Magnetite Nanoparticles-Supported APTES as a Powerful and Recoverable Nanocatalyst for the Preparation of 2-Amino-5,10-dihydro- 5,10-dioxo-4H-benzo[g]chromenes and Tetrahydrobenzo[g]quinoline-5,10- diones

Title:Magnetite Nanoparticles-Supported APTES as a Powerful and Recoverable Nanocatalyst for the Preparation of 2-Amino-5,10-dihydro- 5,10-dioxo-4H-benzo[g]chromenes and Tetrahydrobenzo[g]quinoline-5,10- diones

Volume: 20 Issue: 1

Author(s): Mohammad Ali Ghasemzadeh, Zahra Elyasi, Mina Azimi-Nasrabad and Boshra Mirhosseini-Eshkevari

Affiliation:

Keywords: Fe₃O₄@SiO₂-NH₂, nanocomposite, multi-component reaction, core–shell, benzo[g]chromene, tetrahydrobenzo[g] quinoline-5, 10-dione.

Abstract: Aim and Objective: This study introduces a green and effective approach for the preparation of biologically-active heterocyclic compounds including 2-amino-5,10-dihydro-5,10-dioxo-4Hbenzo[ g]chromenes and tetrahydrobenzo[g]quinoline-5,10-diones using one-pot multi-component reactions in the presence of Fe₃O₄@SiO₂-NH₂ nanocomposite. The preparation and use of aminofunctionalized Fe₃O₄@SiO₂ as a powerful and reusable nanocatalyst is described. The catalyst was characterized by spectral techniques including FT-IR, SEM, XRD, EDX and VSM analysis. This method offers the advantages of high yields, short reaction times, comfortable work-up and reusability of the catalyst.

Material and Method: The amino-functionalization silica-coated magnetite nanocomposite was prepared by three step method and the structure elucidation of the nanocatalyst has been done using various spectroscopic analyses. Then, the Fe₃O₄@SiO₂-NH₂ nanocomposite was used in the multicomponent synthesis of 2-amino-5,10-dihydro-5,10-dioxo-4H-benzo[g]chromenes and tetrahydrobenzo[g]quinoline-5,10-diones under reflux conditions. All of the products were analyzed with m.p., ¹H NMR, ¹³C NMR and FT-IR spectroscopy techniques. The study on the recoverability of the nanocatalyst showed the recovered Fe₃O₄@SiO₂-NH₂ nanocomposite could be reused sixth consecutive times with a little-decreased activity.

Results: Amino-functionalized SiO₂ coated Fe₃O₄ nanocomposite exhibited superparamagnetic behavior and strong magnetization at room temperature. The average crystallite sizes of the catalyst was about 50-60 nm. The obtained magnetic nanocomposite showed excellent catalytic activity as a new heterogeneous magnetic catalyst for the synthesis of some benzo[g]chromenes and tetrahydrobenzo[g]quinoline-5,10-diones. We propose that NH₂ groups on the surfaces of nanocomposite act as the Brønsted base and cause to dehydrogenation of substrates to promote the reactions.

Conclusion: It was found that Fe₃O₄@SiO₂-NH₂ nanocomposite act as an eco-friendly and efficient catalyst for one-pot synthesis of three/four component condensation reactions. In this research, aminofunctionalized Fe₃O₄@SiO₂ was used as recoverable catalyst for the synthesis of 2-amino-5,10- dihydro-5,10-dioxo-4H-benzo[g]chromenes and tetrahydrobenzo[g]quinoline-5,10-diones under reflux conditions. The significant advantages of this method are the reasonably simple work-up, little catalyst loading, short reaction times, excellent yields, non-hygroscopic quality and reusability of the nanocatalyst which is in good agreement with green chemistry disciplines.

Cite this article as:

Ghasemzadeh Ali Mohammad, Elyasi Zahra, Azimi-Nasrabad Mina and Mirhosseini-Eshkevari Boshra, Magnetite Nanoparticles-Supported APTES as a Powerful and Recoverable Nanocatalyst for the Preparation of 2-Amino-5,10-dihydro- 5,10-dioxo-4H-benzo[g]chromenes and Tetrahydrobenzo[g]quinoline-5,10- diones, Combinatorial Chemistry & High Throughput Screening 2017; 20 (1) . https://dx.doi.org/10.2174/1386207319666161223121612

DOI https://dx.doi.org/10.2174/1386207319666161223121612	Print ISSN 1386-2073
Publisher Name Bentham Science Publisher	Online ISSN 1875-5402