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Montmorillonite K10 clay promoted one-pot pseudo-five-component synthesis of 5-cyano-6-(phenylthio)-2-((1-phenylvinyl)imino)-4- aryl(or heteroaryl)-2H-pyran-3-carboxylic acid derivatives and their potential cytotoxic activity

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Abstract

A facile green accessibility for the synthesis of novel, distinctly substituted 2H-pyran analogues employing montmorillonite K10 clay as a sustainable catalyst via a one-pot multi-component reaction involving various aldehydes, thiophenol and cyanoacetic acid with acetophenone has been developed. The noteworthy features of the current methodology are short reaction time (1.5-2 h), good yields (70-82%), convenient technique, operational simplicity, ease of work-up, and reusability of the catalyst up to two runs, adhering to green chemistry principles. A spectroscopic assessment validated the structure of all the synthesized products. This multi-component one-pot transformation conveniently forms two new C-C bonds, one C-O bond, one C-S bond, and two new rings with all reactants consumed efficiently. Additionally, all synthesized compounds have been evaluated for anti-cancer activity, and two of them were found to be efficacious against human breast cancer cell line, namely, MDA-MB 231.

Graphical Abstract

A green and efficient method has been developed for synthesizing novel 2H-pyran analogues using montmorillonite K10 clay as a catalyst. The method involves a one-pot multi-component reaction and yields high products (70–82%) while adhering to green chemistry principles. The synthesized compounds have shown efficacy against human breast cancer cell line MDA-MB 231.

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Acknowledgments

The researchers are highly gratified with the infrastructural and financial help under the CURIE program from the WISE-KIRAN division of the Department of Science and Technology, New Delhi, India to IIS (deemed to be University), Jaipur, India (File No. DST/CURIE-02/2023/IISU) and to the MRC, MNIT (Jaipur, India) for providing the NMR instrumentation facilities.

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Authors and Affiliations

  1. Department of Chemistry, The IIS (Deemed to be University), Jaipur, 302020, India

    Pragati Sharma & Pragya Sinha

  2. Department of Biotechnology, The IIS (Deemed to be University), Jaipur, 302020, India

    Nidhi Gupta

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  1. Pragati Sharma
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Correspondence to Pragya Sinha.

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Sharma, P., Sinha, P. & Gupta, N. Montmorillonite K10 clay promoted one-pot pseudo-five-component synthesis of 5-cyano-6-(phenylthio)-2-((1-phenylvinyl)imino)-4- aryl(or heteroaryl)-2H-pyran-3-carboxylic acid derivatives and their potential cytotoxic activity. J Chem Sci 136, 15 (2024). https://doi.org/10.1007/s12039-023-02247-1

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