Title:Highly Effective Synthesis of 1-thioamidoalkyl-2-naphthols and Tetrahydropyridines Using a Nanostructured Silica-based Catalyst Under Mild Conditions
VOLUME: 24 ISSUE: 8
Author(s):Navid Irannejad-Gheshlaghchaei and Seyed Sajad Sajadikhah*
Affiliation:Department of Chemistry, Payame Noor University, 19395-3697 Tehran, Department of Chemistry, Payame Noor University, 19395-3697 Tehran
Keywords:1-Thioamidoalkyl-2-naphthol, Tetrahydropyridine, solvent-free, nanostructured catalyst, Nano-[DSPECDA]
[HSO4], nanotechnology.
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 reaction results were found to be 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, being in good agreement with the
green chemistry protocols.
