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L-Proline catalyzed one-pot three-component synthesis and evaluation for biological activities of tetrahydrobenzo[b]pyran: evaluation by green chemistry metrics

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Abstract

A series of tetrahydrobenzo[b]pyrans derivatives were synthesized with substituted pyrazole carbaldehydes, malononitrile and dimedone by ecofriendly L-proline catalyst in aqueous ethanol. The synthesized compounds were characterized using FTIR, 1H NMR, 13C NMR and Mass spectral techniques. This method holds the advantages of one-pot multicomponent, simple synthetic route, mild reaction conditions, high yield, use of less toxic chemicals and use of eco-friendly catalyst. We also report the study of the synthetic protocol by green chemistry metrics indicates a green relevance. Also, synthesized compounds were screened for their anti-inflammatory and antioxidant activity. Most of the tetrahydrobenzo[b]pyrans derivatives exhibit excellent activity.

Graphical abstract

A series of tetrahydrobenzo[b]pyrans derivatives were synthesized with substituted pyrazole carbaldehydes, malononitrile and dimedone using eco-friendly L-proline as a catalyst in aqueous ethanol. We also report the examination of the synthetic protocol by green chemistry metrics suggests that synthetic protocol has green relevance. Anti-inflammatory activity and antioxidant activity for tetrahydrobenzo[b]pyran derivatives are performed. Some of the synthesized compounds showed excellent anti-inflammatory as well as antioxidant activity.

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Acknowledgements

Author(s) are thankful to the Principal of Karmaveer Bhaurao Patil Mahavidyalaya, Pandharpur, Shri. Shivaji Mahavidyalaya, Barshi and The Poona Gujarati Kelwani Mandal’s Haribhai V. Desai College, Pune (Dr. Ganesh Raut) for providing essential facilities. Author (s) are also thankful to the Department of instrumentation Punyashlok Ahilyadevi Holkar Solapur University, Solapur for providing spectral characterization.

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Authors and Affiliations

  1. Chemistry Research Laboratory, Shri Shivaji Mahavidyalaya, Barshi, Maharashtra, 413401, India

    PRADEEP KATE

  2. Department of Chemistry, Haribhai V. Desai College, Pune, Maharashtra, 411002, India

    VIKRAM PANDIT

  3. RKM College, Akurdi, Pune, Maharashtra, 411035, India

    VIVEKANAND JAWALE

  4. Department of Chemistry, Sangola College, Sangola, Maharashtra, 413307, India

    MADHUSUDAN BACHUTE

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  1. PRADEEP KATE
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Correspondence to MADHUSUDAN BACHUTE.

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KATE, P., PANDIT, V., JAWALE, V. et al. L-Proline catalyzed one-pot three-component synthesis and evaluation for biological activities of tetrahydrobenzo[b]pyran: evaluation by green chemistry metrics. J Chem Sci 134, 4 (2022). https://doi.org/10.1007/s12039-021-01990-7

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  • DOI: https://doi.org/10.1007/s12039-021-01990-7

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