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Sodium acetate/MWI: a green protocol for the synthesis of tetrahydrobenzo[α]xanthen-11-ones with biological screening

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Abstract

An efficient, straightforward and rapid method has been developed for the synthesis of tetrahydrobenzo[α] xanthen-11-one using sodium acetate. The reaction was performed via three components: β-naphthol, dimedone with various aromatic aldehydes under solvent-free microwave irradiation and conventional heating condition. We observed an efficient result for microwave synthesis than conventional heating. The synthesized tetrahydrobenzo[α]xanthen-11-one (4a–l) was screened for their antimicrobial activity against two bacteria (Escherichia coli and Bacillus subtilis) and two fungal strains (Aspergillus niger and Saccharomyces cerevisiae). The synthesized products: 9, 10-dihydro-9, 9-dimethyl-12-(4-nitrophenyl)-8H-benzo[a]xanthen-11(12H)-one, 9, 10-dihydro-9, 9-dimethyl-12-(2, 4-dichlorophenyl)-8H-benzo[a]xanthen-11(12H)-one, 9, 10-dihydro-9, 9-dimethyl-12-(6-methyl-4-oxo-4H-chromen-3-yl)-8H-benzo[a]xanthen-11(12H)-one exhibit good antimicrobial activity. The developed protocol is graced with appealing advantages such as high purity, simple operation, excellent yields, inexpensive and easy availability of catalyst.

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Acknowledgements

Authors are thankful to Department of Chemistry, Yashavantrao Chavan Institute of Science, Satara, for providing laboratory facilities and also thankful to DBT-STAR Scheme, Research Advisory Committee for giving seed money.

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Authors and Affiliations

  1. Department of Chemistry, Yashavantrao Chavan Institute of Science, Satara, Maharashtra, 415001, India

    Prasad Mane, Bipin Shinde, Vilas Gawade & Arvind Burungale

  2. Department of Biotechnology, Yashavantrao Chavan Institute of Science, Satara, Maharashtra, 415001, India

    Pankaj Mundada

  3. Department of Chemistry, S.M. Joshi College, Hadapsar, Pune, Maharashtra, 411028, India

    Arvind Burungale

  4. Chhatrapati Shivaji College, Satara, Maharashtra, 415001, India

    Bhausaheb Karale

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  1. Prasad Mane
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  2. Bipin Shinde
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Correspondence to Arvind Burungale.

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Mane, P., Shinde, B., Mundada, P. et al. Sodium acetate/MWI: a green protocol for the synthesis of tetrahydrobenzo[α]xanthen-11-ones with biological screening. Res Chem Intermed 46, 231–241 (2020). https://doi.org/10.1007/s11164-019-03945-7

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