Novel pseudopolymeric magnetic nanoparticles as a hydrogen bond catalyst for the synthesis of tetrahydrodipyrazolopyridine derivatives under mild reaction conditions

Abstract

In the current work, the design, synthesis, characterization, and catalytic performance of a novel pseudopolymeric magnetic nanoparticles bearing urea linkers were presented. After the synthesis of urea linker, it was applied for the synthesis of pseudopolymeric magnetic nanoparticles. The structure of the synthesized pseudopolymeric magnetic nanoparticles was confirmed by applying different methods including Fourier transform infrared (FT-IR) spectroscopy, energy dispersive X-ray (EDX) analysis, thermo gravimetric analysis/differential thermal analysis (TG/DTG), transmission electron microscopy (TEM), scanning electron microscopy (SEM), vibrating sample magnetometer (VSM), differential reflectance spectroscopy (DRS) and N 2 adsorption-desorption isotherms. The catalytic performance of the titled structure was tested towards the synthesis of tetrahydrodipyrazolopyridine derivatives under mild reaction conditions.

Nanoalkalinecellulose immobilized on magnetic nanoparticles as a green catalyst for the synthesis of tetrahydrodipyrazolopyridines and mechanistic insights under base catalysis

“…These properties provide multiactive sites, high diffusion power, uniformity, and well dispersion of catalyst in the aqueous medium of reaction to activate the reactants in nanopores of catalyst and directing the reaction energy path to the rapid yielding of product. The 33% decrease in the THDPP1 yield for a similar reaction in EtOH supports this interpretation (Figure 7 1 Choline chloride/urea, 110 C 30 92 Vanegas et al [35] 2 Ultrasonic, H 2 O, 50 C 120 95 Shabalala et al [36] 3 Pseudopolymeric nanoparticles, EtOH, r.t. 30 90 Dashteh et al [37] 4 Reflux, EtOH 300 72 Dabiri et al [28] 5 F e 3 O 4 @KCC-1-nPr-NH 2 , ethanol, reflux 30 92 Azizi et al [14] 6 Co4ChDES, H 2 O, 60 C 15 94 Tamaddon and Khorram [31] 7 F e 3 O 4 @NAC, H 2 O, r.t. 10 97 This work…”

MgFe2O4@Tris magnetic nanoparticles: an effective and powerful catalyst for one-pot synthesis of pyrazolopyranopyrimidine and tetrahydrodipyrazolopyridine derivatives

“…They are compounds with a cyclic structure that have at least one carbon atom and at least one heteroatom such as O, N, or S in their structure. Pyrazolopyranopyrimidines 15 and tetrahydrodipyrazolopyridines 16 are two important classes of nitrogen-containing heterocyclic compounds with diverse applications. Pyrazolopyranopyrimidines are a group of polycyclic-fused heterocyclic compounds, consisting of rings containing pyrimidine, pyran, and pyrazole.…”

Catalyst-free synthesis of tetrahydrodipyrazolopyridines via an one-pot tandem and green pseudo-six-component reaction in water

“…A common protocol for the synthesis of THDPP is the reaction of aldehydes, hydrazine hydrate, ethyl acetoacetate, and ammonium acetate in a multi-component manner with the presence of a catalyst. Previously, pseudopolymeric magnetic nanoparticles [ 13 ], KCC-1-NH 2 -DPA [ 14 ], CuFe 2 O 4 @HNTs [ 15 ], acetic acid [ 16 ], and carbonaceous material (CSO 3 H) [ 17 ], Fe 3 O 4 /KCC1/IL/HPWMNPs [ 24 ], Nano-CdZr 4 (PO 4 ) 6 [ 25 ], Nano-Fe 3 O 4 @SiO 2 –SO 3 H [ 23 ], FeNi 3 -ILs MNPs [ 21 ], Nano-CuCr 2 O 4 [ 26 ], Nano-ovalbumin [ 20 ], M(II)/Schiff base@MWCNT-Fe 3 O 4 /SiO 2 [ 27 ]. Meanwhile, a catalyst free protocol using ammonium carbonate instead of ammonium acetate has been reported [ 16 ], Ammonium carbonate is a basic salt and can catalysis the synthesis of THDPP’s.…”