EventsThe 21st International Electronic Conference on Synthetic Organic Chemistry
Event submissions
Published
with-doi10.3390/ecsoc-21-04740
This submission belongs to the session A. General Organic Synthesis of the event The 21st International Electronic Conference on Synthetic Organic Chemistry
Published date
03 Nov, 2017
Citation
Zahra Alirezvani, Mohammadghorban Dekamin, ٍEhsan Valiey, Alkaline functionalized chitosan as highly efficient organocatalyst for the synthesis of 3-indole derivatives, in Proceedings of The 21st International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2017, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-21-04740
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Alkaline functionalized chitosan as highly efficient organocatalyst for the synthesis of 3-indole derivatives

ٍEhsan Valiey 1
Mohammadghorban Dekamin 1
Zahra Alirezvani 1
1. Pharmaceutical and Biologically-Active Compounds Research Laboratory, Department of Chemistry, Iran University of Science and Technology, Tehran 16846-13114, Iran
Abstract

Indole frameworks have been extensively known as vital moieties in biological, agrochemical and pharmacological compounds.1 Several MCR methods have been reported for the synthesis of substituted indoles. Within indole derivatives, 3-substituted indoles are versatile intermediates for the synthesis of a widespread range of indole compounds. The conjugate addition of indoles to Michael acceptors affords easy access to 3-substituted indole derivatives. 2

In continuing to our ongoing efforts towards developing efficient catalysts for different MCRs3,4, we report herein a general route to 3-substituted indole derivatives via the three-component reaction of indoles, malononitrile and aldehydes promoted by a new alkaline functionalized chitosan, as a highly efficient and recoverable catalyst (Scheme 1).

 

­ Scheme 1. The three-component reaction of aldehydes, indole and malononitrile.

 

References

(1) Shiri, M. Chemical reviews 2012, 112, 3508.

(2) Qu, Y.; Ke, F.; Zhou, L.; Li, Z.; Xiang, H.; Wu, D.; Zhou, X. Chemical Communications 2011, 47, 3912.

(3) Dekamin, M. G.; Azimoshan, M.; Ramezani, L. Green Chemistry 2013, 15, 811.

(4) Dekamin, M. G.; Kazemi, E.; Karimi, Z.; Mohammadalipoor, M.; Naimi-Jamal, M. R. International journal of biological macromolecules 2016, 93, 767.

 

Keywords
indole
chitosan
recoverable catalyst
Michael acceptors
Manuscript
Valiey-Full paper ECSOC-21 (24-10-2017).pdf
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