Catalyst-free green synthesis of dihydropyrano[2,3-c]pyrazole scaffolds assisted by ethylene glycol (E-G) as a reusable and biodegradable solvent medium

Abstract

We revealed a catalyst-free, green and rapid one-pot four-component tandem strategy for the preparation of dihydropyrano[2,3-c]pyrazoles – a biologically significant scaffold – via Knoevenagel-Michael cyclocondensation based on green chemistry principles. Highlights of the current practice are the application of non-hazardous reaction circumstances, catalyst-free, operational simplicity, use of inexpensive initiating substances, isolation of pure product via easy filtration thus preventing the requirement for column chromatography, metal-free, excellent yields, time-saving aspects of the reaction. However, the green ethylene glycol (E-G) can be recycled at least six times with no considerable reduction in activity making it greatly advantageous in addressing the industrial requirements and environmental worries.

Graphic Abstract

The catalyst-free and environmentally friendly synthesis of dihydropyrano[2,3-c]pyrazole scaffolds are reported via ethylene glycol (E-G) as a green, reusable and biodegradable promoting media via tandem Knoevenagel-Michael cyclocondensation reaction of ethyl acetoacetate, hydrazine hydrate/phenylhydrazine, aromatic/aliphatic aldehydes and malononitrile provided the anticipated products in outstanding yields and short reaction times which might solve some cost problems in industry

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Acknowledgements

We gratefully acknowledge the financial support from the Research Council of the Apadana Institute of Higher Education.

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Correspondence to Farzaneh Mohamadpour.

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Mohamadpour, F. Catalyst-free green synthesis of dihydropyrano[2,3-c]pyrazole scaffolds assisted by ethylene glycol (E-G) as a reusable and biodegradable solvent medium. J Chem Sci 132, 72 (2020). https://doi.org/10.1007/s12039-020-01775-4

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Keywords

  • Catalyst-free
  • ethylene glycol (E-G)
  • green protocol
  • reusable solvent medium
  • dihydropyrano[2,3-c]pyrazoles