Synthesis, and molecular modeling of bis(3-(piperazine-1-yl)propyl)tungstate (BPPT) nanoparticles, and its first catalytic application for one-pot synthesis of 4H-chromene derivatives

Abstract

A B S T R A C TA novel, nano-sized, bis(3-(piperazine-1-yl)propyl)tungstate (BPPT) is introduced as an efficient and reusable organometallic catalyst which is considered as a heterogeneous Bronsted-Lowry base and applied successfully for one-pot synthesis of methyl 2-amino-4-aryl substituted-4H-chromene derivatives with good to excellent yields. BPPT has been prepared via a two-step route from natrium tungstate salt. At first, the oxygens of Na 2 WO 4 react with 1-bromo-3-chloropropane via nucleophilic substitution to produce bis(3-choloro propyl)tungstate. Then nucleophilic substitution of piperazine with chlorines produced bis(3-(piperazine-1-yl)propyl) tungstate. Bis(3-(piperazine-1-yl)propyl) tungstate, which was called BPPT, characterized by fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), thermal gravimetric analysis (TGA), transmission electron microscopy (TEM) and scanning electron microscope (SEM). The catalyst is heterogeneous, green and recyclable. It is a thermally stable and its handling is easy. Its catalytic activity is very high and leads to the production of 4H-pyran derivatives with good to excellent yields in short reaction times. Furthermore, molecular modeling studies and ADMETox prediction revealed that not only it can inhibit acetylcholinesterase enzyme and act as an anti-Alzheimer agent but also has no variation from Lipinski's rule of five and can be a good candidate as anti-Alzheimer agents. These above-mentioned facts can be countered as advantages of the current protocol.

Graphene oxide immobilized 2-morpholinoethanamine as a versatile acid–base catalyst for synthesis of some heterocyclic compounds and molecular docking study

“…(ref.) 1b 4-NO 2 -C 6 H 4 – 10 96 247–249 32 2b 2-NO 2 -C 6 H 4 – 15 95 258–260 32 3b C 6 H 4 – 18 93 248–250 33 4b 4-OH-C 6 H 4 – 12 92 271–273 34 5b 2-OH-C 6 H 4 – 16 92 267–270 35 6b 2-Cl-C 6 H 4 – 15 95 273–275 34 7b 3-pyridiyl 12 96 250–252 36 1 mmol of 1, 2 and 3 in EtOH/H 2 O. All yields are isolated products.…”

“…Several approaches have been documented for the synthesis of these compounds. Various techniques, including microwaves, ultrasound, and the use of different catalysts like L-proline 25 , ZnO 26 , silica gel/ NaHSO 4 27 , cyanuric chloride 28 , Yb(OTf) 3 29 , γ-cyclodextrin (γ-CD) 30 , MNPs–PhSO 3 H 31 , SO 3 H@carbon 32 , ZIF@ZnTiO 3 33 , bis(3-(piperazine-1-yl) propyl) tungstate 34 , Bismuth nitrate 35 , Silica-Bonded N-Propylpiperazine Sodium n-Propionate 36 , MCM-41 supported cobalt (II) 37 , Fe 3 O 4 @ MCM-41@ Cu-P2C 38 , can all be mentioned as potential methods 39 – 41 . However, these approaches have drawbacks, such as low efficiency, complicated catalyst separation, high cost of the catalyst and the use of hazardous chemicals in catalyst production, and long reaction times.…”