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Current Organocatalysis

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ISSN (Print): 2213-3372
ISSN (Online): 2213-3380

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Research Article

Multicomponent Synthesis of Structurally Diverse Spiroheterocycles using Bio-organic Catalyst in Aqueous Medium

Author(s): Asha Verma, Gargi Pathak, Sandeep Kumar, Vineeta Khatri*, Rajni Johar Chhatwal and Dinesh Kumar Arya*

Volume 11, Issue 4, 2024

Published on: 31 January, 2024

Page: [321 - 329] Pages: 9

DOI: 10.2174/0122133372287369240124062533

Price: $65

Abstract

Background: MCRs are one of the most significant tools in the synthesis of organic compounds. MCR is a rapid chemical technique that uses three or more reactants to produce products that sustain all structural and substructural properties of the initial components. MCRs are useful in all fields of synthetic chemistry because of their rapid rate of reaction, simple procedure and excellent yields. We reported an efficient and environmentally friendly domino approach for the synthesis of spiroheterocycles spiro annulated with indeno[1,2-b]quinoline.

Method: The spiroheterocycles with privileged heterocyclic substructures have been synthesized using taurine (2-aminoethanesulfonic acid) as a green, sustainable, bio-organic and recyclable catalyst in a three-component reaction of isatins, 1,3-diketones, and 1-napthylamine in aqueous media. The present synthetic method is probably the first report to synthesize spiroheterocycles, spiroannulated with indeno[1,2-b]quinoline. Furthermore, the approach is valuable because of the excellent yield that results from the reaction in 15-20 min.

Result: The optimization of reaction conditions is an important case of efficient synthesis. The solvent, temperature, time and catalyst loading were all examined. The reusability of the catalyst was also investigated experimentally. The used catalyst taurine has a high activity as well as good reusability. The present synthetic protocol will be extended to synthesise a library of hybrid compounds. The present synthetic approach is cost-effective, and time-efficient with an easy-workup methodology that gives outstanding yields (80–95%) in 15–20 min.

Conclusion: Taurine-catalyzed multicomponent reaction is a novel and efficient method for the synthesis of spiroannulated indeno[1,2-b]quinolines. The high catalytic activity of taurine as a catalyst with water as a green solvent makes the process environmentally friendly. The special features of the synthetic protocol include synthetic efficiency, operational simplicity, and reusability of the catalyst and it is expected to make significant contributions not only to drug discovery studies but also to pharmaceutical and therapeutic chemistry in view of introducing molecular diversity in the synthesized molecules.

Keywords: Multicomponent reactions, environmentally friendly, green and sustainable bio-organic catalyst, taurine (2-aminoethanesulfonic acid), spiroheterocycles, indenoquinolines, NK-1 receptor.

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