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[TEATNM] and [TEATCM] as novel catalysts for the synthesis of pyridine-3,5-dicarbonitriles via anomeric-based oxidation

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A novel ionic liquid (IL) and nanostructured molten salt (NMS) based on triethylammonium were synthesized and characterized. Their catalytic activities for the synthesis of 2-amino-4-aryl-6-(arylamino)pyridine-3,5-dicarbonitriles via a one-pot three-component condensation… Click to show full abstract

A novel ionic liquid (IL) and nanostructured molten salt (NMS) based on triethylammonium were synthesized and characterized. Their catalytic activities for the synthesis of 2-amino-4-aryl-6-(arylamino)pyridine-3,5-dicarbonitriles via a one-pot three-component condensation reaction between several aromatic aldehydes, malononitrile, and aniline derivatives at 50 °C under solvent-free conditions by anomeric-based oxidation (ABO) as a mechanistic approach were examined and suitable results were attained using triethylammonium trinitromethanide [TEATNM] as an ionic liquid catalyst and triethylammonium tricyanomethanide [TEATCM] as a nanostructured molten salt catalyst. The novel ionic liquid (IL) and nanostructured molten salt (NMS) were fully characterized by Fourier transform infrared (FTIR), nuclear magnetic resonance (1H NMR and 13C NMR), mass, thermal gravimetric (TG) and derivative thermal gravimetric (DTG) analysis, differential thermal analysis (DTA), X-ray diffraction patterns (XRD), scanning electron microscopy (SEM), and transmission electron microscopy (TEM) analysis. Both the experimental and theoretical studies have supported the ABO mechanism for the described organic synthetic methods. Given the non-toxic, inexpensive and recyclable characteristics, these reaction conditions are simple and environmentally friendly.

Keywords: microscopy; dicarbonitriles via; based oxidation; anomeric based; pyridine dicarbonitriles

Journal Title: New Journal of Chemistry
Year Published: 2017

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