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[BBSA-DBN][HSO4]: a novel –SO3H functionalized Bronsted acidic ionic liquid for easy access of quinoxalines

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Abstract

A novel –SO3H difunctionalized Bronsted acidic ionic liquid (BAIL) 1, 5-bis (butanesulphonic acid)-diazobicyclo [4,3,0] non-5-enium hydrogen sulphate [BBSA-DBN][HSO4] is introduced for efficient synthesis of quinoxalines via condensation of substituted 1,2-diketones and various aromatic 1,2-diamines. It could serve as a dual functional catalyst for these reactions. This method has the advantages of mild reaction conditions, high yields, short reaction times, easy work-up, non-chromatographic separations and being environmentally friendly. This protocol provides an effective and environmentally friendly alternative methodology for production of quinoxalines and extends the chemical utilization of benzil in organic synthesis. This room-temperature-derived ionic liquid is highly acidic due to presence of two –SO3H groups and two HSO4− anions. Moreover, the IL [BBSA-DBN][HSO4] could be easily recovered and reused at least five times without change in its catalytic activity. The formation of IL [BBSA-DBN][HSO4] was confirmed by 1H, 13C NMR spectroscopic techniques.

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Acknowledgements

The author MUP wish to acknowledge Shivaji University Kolhapur for providing financial assistance under Research Initiation Scheme [SU/C&U.D. Section/36/183, dated 05 May 2018] and author SKS thankful to Council of Scientific & Industrial Research (CSIR), New Delhi for the award of Senior Research Fellowship (SRF).

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Authors and Affiliations

  1. Synthetic Research Laboratory, PG Department of Chemistry, PDVP College (Affiliated to Shivaji University Kolhapur), Tasgaon, Sangli, MS, 416 312, India

    Megha U. Patil, Sachinkumar K. Shinde, Sandip P. Patil & Suresh S. Patil

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  1. Megha U. Patil
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  2. Sachinkumar K. Shinde
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  3. Sandip P. Patil
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  4. Suresh S. Patil
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Correspondence to Suresh S. Patil.

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Patil, M.U., Shinde, S.K., Patil, S.P. et al. [BBSA-DBN][HSO4]: a novel –SO3H functionalized Bronsted acidic ionic liquid for easy access of quinoxalines. Res Chem Intermed 46, 4923–4938 (2020). https://doi.org/10.1007/s11164-020-04227-3

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