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Microwave-induced CAN promoted atom-economic synthesis of 1H-benzo[b]xanthene and 4H-benzo[g]chromene derivatives of N-allyl quinolone and their antimicrobial activity

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Abstract

Some new 1H-benzo[b]xanthene and 4H-benzo[g]chromene derivatives of N-allyl quinolone were efficiently synthesized via microwave-induced one-pot three component reaction of N-allyl quinolones, 2-hydroxy-1,4-naphthoquinone and cyclic β-diketones/malononitrile, and iso-propylcyanoacetate in the presence of catalytic amount of ceric ammonium nitrate under solvent-free condition. This methodology allowed us to achieve the desired products in excellent yields in a very short time without the use of solvent. The % atom economy was calculated for all the newly synthesized compounds and found in the range of 92–96 %. Titled derivatives were elucidated by 1H NMR, 13C NMR, FT-IR, elemental analysis, and mass spectral data as well as tested against a panel of pathogenic strains of bacteria and fungi using by microdilution minimum inhibitory concentration method. The structural activity relationship analysis demonstrated that electronic influence and lipophilicity of different groups make much difference in the antimicrobial potency.

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Acknowledgments

The authors are thankful to the Head, Department of Chemistry, Sardar Patel University, for providing 1H NMR and 13C NMR spectroscopy and research facilities. We are also thankful to the Oxygen Healthcare Research Pvt. Ltd., Ahmedabad, for providing mass spectroscopy facilities, Vaibhav Laboratories, Ahmedabad, Gujarat, India, for the FT-IR; SICART, Vallabh Vidyanagar, for elemental analysis, and Dhanji P. Rajani, Microcare Laboratory, Surat, Gujarat, India for antimicrobial screening of the compounds reported herein.

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  1. Department of Chemistry, Sardar Patel University, Vallabh Vidyanagar, 388120, Gujarat, India

    Hardik H. Jardosh & Manish P. Patel

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  1. Hardik H. Jardosh
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  2. Manish P. Patel
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Correspondence to Manish P. Patel.

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Jardosh, H.H., Patel, M.P. Microwave-induced CAN promoted atom-economic synthesis of 1H-benzo[b]xanthene and 4H-benzo[g]chromene derivatives of N-allyl quinolone and their antimicrobial activity. Med Chem Res 22, 2954–2963 (2013). https://doi.org/10.1007/s00044-012-0301-x

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