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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

A Facile Synthesis of Tris(indolyl)propanes by Concerted 1,2- and 1,4-Friedel-Crafts Attack of Indoles to α,β-Unsaturated Aldimines

Manping Zhao A , Xiuli Zhang B , Chengxiang He A , Pinaki S. Bhadury C and Zhihua Sun A D
+ Author Affiliations
- Author Affiliations

A College of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, Shanghai, 201620, China.

B School of Fundamental Studies, Shanghai University of Engineering Science, Shanghai, 201620, China.

C Northernchem Inc., Thorold Stone Road; Niagara Falls, Ontario L2J 1A1, Canada.

D Corresponding author. Email: sungaris@gmail.com

Australian Journal of Chemistry 68(2) 327-334 https://doi.org/10.1071/CH14156
Submitted: 18 March 2014  Accepted: 9 May 2014   Published: 5 August 2014

Abstract

The Friedel-Crafts reaction of indoles with a wide range of α,β-unsaturated aldimines catalysed by binaphthyl phosphoric acid is demonstrated. The resulting tris(indolyl)propanes are presumably generated by a concerted 1,2- and 1,4-nucleophilic attack to the conjugated imines. According to the preliminary bioassay results, the compound 4e exhibits moderate activity against pancreatic cancer cells.


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