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Highly effective synthesis of 1-thioamidoalkyl-2-naphthols and tetrahydropyridines using a nanostructured silica-based catalyst under mild conditions

Author(s):

Navid Irannejad-Gheshlaghchaei and Seyed Sajad Sajadikhah*   Pages 1 - 12 ( 12 )

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.

Keywords:

1-Thioamidoalkyl-2-naphthol, Tetrahydropyridine, Solvent-free, Nanostructured catalyst, Nano- [DSPECDA][HSO4].

Affiliation:

Department of Chemistry, Payame Noor University, PO Box 19395-3697 Tehran, Department of Chemistry, Payame Noor University, PO Box 19395-3697 Tehran



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