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Novel task-specific ionic liquid [Et2NH(CH2)2CO2H][AcO] as a robust catalyst for the efficient synthesis of some pyran-annulated scaffolds under solvent-free conditions

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Abstract

A novel task-specific ionic liquid, 2-carboxy-N,N-diethylethanaminium acetate denoted as [Et2NH(CH2)2CO2H][AcO], is prepared in an easy process and fully characterized by using suitable methods such as FT-IR, 1H-NMR, 13C-NMR, and TG, DTG and DTA analyses. After preparation, the promoting ability of this catalyst for one-pot multicomponent synthesis of 2-amino-4H-chromenes, dihydropyrano[3,2-c]chromenes and dihydropyrano[2,3-c]pyrazoles using in situ-developed arylidenemalononitriles through Knoevenagel reaction under solvent-free conditions is described. The sustainable procedure, short reaction times (6–36 min), effortless work-up, non-chromatographic purification, good-to-excellent product yields (79–96%), ease of recovery and reusability of the catalyst up to six reaction runs without a decrease of activity are the notable features of the present protocol.

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Acknowledgements

The authors are grateful to the management of Dr. Rafiq Zakaria campus, Aurangabad, for providing the laboratory facilities. We are also thankful to the SAIF Panjab University, Chandigarh and STIC Cochin University of Science & Technology, Cochin for spectral analysis.

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Authors and Affiliations

  1. Post Graduate and Research Centre, Maulana Azad College, Aurangabad, Maharashtra, 431001, India

    Mohd Akmal Shaikh

  2. Dr. Rafiq Zakaria College for Women, Aurangabad, Maharashtra, 431001, India

    Mohd Akmal Shaikh & Mazahar Farooqui

  3. Government College of Arts and Science, Aurangabad, Maharashtra, 431001, India

    Syed Abed

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  1. Mohd Akmal Shaikh
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  2. Mazahar Farooqui
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Shaikh, M.A., Farooqui, M. & Abed, S. Novel task-specific ionic liquid [Et2NH(CH2)2CO2H][AcO] as a robust catalyst for the efficient synthesis of some pyran-annulated scaffolds under solvent-free conditions. Res Chem Intermed 45, 1595–1617 (2019). https://doi.org/10.1007/s11164-018-3696-2

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  • DOI: https://doi.org/10.1007/s11164-018-3696-2

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