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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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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) doi:10.1007/s11164-019-03945-7

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Keywords

  • Antimicrobial screening
  • Microwave irradiation
  • Solvent-free condition
  • Tetrahydrobenzo[α] xanthen-11-one