Exploring the synthetic potential of a g-C3N4·SO3H ionic liquid catalyst for one-pot synthesis of 1,1-dihomoarylmethane scaffolds via Knoevenagel–Michael reaction

Soni, Shivani; Teli, Pankaj; Sahiba, Nusrat; Teli, Sunita; Agarwal, Shikha

doi:10.1039/d3ra01971c

RSC Adv.

2023

DOI: 10.1039/d3ra01971c

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Exploring the synthetic potential of a g-C₃N₄·SO₃H ionic liquid catalyst for one-pot synthesis of 1,1-dihomoarylmethane scaffolds via Knoevenagel–Michael reaction

Shivani Soni¹,

Pankaj Teli²,

Nusrat Sahiba³

et al.

Abstract: Functionalized 1,1-dihomoarylmethane scaffolds (bis-cyclohexanediones, bis-pyrazoles, and bis-coumarins) have been synthesized using g-C3N4·SO3H ionic liquid catalyst via Koevenagel–Michale reaction with high yields and short time.

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Cited by 5 publications

References 73 publications

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Unsymmetrical Bis‐Coumarin Based on o‐Hydroxy Aldehydes and 4‐Hydroxy Coumarin: Expedient Synthesis, Single Crystal X‐rays and DFT Studies

Das,

Paul,

et al. 2023

ChemistrySelect

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Bis‐coumarins are distinguished derivatives of coumarin which bear numerous pharmaceutical and other applications. In continuation of our ongoing research towards the development of benign protocols for various heterocyclic systems, herein we report an Amberlyst 15 mediated synthesis of unsymmetrical bis‐coumarins via in situ generation and cyclization of symmetrical bis‐coumarinyl methanes derived from o‐hydroxy aromatic aldehydes and 4‐hydroxy coumarin. Aldehydes of both electron‐donating and electron‐withdrawing units underwent smooth conversion to their respective unsymmetrical bis‐coumarins (76–98 % yield) without leaving any side products or intermediates. The catalyst used in the present protocol is cost‐effective, eco‐friendly, and readily available which could be recovered and reused several times. This methodology offers operational simplicity, low catalyst loading, and avoids the use of toxic solvents/reagents and the product can be isolated without chromatography. DFT study indicated that the driving force for the cyclisation of symmetrical bis‐coumarin is the minimization of the tetrahedral bond angle deviations along with other small non‐covalent interactions. Some DFT data was also verified with the data obtained from the X‐rays crystallographic study.

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Unsymmetrical Bis‐Coumarin Based on o‐Hydroxy Aldehydes and 4‐Hydroxy Coumarin: Expedient Synthesis, Single Crystal X‐rays and DFT Studies

Das,

Paul,

et al. 2023

ChemistrySelect

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show abstract

L-proline-Brønsted acid deep eutectic mixture (DEM) triggered consecutive Claisen–Schmidt and Michael addition reactions

Chaudhary,

Patel,

Gupta

et al. 2024

Res Chem Intermed

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Empowering sustainability: Charting the seven years of progress in g-C₃N₄ based materials and their crucial role in building a greener future

Soni,

Teli,

Teli

et al. 2024

Sustainable Chemistry and Pharmacy

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Exploring the synthetic potential of a g-C₃N₄·SO₃H ionic liquid catalyst for one-pot synthesis of 1,1-dihomoarylmethane scaffolds via Knoevenagel–Michael reaction

Abstract: Functionalized 1,1-dihomoarylmethane scaffolds (bis-cyclohexanediones, bis-pyrazoles, and bis-coumarins) have been synthesized using g-C3N4·SO3H ionic liquid catalyst via Koevenagel–Michale reaction with high yields and short time.

Cited by 5 publications

References 73 publications

Unsymmetrical Bis‐Coumarin Based on o‐Hydroxy Aldehydes and 4‐Hydroxy Coumarin: Expedient Synthesis, Single Crystal X‐rays and DFT Studies

Unsymmetrical Bis‐Coumarin Based on o‐Hydroxy Aldehydes and 4‐Hydroxy Coumarin: Expedient Synthesis, Single Crystal X‐rays and DFT Studies

L-proline-Brønsted acid deep eutectic mixture (DEM) triggered consecutive Claisen–Schmidt and Michael addition reactions

Empowering sustainability: Charting the seven years of progress in g-C₃N₄ based materials and their crucial role in building a greener future

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