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Synthesis of sulfonated carbon-based solid acid as a novel and efficient nanocatalyst for the preparation of highly functionalized piperidines and acylals: a DFT study

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Abstract

A novel carbon-based solid-acid nanocatalyst (Sta-SO3H) was simply prepared for the first time by the thermal treatment of sulfuric acid with starch at 180 °C in a sealed autoclave. The catalytic activities of Sta-SO3H as an efficient and reusable catalyst were investigated by the condensation reaction of aldehyde, amine and β-keto ester for the synthesis of functionalized piperidines under solvent-free conditions at room temperature in good to high yields. Density functional theory calculations were used to study the structure of methyl 1,2,6-triphenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate (MPPC) as well as the thermochemistry of the multicomponent reaction. The theoretically calculated infrared and 1H nuclear magnetic resonance spectra of MPPC were compared to the experimental data. It was found that the synthesis of MPPC is exothermic accompanied by a decrease in entropy, internal energy and Gibbs free energy of reaction. Good consistency between the calculated and observed spectral data was found. Also, Sta-SO3H has been developed for the synthesis of acylals (1,1-diacetate) in high yields through the reaction of aldehydes with acetic anhydride at room temperature under solvent-free conditions. The mild conditions, eco-friendliness, excellent yields, short reaction times and use of an inexpensive and reusable catalyst are important features of this method.

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Authors and Affiliations

  1. School of Chemistry, Damghan University, 36716-41167, Damghan, Iran

    Zahra Hoseinabadi, Seied Ali Pourmousavi & Mahdi Zamani

  2. Institute of Biological Sciences, Damghan University, 36716-41167, Damghan, Iran

    Seied Ali Pourmousavi

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  1. Zahra Hoseinabadi
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  2. Seied Ali Pourmousavi
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  3. Mahdi Zamani
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Correspondence to Seied Ali Pourmousavi.

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Hoseinabadi, Z., Pourmousavi, S.A. & Zamani, M. Synthesis of sulfonated carbon-based solid acid as a novel and efficient nanocatalyst for the preparation of highly functionalized piperidines and acylals: a DFT study. Res Chem Intermed 42, 6105–6124 (2016). https://doi.org/10.1007/s11164-016-2448-4

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