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Alkaline functionalized chitosan as highly efficient organocatalyst for the synthesis of 3-indole derivatives
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1  Pharmaceutical and Biologically-Active Compounds Research Laboratory, Department of Chemistry, Iran University of Science and Technology, Tehran 16846-13114, Iran


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.



(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