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Abstract
A simple, straightforward, and ultrasound-promoted method for the preparation of some highly functionalized tetrahydropyridines reported via pseudo five-component reaction of (hetero)aromatic aldehydes, different anilines, and alkyl acetoacetates in the presence of [N-CH2CO2H-3-pic]+HSO4−, as a novel ionic liquid, in green aqueous medium. The IL was synthesized utilizing simple and easily-handled substrates and characterized by FT-IR, 1H NMR, 13C NMR, GC-MASS, FESEM, EDX, and TGA/DTG techniques. The procedure contains some highlighted aspects which are: (a) performing the MCR in the presence of aqua and sonic waves, as two main important and environmentally benign indexes in green and economic chemistry, (b) high yields of products within short reaction times, (c) convenient work-up procedure, (d) preparing the new IL via simple substrates and procedure.
Highlights
Synthesis of various nitrogen-containing heterocyclic compounds widely attracted in organic chemistry [1, 2]
Some compounds hold THP scaffolds used as corrosion inhibitors for mild steel [12], Recently a wide range of functionalized tetrahydropyridine-3-carboxylates has been synthesized via the reaction of various aldehydes, amines, and β-keto esters utilizing various catalysts under different conditions such as: bromodimethylsulfonium bromide (BDMS) in acetonitrile at room temperature [13], FeCl3/SiO2 NPs in refluxing methanol [14], Bi(III) immobilized on triazine magnetized dendrimer (Fe3O4@TDSN-Bi(III)) in ethanol at room temperature [15], nano-Al2O3/BF3/Fe3O4 at 80 °C [16], CAN in Supplementary Information The online version contains supplementary material available at https://doi.org/10.1007/s42452-021- 04671-9
The Field emission scanning electron microscopy (FESEM) images of the [N-CH2CO2H-3-Pic]+HSO4− IL has been obtained in order to recognize the structure and size of the particles
Summary
Synthesis of various nitrogen-containing heterocyclic compounds widely attracted in organic chemistry [1, 2]. Among different types of N-heterocycles, tetrahydropyridines are significant because of their organic and pharmaceutical attractions [3, 4]. Some compounds hold THP scaffolds used as corrosion inhibitors for mild steel [12], Recently a wide range of functionalized tetrahydropyridine-3-carboxylates has been synthesized via the reaction of various aldehydes, amines, and β-keto esters utilizing various catalysts under different conditions such as: bromodimethylsulfonium bromide (BDMS) in acetonitrile at room temperature [13], FeCl3/SiO2 NPs in refluxing methanol [14], Bi(III) immobilized on triazine magnetized dendrimer (Fe3O4@TDSN-Bi(III)) in ethanol at room temperature [15], nano-Al2O3/BF3/Fe3O4 at 80 °C [16], CAN in
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