Multicomponent Synthesis of Tetrahydrobenzo[a]xanthene and Tetrahydrobenzo[a]acridine Derivatives using Sulfonated Multi-Walled Carbon Nanotubes as Heterogeneous Nanocatalysts

Iranian Journal of Catalysis

مقاله 7، دوره 12، شماره 2، شهریور 2022، صفحه 189-205   

نوع مقاله: Articles

شناسه دیجیتال (DOI): 10.30495/ijc.2022.1955651.1924

نویسندگان

Shakir Mahmood Saied¹؛ Mohanad Yakdhan Saleh^{* 2}؛ Ahmed M. Hamdoon³

¹Department of Medical Laboratory Techniques, Al-Noor University College, Bartella, Iraq

²Department of Chemistry, College of Education for Pure Science, Mosul University, Mosul-Iraq

³Branch of Basic Science, College of Agriculture and Forestry, University of Mosul, Iraq

چکیده

This study is the first report of the application of sulfonated multi-walled carbon nanotubes (MWCNTs-SO₃H) in the synthesis of tetrahydrobenzo[a]xanthene and tetrahydrobenzo[a]acridine derivatives. The catalyst was prepared via a chemical approach and the sulfonated groups were attached to the side-wall of MWCNTs with total density of 2.58 mmol.g^-1. In order to prove functionalization of the MWCNTs-SO₃H, the catalyst was characterized using FE-SEM, TEM, FT-IR, and Raman spectroscopy techniques. A three-component reaction including 2-naphthol, dimedone, and aromatic aldehydes were applied in the synthesis of tetrahydrobenzo[a]xanthene in the presence of 15.5 mol% of MWCNTs-SO₃H under solvent-free conditions. Also, a four-component reaction including 2-naphthol, dimedone, aromatic aldehydes, and ammonium chloride was used in the synthesis of tetrahydrobenzo[a]acridine in the presence of 12.9 mol% of MWCNTs-SO₃H under solvent-free conditions. All the derivatives of tetrahydrobenzo[a]xanthene and tetrahydrobenzo[a]acridine were obtained in good to excellent yields. The MWCNTs-SO₃H was reused in seven consequent catalytic cycles without loss of their catalytic activity.

کلیدواژه‌ها

Multicomponent؛ Carbon nanotubes؛ Catalyst؛ Heterogeneous؛ Xanthene؛ Acridine

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Supporting Information.pdf

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