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Cinchonine-driven multi-component domino Knoevenagel–Michael strategy: metal-free synthesis of quinoline-based 4H-pyran and tetrahydro-4H-chromene derivatives

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Abstract

Cinchonine-catalyzed simple, expeditious, and efficient protocol for the synthesis of quinoline-based 4H-pyran and tetrahydro-4H-chromenes has been demonstrated via one-pot domino Knoevenagel–Michael cyclocondensation reaction of aromatic aldehyde, active methylene compound and activated C–H acids like alkylacetoacetates/dimedone in ethanol under reflux. This protocol enables a rapid construction of diverse range of 4H-pyran and tetrahydro-4H-chromene derivatives from readily available starting materials. Short reaction time, mild reaction conditions, broad substrate scope, high yields, metal-free approach, and purification without column chromatography are notable features of this methodology.

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Acknowledgements

P.K. thanks the University Grants Commission for a BSR fellowship. The contribution of IIM Jammu and the Department of Chemistry at University of Jammu for providing spectral data is also acknowledged.

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  1. Synthetic Organic Chemistry Laboratory, Faculty of Sciences, Shri Mata Vaishno Devi University, Katra, J & K, 182 320, India

    Parteek Kour & Anil Kumar

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  1. Parteek Kour
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  2. Anil Kumar
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Kour, P., Kumar, A. Cinchonine-driven multi-component domino Knoevenagel–Michael strategy: metal-free synthesis of quinoline-based 4H-pyran and tetrahydro-4H-chromene derivatives. Res Chem Intermed 46, 2025–2034 (2020). https://doi.org/10.1007/s11164-020-04097-9

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