&lt;strong&gt;Alkaline functionalized chitosan as highly efficient organocatalyst for the synthesis of 3-indole derivatives&lt;/strong&gt;

Mohammadghorban Dekamin,Zahra Alirezvani,ٍEhsan Valiey

doi:10.3390/ecsoc-21-04740

<strong>Alkaline functionalized chitosan as highly efficient organocatalyst for the synthesis of 3-indole derivatives</strong>

Mohammadghorban Dekamin, Zahra Alirezvani + Show 1 more

Open Access

https://doi.org/10.3390/ecsoc-21-04740

Copy DOI

Publication Date: Nov 3, 2017

License type: cc-by

Affiliation: Iran University of Science and Technology

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.  

Highlights

Multicomponent reactions (MCRs), have gained much attention in synthetic organic chemistry or significant advantages of atom economy, time-saving, inherent exploratory power and minimization of chemical waste
In continuation of our efforts in the synthesis and application of new heterogenous catalyst for organic transformations[3,4,5,6], we report our results for a facile and convenient synthesis of 3-indole derivatives using alkaline functionalized chitosan (1) as a highly efficient metal free organocatalyst
Synthesis of 3-indole derivatives catalyzed by alkaline functionalized chitosan (1)

Summary

Introduction

Multicomponent reactions (MCRs), have gained much attention in synthetic organic chemistry or significant advantages of atom economy, time-saving, inherent exploratory power and minimization of chemical waste. This strategy has proved to be a valuable and efficient methodology in the section of synthetic chemistry. A vast number of natural and synthetic indole derivatives have been found a respected value in pharmaceutical and medical applications since they are able to bind with high affinity to many receptors.

Results

Conclusion