Facile synthesis of pyrazolopyridine pharmaceuticals under mild conditions using an algin-functionalized silica-based magnetic nanocatalyst (Alg@SBA-15/Fe3O4)

Fereshte Hassanzadeh-Afruzi; Zeinab Amiri-Khamakani; Mahdi Saeidirad; Mohammad Mehdi Salehi; Reza Taheri-Ledari; Ali Maleki

doi:10.1039/d2ra07228a

Facile synthesis of pyrazolopyridine pharmaceuticals under mild conditions using an algin-functionalized silica-based magnetic nanocatalyst (Alg@SBA-15/Fe₃O₄)

RSC Adv. 2023 Apr 3;13(15):10367-10378. doi: 10.1039/d2ra07228a. eCollection 2023 Mar 27.

Authors

Fereshte Hassanzadeh-Afruzi¹, Zeinab Amiri-Khamakani¹, Mahdi Saeidirad¹, Mohammad Mehdi Salehi¹, Reza Taheri-Ledari¹, Ali Maleki¹

Affiliation

¹ Catalysts and Organic Synthesis Research Laboratory, Department of Chemistry, Iran University of Science and Technology Tehran 16846-13114 Iran maleki@iust.ac.ir +98-21-73021584 +98-21-73228313.

Abstract

Pyrazolopyridines are common scaffolds in various bioactive compounds, which have several therapeutic effects and unique pharmacological properties. In this study, we fabricated a novel environmentally friendly silica-based nanocomposite as a multifunctional catalytic system for the synthesis of pyrazolopyridine derivatives. This novel heterogeneous nanocomposite named Alg@SBA-15/Fe₃O₄ (Alg stands for alginic acid), was prepared in several steps. In this regard, SBA-15 was synthesized by the hydrothermal method. Next, it was magnetized by Fe₃O₄ nanoparticles via an in situ co-precipitation process. Then, SBA-15/Fe₃O₄ particles were functionalized with 3-minopropyltriethoxysilane (APTES). Afterward, Alg@SBA-15/Fe₃O₄ was obtained by a nucleophilic substitution reaction between SBA-15/Fe₃O₄-NH₂ and an as-synthesized methyl-esterified alginic. Different analyses such as Fourier-transform infrared (FTIR), energy-dispersive X-ray (EDX) spectroscopy, field-emission scanning-electron microscopy (FESEM), vibrating-sample magnetometer (VSM), X-ray diffraction (XRD), thermogravimetric analysis (TGA), and BET (Brunauer-Emmett-Teller) have been used to confirm the structure of the fabricated catalyst. The magnetic properties of the Alg@SBA-15/Fe₃O₄ catalytic system imparted by Fe₃O₄ MNPs enable it to be conveniently isolated from the reaction mixture by using an external magnet. According to the obtained results, the prepared nanocatalyst has high thermal stability and it lost approximately 26% of its weight up to 800 °C. Interestingly, a small amount of prepared nanocatalyst (0.02 g) has shown excellent catalytic performance in the synthesis of pyrazolopyridine derivatives (90-97%) in a short reaction time (20-30 min) at room temperature which can be attributed to its porous structure and large surface area, and the presence of many acidic and basic functional groups. In general, it can be argued that the Alg@SBA-15/Fe₃O₄ nanocomposite deserves more attention due to its non-toxicity, ease of preparation, good recyclability, and its high catalytic efficiency.