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Amine-functionalized graphene oxide nanosheets (AFGONs): an efficient bifunctional catalyst for selective formation of 1,4-dihydropyridines, acridinediones and polyhydroquinolines

  • Prasun Choudhury
  • Pranab Ghosh
  • Basudeb BasuEmail author
Short Communication
  • 33 Downloads

Abstract

We report here selective formation of functionalized 1,4-dihydropyridines (DHP), acridinediones and polyhydroquinolines in high yields using amine-functionalized graphene oxide nanosheets (AFGONs) as the bifunctional catalyst. The method overcomes the limitations of previous protocols affording a mixture of DHP and pyridine derivatives using graphene oxide as the catalyst. The mild reaction conditions are found compatible with a wide range of functional groups. It is presumed that a cooperative effect between the acidic and basic functionalities present in AFGONs may have exerted high catalytic efficiency as well as prevented further oxidation to pyridine derivatives. A plausible mechanism is proposed on the basis of some control experiments. The reactions can be scaled up conveniently, and the catalyst can be recycled for five consecutive runs without loss of its activity.

Graphical abstract

Keywords

Amine-functionalized graphene oxide Bifunctional catalyst 1,4-Dihydropyridine Hantzsch reaction Multi-component reaction (MCR) 

Notes

Acknowledgements

Financial support from Science and Engineering Research Board, New Delhi (Grant No EMR/2015/000549), is gratefully acknowledged. PC thanks UGC, New Delhi, for Senior Research Fellowship under UGC–NET. Authors express their sincere thanks to Dr. Sukanta Bhattacharyya, Supra Sciences Inc, San Francisco, CA, USA, for his keen interest in this work. The authors would like to acknowledge University Science and Instrumentation Centre for scanning electron microscopy (SEM) facility.

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflict of interest.

Supplementary material

11030_2019_9949_MOESM1_ESM.pdf (5.8 mb)
Supplementary material 1 (PDF 5653 kb)

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Authors and Affiliations

  1. 1.Department of ChemistryNorth Bengal UniversityDarjeelingIndia
  2. 2.Department of ChemistryRaiganj UniversityRaiganjIndia

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