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Synthesis and characterization of guanine-functionalized mesoporous silica [SBA-16-G]: a metal-free and recyclable heterogeneous solid base catalyst for synthesis of pyran-annulated heterocyclic compounds

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Abstract

The synthesis of a new solid base catalyst, i.e., guanine-functionalized mesoporous silica [SBA-16-G], is described. The synthesized catalyst has been fully characterized by FTIR, solid state 13C NMR, TGA, XRD, BET, FESEM, EDAX, CHNS elemental analysis, CO2-TPD, and TEM techniques. The surface area and the basicity of the synthesised [SBA-16-G] were found to be 524 m2/g and 3.230 mmol/g, respectively, based on BET and CO2-TPD analysis. The catalytic activity of the synthesized catalyst has been explored in the synthesis of a series of biologically and pharmaceutically active pyran-annulated heterocyclic compounds from a one-pot three-component reaction of an aromatic aldehyde, malononitrile/ethyl cyanoacetate, and a C–H activated acidic compound, in the presence of a catalytic amount (10 wt%) of [SBA-16-G]. The catalyst is metal-free, easy to synthesize and to isolate from the reaction mixture, and recycled up to four times without significant loss of catalytic activity.

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Acknowledgements

RG and SL acknowledge the Director, IIT (ISM), Dhanbad, for awarding research fellowships. The authors would like to thank CRF at IIT (ISM), Dhanbad, for the FESEM images. We are grateful to Vijay Gupta, SRF, Department of Chemistry, IISER Mohali, Punjab, India, for recording the 1H and 13C NMR data.

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  1. Department of Applied Chemistry, Indian Institute of Technology (Indian School of Mines), Dhanbad, Jharkhand, 826004, India

    Radha Gupta, Samaresh Layek & Devendra Deo Pathak

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  1. Radha Gupta
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Correspondence to Devendra Deo Pathak.

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Gupta, R., Layek, S. & Pathak, D.D. Synthesis and characterization of guanine-functionalized mesoporous silica [SBA-16-G]: a metal-free and recyclable heterogeneous solid base catalyst for synthesis of pyran-annulated heterocyclic compounds. Res Chem Intermed 45, 1619–1637 (2019). https://doi.org/10.1007/s11164-018-3693-5

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