Title:Highly Effective Synthesis of 1-thioamidoalkyl-2-naphthols and Tetrahydropyridines Using a Nanostructured Silica-based Catalyst Under Mild Conditions
VOLUME: 23
Author(s):Navid Irannejad-Gheshlaghchaei and Seyed Sajad Sajadikhah*
Affiliation:Department of Chemistry, Payame Noor University, PO Box 19395-3697 Tehran, Department of Chemistry, Payame Noor University, PO Box 19395-3697 Tehran
Keywords:1-Thioamidoalkyl-2-naphthol, Tetrahydropyridine, Solvent-free, Nanostructured catalyst, Nano-
[DSPECDA][HSO4].
Abstract:Aim and Objective: Nano-2-[N',N'-dimethyl-N'-(silica-n-propyl)ethanaminium chloride]-N,N-dimethylaminium
bisulfate (nano-[DSPECDA][HSO4]) was used as a highly effective and heterogeneous silica-based nanostructured catalyst
for the synthesis of 1-thioamidoalkyl-2-naphthols and substituted tetrahydropyridines.
Material and Methods: The expected products were prepared in mild conditions. In this work, three novel 1-
thioamidoalkyl-2-naphthols and two new tetrahydropyridine derivatives were synthesized and characterized by IR, 1H and
13C NMR and Mass spectroscopy.
Results: One-pot multi-component condensation of 2-naphthol with arylaldehydes and thioacetamide catalyzed by nano-
[DSPECDA][HSO4] under green, mild and solvent-free conditions led to 1-thioamidoalkyl-2-naphthols in high yields. The
nanocatalyst was also used for the preparation of functionalized tetrahydropyridines by the one-pot multi-component reaction of anilines, arylaldehydes and ethylacetoacetate under solvent-free and mild conditions.
Conclusion: The reactions results are better compared to the literature in terms of one or more of these factors: yield, time,
and the reaction media. All the products were purified by recrystallization from EtOH, and without column chromatography,
which is good agreement with the green chemistry protocols.
