Brønsted acidic ionic liquid-catalyzed tandem reaction: an efficient and sustainable approach towards the regioselective synthesis and molecular docking studies of 4-hydroxycoumarin-substituted indoles bearing lower E-factors

Satyajit Samanta; Rana Chatterjee; Subhankar Sarkar; Satyajit Pal; Anindita Mukherjee; Ilya I. Butorin; Olga A. Konovalova; Tathagata Choudhuri; Koushik Chakraborty; Sougata Santra; Grigory V. Zyryanov; Adinath Majee

doi:10.1039/D2OB01431A

Brønsted acidic ionic liquid-catalyzed tandem reaction: an efficient and sustainable approach towards the regioselective synthesis and molecular docking studies of 4-hydroxycoumarin-substituted indoles bearing lower E-factors†

Satyajit Samanta,

^a Rana Chatterjee,

^a Subhankar Sarkar,^a Satyajit Pal,^a Anindita Mukherjee,^b Ilya I. Butorin,^b Olga A. Konovalova,^b Tathagata Choudhuri,^c Koushik Chakraborty,^c Sougata Santra,

^b Grigory V. Zyryanov^bd and Adinath Majee

*^a

Author affiliations

* Corresponding authors

^a Department of Chemistry, Visva-Bharati (A Central University), Santiniketan 731235, India
E-mail: adinath.majee@visva-bharati.ac.in

^b Department of Organic and Biomolecular Chemistry, Chemical Engineering Institute, Ural Federal University, 19 Mira Street, Yekaterinburg, Russian Federation

^c Department of Biotechnology, Visva-Bharati (A Central University), Santiniketan 731235, India

^d I. Ya. Postovskiy Institute of Organic Synthesis, Ural Division of the Russian Academy of Sciences, 22 S. Kovalevskoy Street, 620219 Yekaterinburg, Russian Federation

Abstract

1-Butane sulfonic acid-3-methylimidazolium tosylate, [BSMIM]OTs, is a remarkable catalyst for the cascade synthesis of coumarin-functionalized indole derivatives via a tandem cyclization reaction of aniline and phenylglyoxal monohydrate. This reaction possibly proceeds through imine formation/nucleophilic addition/cyclization. In addition, this method shows lower E-factors. A clean reaction, easily accessible reactants, metal-free and environmentally friendly reaction conditions, and reusability of the catalyst are the notable advantages of this procedure. In addition, molecular docking studies show the theoretical possibility of binding these types of synthesized compounds to key proteins in tumorigenesis.

Organic & Biomolecular Chemistry

Brønsted acidic ionic liquid-catalyzed tandem reaction: an efficient and sustainable approach towards the regioselective synthesis and molecular docking studies of 4-hydroxycoumarin-substituted indoles bearing lower E-factors†

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Brønsted acidic ionic liquid-catalyzed tandem reaction: an efficient and sustainable approach towards the regioselective synthesis and molecular docking studies of 4-hydroxycoumarin-substituted indoles bearing lower E-factors

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