Highly Effective Synthesis of 1-thioamidoalkyl-2-naphthols and Tetrahydropyridines Using a Nanostructured Silica-based Catalyst Under Mild Conditions

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,Iran

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.

Cite this article as:

Irannejad-Gheshlaghchaei Navid and Sajadikhah Sajad Seyed*, Highly Effective Synthesis of 1-thioamidoalkyl-2-naphthols and Tetrahydropyridines Using a Nanostructured Silica-based Catalyst Under Mild Conditions, Combinatorial Chemistry & High Throughput Screening 2021; 24 (8) . https://dx.doi.org/10.2174/1386207323666200914092345

DOI https://dx.doi.org/10.2174/1386207323666200914092345	Print ISSN 1386-2073
Publisher Name Bentham Science Publisher	Online ISSN 1875-5402