Design, synthesis, characterization, and physical property determination of a new ionic liquid: the preparation of triaz
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Design, synthesis, characterization, and physical property determination of a new ionic liquid: the preparation of triazolo‑pyrimidines at room temperature under metal‑free conditions Zohreh Shahnavaz1 · Nader Ghaffari Khaligh1 · Taraneh Mihankhah2 · Mohd Rafie Johan1 Received: 7 April 2020 / Accepted: 31 July 2020 © Springer Nature B.V. 2020
Abstract A new ionic liquid is synthesized, and its chemical structure is characterized by FTIR, 1D NMR and 2D NMR, and mass analyses. The thermal behavior and thermal stability of this ionic liquid are investigated. The results approved the formation of 4,4ʹ-trimethylene-N,Nʹ-dipiperidinium sulfate instead of 4,4ʹ-trimethylene-N,Nʹdipiperidinium hydrogen sulfate. Moreover, the synthesis of triazolo-pyrimidine derivatives was successfully conducted in the presence of new ionic liquid at room temperature under metal-free conditions, which demonstrated the catalytic efficiency of this ionic liquid. The workup was carried out without the utilization of high-cost column chromatography. After extraction of desired products, the residual ionic liquid could be recycled and reused in the next runs. New ionic liquid exhibited high catalytic activity even after fifth run with no significant change in the chemical structure. Keywords Ionic liquid · Structure elucidation · Heterocycles · Three-component reaction · Waste prevention
Electronic supplementary material The online version of this article (https://doi.org/10.1007/s1116 4-020-04226-4) contains supplementary material, which is available to authorized users. * Nader Ghaffari Khaligh [email protected]; [email protected] 1
Nanotechnology and Catalysis Research Center, Institute of Postgraduate Studies, University of Malaya, 50603 Kuala Lumpur, Malaysia
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Environmental Research Laboratory, Department of Water and Environmental Engineering, School of Civil Engineering, Iran University of Science and Technology, Tehran 16765‑163, Iran
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Introduction Catalysis is a vital topic in organic chemistry which has been employed in a broad range of sectors, products, and processes. The current trend in catalysis research is to design greener catalysts and eco-friendly technologies, as well as develop the activities toward sustainability and study the activity of catalysts under realistic conditions regarding temperature and pressure. The one-pot multicomponent processes have been employed in the construction of complex and diverse heterocyclic cores along with decreasing the synthetic steps [1]. Triazolo-pyrimidines are the nitrogen bicyclic heterocycles, and their biological and pharmacological activities have been extensively reported in the literature [2–10]. Many different synthetic methods have been reported to prepare various derivatives of triazolo-pyrimidine [11, 12]. Triazolo[1,5-a]pyrimidines can be synthesized via three-component condensation of a various substituted aldehydes, C–H acidic compounds, and aminotriazoles in the presence of different catalytic systems [
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