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

Document Type : Articles

Authors

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

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

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

Abstract

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.

Graphical Abstract

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

Highlights

  • An efficient and reusable sulfonated multi-walled carbon nanotubes were prepared.
  • MWCNTs-SO3H was used in the synthesis of tetrahydrobenzo[a]xanthene and tetrahydrobenzo[a]acridine.
  • All of the reactions were performed under solvent-free conditions.
  • The MWCNTs-SO3H was characterized using FE-SEM, TEM, FT-IR, and Raman spectroscopy.
  • The catalyst could be reused for seven catalytic cycles.

Keywords


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Volume 12, Issue 2
June 2022
Pages 189-205
  • Receive Date: 28 March 2022
  • Revise Date: 14 May 2022
  • Accept Date: 08 June 2022
  • First Publish Date: 08 June 2022