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Green synthesis of quinolines via A3-coupling by using graphene oxide-supported Brønsted acidic ionic liquid

Abstract

Graphene oxide-supported Bronsted acidic ionic liquid ([GrBenzImi]SO3H) has been prepared by covalent grafting of benzimidazole unit in the matrix of graphene oxide followed by reaction with 1,4-butane sultone and hydrochloric acid. [GrBenzImi]SO3H has been characterized by various techniques including Fourier transform infrared spectroscopy (FTIR), FT-Raman (FT-Raman spectroscopy), CP-MAS 13C NMR spectroscopy, thermogravimetric analysis, energy-dispersive X-ray analysis, Brunauer–Emmett–Teller surface area, X-ray diffraction, and transmission electron microscopy. [GrBenzImi]SO3H was successfully employed as heterogeneous catalyst in A3-coupling reaction of aryl aldehydes, anilines and phenylacetylene for the synthesis of 2,4-disubstituted quinolines using water/ethanol system (1:1) as green medium. [GrBenzImi]SO3H could be recycled six times without significant loss in the yield of product.

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Acknowledgements

We gratefully acknowledge Indian Institute of Bombay (IITB), North-Eastern Hill University Shillong (NEHU), Indian Institute of Technology, Madras (IITM) for providing spectral facilities and Shivaji University Kolhapur for providing financial assistance and Golden Jubilee Research Fellowship (GJRF).

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Correspondence to Gajanan Rashinkar.

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Gajare, S., Patil, A., Hangirgekar, S. et al. Green synthesis of quinolines via A3-coupling by using graphene oxide-supported Brønsted acidic ionic liquid. Res Chem Intermed (2020). https://doi.org/10.1007/s11164-020-04099-7

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Keywords

  • Bronsted acidic ionic liquid
  • Graphene oxide
  • A3-coupling
  • 2,4-disubstituted quinolines
  • Reusability