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Highly efficient and diversity-oriented solvent-free synthesis of biologically active fused heterocycles using glycerol-based sulfonic acid

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Abstract

The present article involves preparation of some novel fused quinazoline analogs by employing aromatic aldehydes, 1,3-cyclic diketones (dimedone/cyclohexanedione) and urea/2-aminobenzothiazole, in catalytic amount of glycerol-based sulfonic acid. By employing glycerol-based sulfonic acid as a catalyst, the threat of metal contamination has been eradicated. The putative mechanism of this MCR strategy is similar to the Biginelli reaction involving Knoevenagel condensation followed by Michael addition. A series of fused derivatives confirmed the high functional group tolerance of the present protocol. The fabricated pathway has numerous advantages like high yields of desired products, green, solvent-free, and use of easily recoverable and reusable heterogeneous catalyst. Further, the anti-microbial results confirmed that among the synthesized compounds, compounds 4c and 6a were found more active as compared to ciprofloxacin against tested bacterial strains. Compounds 4g and 6a were found more active against tested fungal strains as compared to fluconazole.

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Acknowledgements

The authors are thankful to Head, Department of Chemistry for providing necessary laboratory facilities. The authors would also like to acknowledge Sophisticated Analytical Instrumentation Facility, Chandigarh for spectral characterization, India. A. Sethiya is thankful to UGC-MANF for providing Senior Research Fellowship to carry out this work. Nusrat Sahiba and Pankaj Teli are thankful to CSIR for Senior Research Fellowship.

Funding

This work was supported by the UGC-MANF (201819-MANF-2018-19-RAJ-91971).

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Authors and Affiliations

  1. Synthetic Organic Chemistry Laboratory, Department of Chemistry, MLSU, Udaipur, Udaipur, Rajasthan, 313001, India

    Ayushi Sethiya, Priyanka Kalal, Pankaj Teli, Nusrat Sahiba, Jay Soni & Shikha Agarwal

  2. Department of Chemistry, Sheth M.N. Science College, Patan, Gujarat, India

    Deepkumar Joshi

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  1. Ayushi Sethiya
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  2. Priyanka Kalal
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Correspondence to Shikha Agarwal.

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Full experimental details and copies of 1H NMR and 13C NMR spectra of all the synthesized compounds associated with the article have been provided in supporting information (DOCX 6587 KB)

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Sethiya, A., Kalal, P., Teli, P. et al. Highly efficient and diversity-oriented solvent-free synthesis of biologically active fused heterocycles using glycerol-based sulfonic acid. Res Chem Intermed 48, 4711–4727 (2022). https://doi.org/10.1007/s11164-022-04822-6

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