xiaokun, Su, Ying, Zeng, Zhiping
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2017
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6154665/
https://www.ncbi.nlm.nih.gov/pubmed/28509859
http://dx.doi.org/10.3390/molecules22050742
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author Zhu, Yi
Chen, Ziwen
Huang, Zhenfei
Yan, Siwei
Li, Zhuoer
Zhou, Hu
Zhang, Xiaokun
Su, Ying
Zeng, Zhiping
author_facet Zhu, Yi
Chen, Ziwen
Huang, Zhenfei
Yan, Siwei
Li, Zhuoer
Zhou, Hu
Zhang, Xiaokun
Su, Ying
Zeng, Zhiping
author_sort Zhu, Yi
collection PubMed
description A classical Friedel-Crafts alkylation of different indoles catalyzed by AlCl(3)·6H(2)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.
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spelling pubmed-61546652018-11-13 AlCl(3)·6H(2)O-Catalyzed Friedel-Crafts Alkylation of Indoles by the para-Quinone Methide Moiety of Celastrol Zhu, Yi Chen, Ziwen Huang, Zhenfei Yan, Siwei Li, Zhuoer Zhou, Hu Zhang, Xiaokun Su, Ying Zeng, Zhiping Molecules Article A classical Friedel-Crafts alkylation of different indoles catalyzed by AlCl(3)·6H(2)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. MDPI 2017-05-16 /pmc/articles/PMC6154665/ /pubmed/28509859 http://dx.doi.org/10.3390/molecules22050742 Text en © 2017 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Zhu, Yi
Chen, Ziwen
Huang, Zhenfei
Yan, Siwei
Li, Zhuoer
Zhou, Hu
Zhang, Xiaokun
Su, Ying
Zeng, Zhiping
AlCl(3)·6H(2)O-Catalyzed Friedel-Crafts Alkylation of Indoles by the para-Quinone Methide Moiety of Celastrol
title AlCl(3)·6H(2)O-Catalyzed Friedel-Crafts Alkylation of Indoles by the para-Quinone Methide Moiety of Celastrol
title_full AlCl(3)·6H(2)O-Catalyzed Friedel-Crafts Alkylation of Indoles by the para-Quinone Methide Moiety of Celastrol
title_fullStr AlCl(3)·6H(2)O-Catalyzed Friedel-Crafts Alkylation of Indoles by the para-Quinone Methide Moiety of Celastrol
title_full_unstemmed AlCl(3)·6H(2)O-Catalyzed Friedel-Crafts Alkylation of Indoles by the para-Quinone Methide Moiety of Celastrol
title_short AlCl(3)·6H(2)O-Catalyzed Friedel-Crafts Alkylation of Indoles by the para-Quinone Methide Moiety of Celastrol
title_sort alcl(3)·6h(2)o-catalyzed friedel-crafts alkylation of indoles by the para-quinone methide moiety of celastrol
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6154665/
https://www.ncbi.nlm.nih.gov/pubmed/28509859
http://dx.doi.org/10.3390/molecules22050742
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