Tannic acid-poly ethyleneimine magnetic nanoparticles: an efficient and recyclable catalyst for green synthesis of 2,3-dihydroquinazole derivatives

doi:10.21203/rs.3.rs-2524709/v1

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Tannic acid-poly ethyleneimine magnetic nanoparticles: an efficient and recyclable catalyst for green synthesis of 2,3-dihydroquinazole derivatives

https://doi.org/10.21203/rs.3.rs-2524709/v1

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A novel and recyclable catalytic system was prepared by linking polyethyleneimine (PEI) to tannic acid (TA) using 1,3-dibromopropane, as a cross-linker, to afford (TA-PEI) composite during a convenient and inexpensive procedure. Moreover, to increase the efficacy of the catalyst and to reduce the reaction time, magnetization and sulfonation of the prepared nano-catalyst have been properly performed to afford the final TA/PEI/magnetic/sulfonated (TPMS) supramolecular heterogeneous nonmagnetic composite. The TPMS catalytic system was characterized by various spectrometric and analytical techniques including Fourier transform infrared (FT-IR) spectroscopy, field emission scanning electron microscopy (FE-SEM), thermal gravimetric analysis (TGA), X-ray diffraction (XRD), energy-dispersive X-ray spectroscopy (EDX) and vibrating sample magnetometer (VSM). Furthermore, the heterogeneous TPMS nanocomposite catalytic sytem demonstrated excellent catalytic activity for the one-pot synthesis of 2,3-dihydroquinazole derivatives through a green and sustainable procedure to afford desired products in good to excellent yields. The supramolecular TPMS catalytic system have several advantages including easy separation, nature-friendly, eco-friendly, cost-effective, and reduced reaction time. The reusability of TPMS nanocatalyst was also investigated and the results showed that there is not any significant decrease in the efficiency of the catalyst after five reaction cycles.

Biological sciences/Biochemistry/Bioinorganic chemistry

Biological sciences/Biochemistry/Carbohydrates

Biological sciences/Biochemistry/Chemical modification

Physical sciences/Chemistry

Physical sciences/Chemistry/Catalysis

Physical sciences/Chemistry/Coordination chemistry

Physical sciences/Chemistry/Environmental chemistry

Physical sciences/Chemistry/Green chemistry

Physical sciences/Chemistry/Inorganic chemistry

Physical sciences/Chemistry/Materials chemistry

Physical sciences/Chemistry/Medicinal chemistry

Physical sciences/Chemistry/Organic chemistry

Physical sciences/Chemistry/Supramolecular chemistry

Physical sciences/Chemistry/Synthesis

Tannic acid

Polyethyleneimine

magnetic sulfonate nanocatalyst

heterogeneous catalyst

3-dihydroquinazole

Nanoscience^1–2 plays an important role in both academic exploration and industrial sectors with an extensive potential of applications in daily life including sensors, safety, pharmaceutical and various aspects of technology. One of the more interested aspects of nanocatalysis technology ^3–6. Nanocatalysts have showed significant impact on green chemistry due to their high surface area, high catalytic properties and environmental friendliness⁷. One of the more widespread branches of catalytic systems is heterogeneous catalysts and related magnetic nanoparticle (MNP) that have received significant attraction from scientists recently since they have unique properties ⁸. Heterogeneous catalysts are “high-tech” materials that can be separated from the reaction medium by filtration or centrifugation. Therefore, during these processes, a considerable percentage of the catalyst may be wasted⁹. In this regard, not only the magnetization of the catalyst provided an easy separation and prevention of wastage, but also, the magnetization of the catalyst may decrease the reaction time¹⁰. On the other hand, the size of magnetic nanoparticles can be regularly adjusted in the structure and this particle size and morphology can be maintained even after multiple recovery ¹¹. In addition, the valuable properties of MNPs have made them superior and vital materials in different fields of research and technology from the laboratory to industrial scale ⁸ including information storing¹², medicine,¹³ drug delivery,¹⁴magnetic resonance imaging (MRI), ^15–16biomedical applications,^{8, 17–18} and environmental remediation¹⁹ as well as heterogeneous catalysis^20–23. MNPs have several advantages including low cost, easy synthesis, high magnetic ability, easy separation from the reaction medium and excellent reusability. The latest feature being very important due to the high price of the catalytic system that cannot be recovered readily^24–27.One of the drawbacks in the application of MNPs is the agglomeration under magnetic fields, which leads to a decrease in the surface-to-volume ratio and subsequently to a decrease in its catalytic activity²⁸. Therefore, to prevent mentioned aggregation, MNPs must be stabilized by coating with a protecting layer including carbon layers^29–30, organic polymers^31–33 or silica^{23, 34–40}. Moreover, due to high surface area of magnetic nanoparticles and their superparamagnetic properties, they have attracted major consideration. Besides, bio-polymers and biomolecules from natural resources containing different properties including various functional groups, non-toxicity, low cost, biocompatibility, and availability can be grafted to magnetic nano catalytic systems to afford nanomagnetic biopolymers or nanomagnetic biomolecules. The application of bio-polymers and biomolecules has resulted in decreasing heavy metal pollution, which is targeted by green chemistry principles ^41–42. A variety of bio-based materials have been used for the synthesis of novel biocatalysts recently ^{25, 43–48}. Green nanomaterials are now the main focus of research on nanotechnology ^{42, 49}. In addition to existing chemical methods, biomaterials are promising sources of nanoparticles. Therefore, utilizing biomass is developing as a new method for the synthesis of nanoparticles ⁵⁰. One of these important bio-based materials is polyphenols ⁵¹. Polyphenols are natural, abundant and widely spread group of bioactive molecules that have two general categories including flavonoids and phenolic acids. Each group has different subdivisions. Due to special structure of polyphenols, they possess a variety of biological activities ⁵². Up to now, more than 8000 unique molecules of polyphenols have been discovered. The presence of catechol and gallol moieties among subdivisions of polyphenols enable them to interact with different materials or substrates through hydrogen bonding, hydrophobic interactions, π interactions, covalent bonding, metal coordination, and electrostatic interactions ⁵². Plant biomolecules, such as tannins, can be used to produce nanoparticles in an environmentally friendly way ⁵³. They often accumulate in large quantities in leaves, fruits, wood and bark, and are involved in plant protection against vegetarians, pathogens and decay ⁵⁴. Tannic acids have antioxidant properties and are utilized as a healing agent for burns and physical injuries ⁵⁵. Due to the extensive application and properties of tannic acid, as a plant polyphenol, in different sciences, scientists have dramatically considered it recently ⁵⁶. One of the important properties of tannic acid is the ability to adhere to numerous kinds of substrates, including organic and/or inorganic ones, hydrophilic and/or hydrophobic ones, spots and/or planar ones, etc. Based on the strong interaction between tannic acid and mentioned substrates, the joining is generally vigorous. Generally, tannic acid has been used to modify the polymeric membrane’s surface. Because of the existence of numerous hydrophobic regions on the membrane, hydrophobic interaction, through hydrogen bonds, in the modification process is a vital factor ^57–60. The pK_a of tannic acid is in the range of 2.5–8.5 which shows weak acidic properties ^61–63. The main difference is probably resulted from various sources. The behavior of tannic acid has a direct relation to pH, when the pH is higher than pKa, it acts like a poly-anion. Therefore, adhering to substrates can be readily accomplished ^64–65. Moreover, the structure of tannic acid complexes is also controlled by several factors including pH, ionic strength, other ligands, etc.

(Fig. 1) shows that, at pH < 2 the main tannic acid/Fe³⁺ coordination state is mono-complex, at 3 < pH < 6 bis-complex and at pH > 7 tris-complex ^{63, 66–68}. The lone pair electrons of the phenolic hydroxyl groups of tannic acid can interact through coordination to metal centers and this can be employed for modification of substrates that contains metal and/or metallic oxide ^69–74.

Polyethyleneimine (PEI) is a water-soluble cationic polymer^75–76, that has been extensively employed in different fields of science comprising isolation, purification drug/gene delivery^77–79, CO₂ adsorption ⁸⁰ nucleotide, cell, and enzyme immobilization ⁸¹. In addition, PEI is a capping agent and because of the presence of NH₂ groups, acts as a reducing and stabilizing agent simultaneously ^82–85. PEI is a highly branched polymer that contains a proportion of amine groups, 1:2:1 for primary amine, secondary, and tertiary amine, declaring that PEI can afford a wider range of amine groups than regular amine compounds ^86–87. More attractively, PEI is an eco-friendly and water-soluble viscous liquid ⁸⁷. The molecular weight of PEI chains has significant impacts on its application in different fields including drug or gene delivery and pharmaceutical. These effects are separated from those of ammonia and have been investigated in a wide range of molecular weights ^88–91. The more increase in the PEI weight, the more diversity in the application. The existence of amine groups in PEI provides important properties such as good solubility and better bonding ability to metals and other related materials⁹². One-pot multicomponent reactions (MCRs) are one of the most successful and environment-friendly methods for the production of organic compounds comprising highly valuable N-containing heterocycles with different structures and molecular complexity using a simple process. As a developing process for the preparation of medicinal compounds, this method allows the expansion of many chemical and pharmaceutical compounds with more structural diversity ^93–96. Quinazoline heterocycles are an important group of nitrogen-containing cyclic compounds. These heterocycles are vital in the development of pharmaceuticals and provide a variety of biologically active scaffolds^97–98. It has been reported that quinazoline derivatives have various biological and therapeutic properties including antibacterial, anti-inflammatory, antifungul, anticancer, anti-plasmodial, anti-tumor, antimicrobial and antioxidant ability ^99–101. The first synthesis of quinazoline was reported in 1869, in which 2-ehoxy-4 (3H)-quinazolinone was prepared from anthranilic acid and cyanogen in ethanol. 2,3-dihydroquinazolin have attracted a lot of attention in recent decades ¹⁰². The presence of quinazolinone ring creates a benzopyridine aromatic system ¹⁰³. Because of the high medicinal potential of these compounds, various methods have been proposed for their synthesis from chemical sources. Different catalysts have been used for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones including copper-benzenesulfonate ¹⁰⁴, starch sulfate ¹⁰⁵, magnetic Fe₃O₄ nanoparticles ^106–107, silica sulfuric acid ¹⁰⁸, b-cyclodextrin-SO₃H ¹⁰⁶, and aluminiumm ethanesulfonate ¹⁰⁹. The most common method for the synthesis of these compounds is the three-component reaction among isatoic anhydride, aldehyde, and amines or ammonium salts in the presence of acid catalysts. However, due to the corrosion and toxicity of acid catalysts, basic catalysts have been used in recent years to promote this reaction ¹¹⁰. A large number of 2,3-hydroquinazoline derivatives have been synthesized as active pharmaceutical precursors. 2,3-dihydroquinazole derivatives have various medicinal properties comprising anti-cancer, anticonvulsant, analgesic, anti-inflammatory, high blood pressure, antifungal and antitumor activity ¹¹¹. Some catalysts employed for the synthesis of hydroquinazolines have several disadvantages such as low efficiency, long reaction time, harsh reaction conditions, and the use of expensive and toxic materials. For these reasons, the demand for the production of catalysts with high efficiency, reduced reaction time and cost-effectiveness has increased. The composition of TA/PEI is synthesized in a spherical structure by the electrostatic interaction between ammonium groups of PEI and phenolic TA molecules ¹¹². In continuing our performed and ongoing researches for the preparation of various catalytic systems to use in the green synthesis of different heterocyclic scaffolds^{40, 113–114}, we herein presented the synthesis, modification and characterizations of a novel efficient Fe₃O₄@TPMS nanomagnetic composite by using tannic acid, PEI, 1,3- dromobropropane, FeCl₃, FeCl₂ and chlorosulfuric acid. To the best of our knowledge, this is the first report in this regrad and the prepared magnetically reusable organocatalyst demonstrated excellent thermal and magnetic stability, and specific morphology to promote the synthesis of 2,3-dihydroquinazole derivatives in green mild conditions.

General

All chemicals and reagents were purchased from the best international chemical companies, Fluka, Merck, and SigmaAldrich. Melting points are measured by the 9100 electrothermal device. The analytical thin layer chromatography (TLC) was performed utilizing Merck 0.2 mm silica gel 60 F-254 Al-plates. The characterization of the TPMS catalyst was carried out using different spectroscopic, microscopic, and analytical techniques including Shimadzu FTIR-8400S spectrometer, thermal gravitational analysis (TGA), FESEM (TESCAN-MIRA3), EDX (Numerix DXP-X10P), VSM (BHV-55, Riken, Japan), Shimadzu FT-IR-8400S and TEM (Philips CM30), X-ray diffraction (XRD). ¹H NMR spectra were recorded at 500 MHz in DMSO or CDCl₃, as solvent, by using a Bruker DRX-500 Avance spectrometer.

Synthesis of TA / PEI catalyst (TP)

For this synthesis, tannic acid (0.25 g) was dispersed in 25 ml of acetonitrile, then (0.37 g) of polyethyleneimine was gradually added to the mixture and mixed to afford a homogenous phase. After that, (0.2 gr) of K₂CO₃ was added and mixed. Finally, 1 ml of the linker, 1,3- dromobropropane, was added dropwise followed by the addition of (0.28 g) of potassium iodide (KI). The system was put under reflux for 24 h. After a few hours, the color of the mixture turned completely black. The prepared TP was filtered and washed several times with ethanol, and finally dried at 60 ^oC in the oven.

Preparation of Magnetic TP Catalyst (TPM)

TP (0.5 g) was dispersed in 25 ml of distilled water, then the mixture of (1.25 g) of FeCl₃ and (0.6 g) of FeCl₂ were added to the suspension and stirredvigorously.After 20 minutes, (12 ml) of ammonia was poured dropwise under nitrogen atmosphere followed by strong mixing. Next, the mixture was mixed for two h, then the nanomagnetic product was separated by using an external magnet. Finally, the nanomagnetic TA/PEI was rinsed and washed with distilled water¹¹⁵.

Synthesis of TPM sulfonated (TPMS)

To synthesize TPMS, (0.5 g) of TPM nanoparticles was dispersed in 15 ml of DCM, then the premixed of chlorosulfuric acid (3 ml) in 5 ml of DCM was added to the mixture dropwise, then the suspension was stirred for 1 h to afford desired TPMS. Eventually, the product was separated and rinsed with DCM and plenty of water. The complete procedure is illustrated in (Fig. 2). The scaffold of the TP support is shown in (Scheme 1).

Synthesis of 2,3-dihydroquinazoline derivatives using TPMS nanocatalyst (1)

After characterization TPMS nanocomposite (1), the three-component synthesis of 2,3-dihydroquinazole derivatives was chosen to examine its catalytic activity. For this purpose, the condensation, 1 mmol aldehyde (4a, 1 mmol) isatonic anhydride (2, 1 mmol) amine (3, 1 mmol) and TPMS (0.01 g) was selected as the model reaction for the synthesis of desire product (5a) (Table 1). The mentioned amounts were added into 3 ml EtOH, as a solvent, in a 10 ml Round-bottom flask and placed on a magnetic stirrer under reflux conditions. The progression of the reaction was checked by thin-layer chromatography (TLC) using ethyl acetate and n-hexane in the ratio of 3: 1 as a mobile phase. After completion and cooling the reaction to r.t., the mixture was dissolved in hot ethanol, then the nanomagnetic catalyst was separated by using an external magnet bar. The final pure products was prepared by recrystallization and purification of crude products in (EtOH-H₂O) crystallization system. The results are reported in (Table 2).

Mechanism of 2,3-dihydroquinazolin-4(1H)-ones synthesis catalyzed by the TPMS (1)

A reasonable mechanism for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones catalyzed by the TPMS (1) is demonstrated in (Scheme 2). Firstly, isatoic anhydride is activated by TPMS; therefore, the carbonyl group of isatoic anhydride is able to be protonated to form intermediate (I), after that, the amine attacks on the carbonyl to afford intermediate (II). By emission of CO2, intermediate (III) is obtained. Thereafter, the reaction between (III) and TPMS activates the aldehyde, resulting in intermediate (IV). An intramolecular nucleophilic attack from the nitrogen of amid group to the active carbon of the imine moiety, followed by losing one molecule of H₂O, affords cyclized intermediate (V) which is converted to product (VI) via an intramolecular cyclization.

EDX analysis of TP and TPMS nanocatalyst (1)

Through EDX analysis, the rough percentage of elements in the structures can be determined. The presence of C, O, and N elements confirms the formation of TA / PEI catalyst (Fig. 3a), and the observation of C, O, N, Fe, and S elements in (Fig. 3b) showed that the TMPS scaffold is prepared. By comparison between the two analyzes and by considering the existence of S and Fe elements, it can be implied that the TPMS nanocatalyst (1) has been synthesized.

FESEM analysis of TPMS nanocatalyst (1)

To determine the surface morphology and particle size distribution, FESEM analysis is used. As it is clear from the images in (Fig. 4), the scattering of particle size between 17 nm and 27 nm is clearly observed. Having a porous surface and regular dispersion of particles on the surface has confirmed the bonding of two polymers and the immobilization of iron particles and SO₃H groups on the surface.

TGA analysis of TPMS nanocatalyst (1)

TGA analysis shows the behavior of material against heat. The main base of the catalyst is TA and PEI polymers, on the other hand, organic compounds are generally decomposed at about 400 ^oC. As shown in (Fig. 5), about 23% of the mass is lost between 100 to 400 ^oC, and a sharp drop from 400 to 450^oC is seen due to the complete decomposition of organic compounds. The strong connection between two polymers with the linker causes a dramatic rise at the decomposition temperature. After 450°C, the curve has a gentle slope, and at 600°C, the slope is almost zero, which indicates the stability of the magnetic material.

FTIR analysis of (a) TA (b) TPMS (c) TP.

The FTIR spectrum of TA molecules indicates some characteristic bands of phenolic –OH, between 3000 and 3600 cm^-1, and the C=O group depicted at 1697 cm^-1, the stretching mode of aromatic groups located at 1612, 1521, and 1426 cm^-1. furthermore, the FT-IR spectrum of TA/PEI polyplex particles indicates both peaks from initial TA molecules and branched PEI polymer, for instance, the stretching C-H bands at 2950 from branched PEI chains, the C=O peaks at 1702 cm^-1from TA molecules, and the bending N-H band at 1600 cm^-1 from branched PEI chains. The characteristic peak at 580 cm^-1 of TPMS could be ascribed to the lattice absorption of the Fe₃O₄ nanoparticles. The characteristic absorption bands at 1190–1200 cm^-1 and 1020–1130 cm^-1 can be ascribed to the asymmetric and symmetric stretching modes of O=S=O, moreover, the absorption band at 573–629 cm^-1 can be attributed to the stretching mode of S–O. The combination of mentioned spectrums is illustrated in (Fig. 6).

XRD pattern of TPMS nanocatalyst (1)

XRD is a non-destructive method that provides detailed information on the crystallographic structure, chemical composition, and physical properties of materials. XRD pattern for TPMS is illustrated in (Fig. 7). The bifurcated peak at 2θ = 30˚ was the peak index of tannic acid and 2θ = 57.4˚ was the PEI. The peak is located at 2θ = 63˚, 57˚, 43˚, 36˚, 30˚, which indicates that it is magnetic. Overlap is observed in some peaks, which makes them look sharper. According to the registered index card for Fe₃O₄ (card no. JCPDS, 01-088-0315)[111], tannic acid and PEI and the conformity with the provided XRD broad spectrum at 2θ = (20-30), the formation of supramolecular nanomagnetic catalyst has proved. Other observed sharp bands belong to PEI and Fe moiety.

VSM spectrum of TPMS nanocatalyst (1)

The vibrating sample magnetometry (VSM), was the final analysis for the characterization of the catalyst, which has performed at room temperature. VSM has indicated the magnetic feature of TPMS nanocatalyst (1), by using this technique, the saturation magnetization of the catalyst was found to be 29.94 emu/g (Fig. 8). The S shape of the VSM curve has shown the magnetic properties of the catalyst.

The optimization of the reaction conditions has been performed by various changes in different parameters including solvent, catalyst loading, catalyst, temperature and time for the model reaction (Tables 1). The application of the TPMS catalyst (1) for the synthesis of desired products has been investigated as well in (Table 2).

To evaluate the best catalyst, all three catalysts have been placed in the same conditions and the same reaction that can be seen in the first three rows in (Table 1), which according to the obtained results; TPMS had the shortest reaction time and maximum efficiency (Entry 3). Moreover, in other rows, the optimization of the model reaction by employing TPMS, as catalyst, in different solvents, reaction time and various amounts of the catalyst has been performed. The best situation was observed in (Entry 10)

After determining the superior catalyst and the best reaction conditions in the model reaction, other 2,3-dihydroquinazoline-4 (1H) -one derivatives were synthesized by using ammonium acetate and various types of aldehydes and the results are illustrated in (Table 2), which indicates the high compatibility of the catalyst whit the reaction.

Selected spectral data of representative compounds

1-(4-(dimethylamine) phenyl)-2,3-dihydroquinazolin- 4(1)-one (5h):

White solid: m.p. 229-230 °C. ¹H NMR (500 MHz, DMSO-d6): δ (ppm) 8.07 (s, 1H), 7.61 (d, J = 8.0 Hz, 1H), 7.30 (d, J = 12.0 Hz, 1H) 7.25-7.23 (m, 2H), 7.21 (d, J = 8.0 Hz, 1H) 6.92 (d, J = 8.0 Hz, 2H) 6.74-6.72 (m, 1H), 6.68 (s, 1H), 6.65 (s, 1H), 5.64 (s, 3H). FT-IR (KBr): ν_max/cm^-1; 3440 (NH), 1639 (CO), 1400-1500 (C=C), 2927 (C-H).

2-(5-Bromo-2-hydroxyphenyl)-3-phenyl-2,3-dihydroquinazolin-4(1H)-one (5b):

White solid: m.p. 210-217 °C; ¹H NMR (500 MHz, DMSO-d6): δ (ppm) 5.97 (s, 1H, CH), 6.78 - 6.71 (m, 3H, Ph), 7.26 -7.24 (m, 8H, Ph), 7.64 (dd, J = 7.8 Hz, J = 1.2 Hz, 1H, Ph), 10.24 (1H, s, OH); FT-IR (KBr): ν_max / cm^-1; 3400 (NH), 1636 (CO), 1400-1500 (C=C), 2926 (C-H)

This paper presents a new approach for the synthesis of magnetic nanocatalysts of TA/ PEI sulfonates in a simple and environmentally friendly manner. The cationic and anionic bonds between TA / PEI are weak, herein we have used the1,3-dibromopropane linker to overcome this problem, which has created a strong bond. Then, using various spectral and analytical techniques such as FT-IR, UV-VIS, TGA, FE-SEM, XRD, and EDX analysis, the structural properties and functional groups in the magnetic TA / PEI sulfonated nanocatalyst was determined. Finally, the prepared nanocatalyst has been employed in the synthesis of 2,3-dihydroquinazolinederivatives. According to the obtained results, the TPMS catalyst showed high efficiency at short reaction times and can be recycled several times without a significant decrease in its catalytic activity.

Availability of data and materials

All data generated or analyzed during this study are included in this published article [and its supplementary information files].

Acknowledgements

We are grateful for the financial support from The Research Council of Iran University of Science and Technology (IUST), Tehran, Iran (Grant No 160/20969) for their support. We would also like to acknowledge the support of The Iran Nanotechnology Initiative Council (INIC), Iran.

Competing interests

The authors declare no competing interests.

Wang, D.; Astruc, D., The recent development of efficient Earth-abundant transition-metal nanocatalysts. Chemical Society Reviews 2017, 46 (3), 816-854.
Cademartiri, L.; Ozin, G. A., Concepts of nanochemistry. John Wiley & Sons: 2009.
Li, Y.; Somorjai, G. A., Nanoscale advances in catalysis and energy applications. Nano letters 2010, 10 (7), 2289-2295.
Bell, A. T., The impact of nanoscience on heterogeneous catalysis. Science 2003, 299 (5613), 1688-1691.
Zhang, Z.-c.; Xu, B.; Wang, X., Engineering nanointerfaces for nanocatalysis. Chemical Society Reviews 2014, 43 (22), 7870-7886.
Dai, Y.; Wang, Y.; Liu, B.; Yang, Y., Metallic nanocatalysis: an accelerating seamless integration with nanotechnology. Small 2015, 11 (3), 268-289.
Alirezvani, Z.; Dekamin, M. G.; Valiey, E., New hydrogen-bond-enriched 1, 3, 5-tris (2-hydroxyethyl) isocyanurate covalently functionalized MCM-41: An efficient and recoverable hybrid catalyst for convenient synthesis of acridinedione derivatives. ACS omega 2019, 4 (24), 20618-20633.
Bilal, M.; Zhao, Y.; Rasheed, T.; Iqbal, H. M. N., Magnetic nanoparticles as versatile carriers for enzymes immobilization: A review. International Journal of Biological Macromolecules 2018, 120, 2530-2544.
Sudarsanam, P.; Zhong, R.; Van den Bosch, S.; Coman, S. M.; Parvulescu, V. I.; Sels, B. F., Functionalised heterogeneous catalysts for sustainable biomass valorisation. Chemical Society Reviews 2018, 47 (22), 8349-8402.
Sadjadi, S.; Lazzara, G.; Heravi, M. M.; Cavallaro, G., Pd supported on magnetic carbon coated halloysite as hydrogenation catalyst: Study of the contribution of carbon layer and magnetization to the catalytic activity. Applied Clay Science 2019, 182, 105299.
Wang, Y.; Zhang, Y.; Hou, C.; He, F.; Liu, M., Facile one-pot assembly of adhesive phenol/Fe III/PEI complexes for preparing magnetic hybrid microcapsules. New Journal of Chemistry 2016, 40 (1), 781-788.
Gdovinová, V.; Tomašovičová, N.; Jeng, S.-C.; Zakutanská, K.; Kula, P.; Kopčanský, P., Memory effect in nematic phase of liquid crystal doped with magnetic and non-magnetic nanoparticles. Journal of Molecular Liquids 2019, 282, 286-291.
Santos, A. G.; da Rocha, G. O.; de Andrade, J. B., Occurrence of the potent mutagens 2- nitrobenzanthrone and 3-nitrobenzanthrone in fine airborne particles. Scientific Reports 2019, 9 (1), 1.
Štorkánová, H.; Oreská, S.; Špiritović, M.; Heřmánková, B.; Bubová, K.; Komarc, M.; Pavelka, K.; Vencovský, J.; Distler, J. H. W.; Šenolt, L.; Bečvář, R.; Tomčík, M., Plasma Hsp90 levels in patients with systemic sclerosis and relation to lung and skin involvement: a cross-sectional and longitudinal study. Scientific Reports 2021, 11 (1), 1.
Bai, C.; Hu, P.; Liu, N.; Feng, G.; Liu, D.; Chen, Y.; Ma, M.; Gu, N.; Zhang, Y., Synthesis of Ultrasmall Fe3O4 Nanoparticles as T1–T2 Dual-Modal Magnetic Resonance Imaging Contrast Agents in Rabbit Hepatic Tumors. ACS Applied Nano Materials 2020, 3 (4), 3585-3595.
Yan, K.; Li, P.; Zhu, H.; Zhou, Y.; Ding, J.; Shen, J.; Li, Z.; Xu, Z.; Chu, P. K., Recent advances in multifunctional magnetic nanoparticles and applications to biomedical diagnosis and treatment. RSC Advances 2013, 3 (27), 10598-10618.
Garanina, A. S.; Naumenko, V. A.; Nikitin, A. A.; Myrovali, E.; Petukhova, A. Y.; Klimyuk, S. V.; Nalench, Y. A.; Ilyasov, A. R.; Vodopyanov, S. S.; Erofeev, A. S.; Gorelkin, P. V.; Angelakeris, M.; Savchenko, A. G.; Wiedwald, U.; Majouga Dr, A. G.; Abakumov, M. A., Temperature-controlled magnetic nanoparticles hyperthermia inhibits primary tumor growth and metastases dissemination. Nanomedicine: Nanotechnology, Biology and Medicine 2020, 25, 102171.
Lavorato, G. C.; Das, R.; Alonso Masa, J.; Phan, M.-H.; Srikanth, H., Hybrid magnetic nanoparticles as efficient nanoheaters in biomedical applications. Nanoscale Advances 2021, 3 (4), 867-888.
Wang, Z.; Guo, J.; Ma, J.; Shao, L., Highly regenerable alkali-resistant magnetic nanoparticles inspired by mussels for rapid selective dye removal offer high-efficiency environmental remediation. Journal of Materials Chemistry A 2015, 3 (39), 19960-19968.
Mrówczyński, R.; Nan, A.; Liebscher, J., Magnetic nanoparticle-supported organocatalysts – an efficient way of recycling and reuse. RSC Advances 2014, 4 (12), 5927-5952.
Saranya, S.; Aneeja, T.; Neetha, M.; Anilkumar, G., Recent advances in the iron‐catalysed multicomponent reactions. Applied Organometallic Chemistry 2020, 34 (12), e5991.
Zhang, Q.; Yang, X.; Guan, J., Applications of Magnetic Nanomaterials in Heterogeneous Catalysis. ACS Applied Nano Materials 2019, 2 (8), 4681-4697.
Ishani, M.; Dekamin, M. G.; Alirezvani, Z., Superparamagnetic silica core-shell hybrid attached to graphene oxide as a promising recoverable catalyst for expeditious synthesis of TMS-protected cyanohydrins. Journal of Colloid and Interface Science 2018, 521, 232-241.
Karami, S.; Dekamin, M. G.; Valiey, E.; Shakib, P., DABA MNPs: a new and efficient magnetic bifunctional nanocatalyst for the green synthesis of biologically active pyrano[2,3-c]pyrazole and benzylpyrazolyl coumarin derivatives. New Journal of Chemistry 2020, 44 (33), 13952-13961.
Alirezvani, Z.; Dekamin, M. G.; Valiey, E., Cu(II) and magnetite nanoparticles decorated melamine-functionalized chitosan: A synergistic multifunctional catalyst for sustainable cascade oxidation of benzyl alcohols/Knoevenagel condensation. Scientific Reports 2019, 9 (1), 17758.
Simonsen, G.; Strand, M.; Øye, G., Potential applications of magnetic nanoparticles within separation in the petroleum industry. Journal of Petroleum Science and Engineering 2018, 165, 488-495.
Zhou, K.; Zhou, X.; Liu, J.; Huang, Z., Application of magnetic nanoparticles in petroleum industry: A review. Journal of Petroleum Science and Engineering 2020, 188, 106943.
Yeap, S. P.; Lim, J.; Ooi, B. S.; Ahmad, A. L., Agglomeration, colloidal stability, and magnetic separation of magnetic nanoparticles: collective influences on environmental engineering applications. Journal of Nanoparticle Research 2017, 19 (11), 368.
Trifonov, A.; Stemmer, A.; Tel-Vered, R., Carbon-coated magnetic nanoparticles as a removable protection layer extending the operation lifetime of bilirubin oxidase-based bioelectrode. Bioelectrochemistry 2021, 137, 107640.
Martínez-Prieto, L. M.; Marbaix, J.; Asensio, J. M.; Cerezo-Navarrete, C.; Fazzini, P.-F.; Soulantica, K.; Chaudret, B.; Corma, A., Ultrastable Magnetic Nanoparticles Encapsulated in Carbon for Magnetically Induced Catalysis. ACS Applied Nano Materials 2020, 3 (7), 7076-7087.
Ziegler-Borowska, M., Magnetic nanoparticles coated with aminated starch for HSA immobilization- simple and fast polymer surface functionalization. International Journal of Biological Macromolecules 2019, 136, 106-114.
Rostami, N.; Dekamin, M. G.; Valiey, E., Chitosan-EDTA-Cellulose bio-based network: A recyclable multifunctional organocatalyst for green and expeditious synthesis of Hantzsch esters. Carbohydrate Polymer Technologies and Applications 2023, 5, 100279.
Valiey, E.; Dekamin, M. G.; Bondarian, S., Sulfamic acid grafted to cross-linked chitosan by dendritic units: a bio-based, highly efficient and heterogeneous organocatalyst for green synthesis of 2, 3-dihydroquinazoline derivatives. RSC advances 2023, 13 (1), 320-334.
Khazaei, A.; Khazaei, M.; Nasrollahzadeh, M., Nano-Fe3O4@SiO2 supported Pd(0) as a magnetically recoverable nanocatalyst for Suzuki coupling reaction in the presence of waste eggshell as low-cost natural base. Tetrahedron 2017, 73 (38), 5624-5633.
de Mendonça, E. S. D. T.; de Faria, A. C. B.; Dias, S. C. L.; Aragón, F. F. H.; Mantilla, J. C.; Coaquira, J. A. H.; Dias, J. A., Effects of silica coating on the magnetic properties of magnetite nanoparticles. Surfaces and Interfaces 2019, 14, 34-43.
Gad, Y. H.; Elbarbary, A. M., Radiation synthesis of Fe3O4/SiO2/glycidyl methacrylate/acrylonitrile nanocomposite for adsorption of basic violet 7 dye: Kinetic, isotherm, and thermodynamic study. Applied Organometallic Chemistry 2021, 35 (7), e6258.
Sam, M.; Dekamin, M. G.; Alirezvani, Z., Dendrons containing boric acid and 1,3,5-tris(2-hydroxyethyl)isocyanurate covalently attached to silica-coated magnetite for the expeditious synthesis of Hantzsch esters. Scientific Reports 2021, 11 (1), 2399.
FaniMoghadam, H.; Dekamin, M. G.; Rostami, N., Para-Aminobenzoic acid grafted on silica-coated magnetic nanoparticles: a highly efficient and synergistic organocatalyst for on-water synthesis of 2,3-dihydroquinazolin-4(1H)-ones. Research on Chemical Intermediates 2022, 48 (7), 3061-3089.
Fattahi, B.; Dekamin, M. G., Fe3O4/SiO2 decorated trimesic acid-melamine nanocomposite: a reusable supramolecular organocatalyst for efficient multicomponent synthesis of imidazole derivatives. Scientific Reports 2023, 13 (1), 401.
Valiey, E.; Dekamin, M. G., Pyromellitic diamide–diacid bridged mesoporous organosilica nanospheres with controllable morphologies: a novel PMO for the facile and expeditious synthesis of imidazole derivatives. Nanoscale Advances 2022, 4 (1), 294-308.
Kheilkordi, Z.; Ziarani, G. M.; Badiei, A.; Sillanpää, M., Recent advances in the application of magnetic bio-polymers as catalysts in multicomponent reactions. RSC advances 2022, 12 (20), 12672-12701.
Rani, M.; Keshu; Shanker, U., Chapter 3 - Green nanomaterials: An overview. In Green Functionalized Nanomaterials for Environmental Applications, Shanker, U.; Hussain, C. M.; Rani, M., Eds. Elsevier: 2022; pp 43-80.
Nasrollahzadeh, M.; Shafiei, N.; Nezafat, Z.; Soheili Bidgoli, N. S.; Soleimani, F., Recent progresses in the application of cellulose, starch, alginate, gum, pectin, chitin and chitosan based (nano)catalysts in sustainable and selective oxidation reactions: A review. Carbohydrate Polymers 2020, 241, 116353.
Dohendou, M.; Pakzad, K.; Nezafat, Z.; Nasrollahzadeh, M.; Dekamin, M. G., Progresses in chitin, chitosan, starch, cellulose, pectin, alginate, gelatin and gum based (nano) catalysts for the Heck coupling reactions: A review. International Journal of Biological Macromolecules 2021, 192, 771-819.
Dekamin, M. G.; Azimoshan, M.; Ramezani, L., Chitosan: a highly efficient renewable and recoverable bio-polymer catalyst for the expeditious synthesis of α-amino nitriles and imines under mild conditions. Green Chemistry 2013, 15 (3), 811-820.
Dekamin, M. G.; Kazemi, E.; Karimi, Z.; Mohammadalipoor, M.; Naimi-Jamal, M. R., Chitosan: An efficient biomacromolecule support for synergic catalyzing of Hantzsch esters by CuSO4. International journal of biological macromolecules 2016, 93, 767-774.
Valiey, E.; Dekamin, M. G.; Alirezvani, Z., Melamine-modified chitosan materials: An efficient and recyclable bifunctional organocatalyst for green synthesis of densely functionalized bioactive dihydropyrano [2, 3-c] pyrazole and benzylpyrazolyl coumarin derivatives. International journal of biological macromolecules 2019, 129, 407-421.
Rajabi, M. D., M.; Dekamin, M.G. , Synthesis of carboxymethyl chitosan and its derivatives using KI and/or ultrasonication,. Chem proceeding, the 26th International Electronic Conference on Synthetic Organic Chemistry, MDPI 15–30 November 2022.
Lu, Y.; Ozcan, S., Green nanomaterials: On track for a sustainable future. Nano Today 2015, 10 (4), 417-420.
Herrera-Becerra, R.; Rius, J.; Zorrilla, C., Tannin biosynthesis of iron oxide nanoparticles. Applied Physics A 2010, 100 (2), 453-459.
Yu, L.-Q.; Wang, H.; Chen, S.-L.; Wen, T.-E.; Huang, B.-C.; Jin, R.-C., Biomass derived Fe-N/C catalyst for efficiently catalyzing oxygen reduction reaction in both alkaline and neutral pH conditions. Chinese Chemical Letters 2023, 34 (1), 107236.
Abbas, M.; Saeed, F.; Anjum, F. M.; Afzaal, M.; Tufail, T.; Bashir, M. S.; Ishtiaq, A.; Hussain, S.; Suleria, H. A. R., Natural polyphenols: An overview. International Journal of Food Properties 2017, 20 (8), 1689-1699.
Ali, S. S.; Zia, M. K.; Siddiqui, T.; Khan, F. H., Binding interaction of sheep alpha-2-macroglobulin and tannic acid: A spectroscopic and thermodynamic study. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2018, 204, 748-753.
Fraga-Corral, M.; García-Oliveira, P.; Pereira, A. G.; Lourenço-Lopes, C.; Jimenez-Lopez, C.; Prieto, M. A.; Simal-Gandara, J., Technological application of tannin-based extracts. Molecules 2020, 25 (3), 614.
Ninan, N.; Forget, A.; Shastri, V. P.; Voelcker, N. H.; Blencowe, A., Antibacterial and anti-inflammatory pH-responsive tannic acid-carboxylated agarose composite hydrogels for wound healing. ACS applied materials & interfaces 2016, 8 (42), 28511-28521.
Yan, W.; Shi, M.; Dong, C.; Liu, L.; Gao, C., Applications of tannic acid in membrane technologies: A review. Advances in Colloid and Interface Science 2020, 284, 102267.
Etter, M. C., Encoding and decoding hydrogen-bond patterns of organic compounds. Accounts of Chemical Research 1990, 23 (4), 120-126.
Oh, H. I.; Hoff, J. E.; Armstrong, G. S.; Haff, L. A., Hydrophobic interaction in tannin-protein complexes. Journal of Agricultural and Food Chemistry 1980, 28 (2), 394-398.
Chandler, D., Interfaces and the driving force of hydrophobic assembly. Nature 2005, 437 (7059), 640-647.
Berne, B. J.; Weeks, J. D.; Zhou, R., Dewetting and Hydrophobic Interaction in Physical and Biological Systems. Annual Review of Physical Chemistry 2009, 60 (1), 85-103.
Campinas, M.; Viegas, R. M. C.; Rosa, M. J., Modelling and understanding the competitive adsorption of microcystins and tannic acid. Water Research 2013, 47 (15), 5690-5699.
Erel-Unal, I.; Sukhishvili, S. A., Hydrogen-bonded multilayers of a neutral polymer and a polyphenol. Macromolecules 2008, 41 (11), 3962-3970.
Rahim, M. A.; Ejima, H.; Cho, K. L.; Kempe, K.; Müllner, M.; Best, J. P.; Caruso, F., Coordination-Driven Multistep Assembly of Metal–Polyphenol Films and Capsules. Chemistry of Materials 2014, 26 (4), 1645-1653.
Wang, J.; Zheng, S.; Liu, J.; Xu, Z., Tannic acid adsorption on amino-functionalized magnetic mesoporous silica. Chemical Engineering Journal 2010, 165 (1), 10-16.
Wang, J.; Zheng, C.; Ding, S.; Ma, H.; Ji, Y., Behaviors and mechanisms of tannic acid adsorption on an amino-functionalized magnetic nanoadsorbent. Desalination 2011, 273 (2), 285-291.
Ejima, H.; Richardson, J. J.; Liang, K.; Best, J. P.; van Koeverden, M. P.; Such, G. K.; Cui, J.; Caruso, F., One-Step Assembly of Coordination Complexes for Versatile Film and Particle Engineering. Science 2013, 341 (6142), 154-157.
Kim, B. J.; Han, S.; Lee, K. B.; Choi, I. S., Biphasic supramolecular self‐assembly of ferric ions and tannic acid across interfaces for nanofilm formation. Advanced Materials 2017, 29 (28), 1700784.
Çakar, S.; Özacar, M., The pH dependent tannic acid and Fe-tannic acid complex dye for dye sensitized solar cell applications. Journal of Photochemistry and Photobiology A: Chemistry 2019, 371, 282-291.
Pinnaratip, R.; Bhuiyan, M. S. A.; Meyers, K.; Rajachar, R. M.; Lee, B. P., Multifunctional biomedical adhesives. Advanced healthcare materials 2019, 8 (11), 1801568.
Ambrosi, G.; Formica, M.; Fusi, V.; Giorgi, L.; Micheloni, M., Polynuclear metal complexes of ligands containing phenolic units. Coordination Chemistry Reviews 2008, 252 (10), 1121-1152.
Blesa, M. A.; Weisz, A. D.; Morando, P. J.; Salfity, J. A.; Magaz, G. E.; Regazzoni, A. E., The interaction of metal oxide surfaces with complexing agents dissolved in water. Coordination Chemistry Reviews 2000, 196 (1), 31-63.
Veisi, H.; Moradi, S. B.; Saljooqi, A.; Safarimehr, P., Silver nanoparticle-decorated on tannic acid-modified magnetite nanoparticles (Fe3O4@TA/Ag) for highly active catalytic reduction of 4-nitrophenol, Rhodamine B and Methylene blue. Materials Science and Engineering: C 2019, 100, 445-452.
Deng, G.; Wang, T.; Alshehri, A. A.; Alzahrani, K. A.; Wang, Y.; Ye, H.; Luo, Y.; Sun, X., Improving the electrocatalytic N2 reduction activity of Pd nanoparticles through surface modification. Journal of Materials Chemistry A 2019, 7 (38), 21674-21677.
Ostovari, A.; Hoseinieh, S. M.; Peikari, M.; Shadizadeh, S. R.; Hashemi, S. J., Corrosion inhibition of mild steel in 1M HCl solution by henna extract: A comparative study of the inhibition by henna and its constituents (Lawsone, Gallic acid, α-d-Glucose and Tannic acid). Corrosion Science 2009, 51 (9), 1935-1949.
Khoobi, M.; Delshad, T. M.; Vosooghi, M.; Alipour, M.; Hamadi, H.; Alipour, E.; Hamedani, M. P.; Safaei, Z.; Foroumadi, A.; Shafiee, A., Polyethyleneimine-modified superparamagnetic Fe3O4 nanoparticles: An efficient, reusable and water tolerance nanocatalyst. Journal of Magnetism and Magnetic Materials 2015, 375, 217-226.
Chen, Z.; Lv, Z.; Sun, Y.; Chi, Z.; Qing, G., Recent advancements in polyethyleneimine-based materials and their biomedical, biotechnology, and biomaterial applications. Journal of Materials Chemistry B 2020, 8 (15), 2951-2973.
Lee, A. Y.; Cho, M.-H.; Kim, S., Recent advances in aerosol gene delivery systems using non-viral vectors for lung cancer therapy. Expert opinion on drug delivery 2019, 16 (7), 757-772.
Zhang, M.; Zhang, M.; Wang, J.; Cai, Q.; Zhao, R.; Yu, Y.; Tai, H.; Zhang, X.; Xu, C., Retro-inverso follicle-stimulating hormone peptide-mediated polyethylenimine complexes for targeted ovarian cancer gene therapy. Drug delivery 2018, 25 (1), 995-1003.
Rudolph, C.; Lausier, J.; Naundorf, S.; Müller, R. H.; Rosenecker, J., In vivo gene delivery to the lung using polyethylenimine and fractured polyamidoamine dendrimers. The journal of gene medicine 2000, 2 (4), 269-278.
Satyapal, S.; Filburn, T.; Trela, J.; Strange, J., Performance and properties of a solid amine sorbent for carbon dioxide removal in space life support applications. Energy & Fuels 2001, 15 (2), 250-255.
Lee, H. J.; Lee, S. G.; Oh, E. J.; Chung, H. Y.; Han, S. I.; Kim, E. J.; Seo, S. Y.; Do Ghim, H.; Yeum, J. H.; Choi, J. H., Antimicrobial polyethyleneimine-silver nanoparticles in a stable colloidal dispersion. Colloids and Surfaces B: Biointerfaces 2011, 88 (1), 505-511.
Knowles, K. R.; Hanson, C. C.; Fogel, A. L.; Warhol, B.; Rider, D. A., Layer-by-layer assembled multilayers of polyethylenimine-stabilized platinum nanoparticles and PEDOT: PSS as anodes for the methanol oxidation reaction. ACS Applied Materials & Interfaces 2012, 4 (7), 3575-3583.
Kuo, P.-L.; Chen, W.-F.; Huang, H.-Y.; Chang, I.-C.; Dai, S. A., Stabilizing effect of pseudo-dendritic polyethylenimine on platinum nanoparticles supported on carbon. The Journal of Physical Chemistry B 2006, 110 (7), 3071-3077.
Bali, K.; Bak, M.; Szarka, K.; Juhász, G.; Sáfrán, G.; Pécz, B.; Mihály, J.; Mészáros, R., Controlling the morphology of poly(ethyleneimine)/gold nanoassemblies through the variation of pH and electrolyte additives. Journal of Molecular Liquids 2021, 322, 114559.
Note, C.; Kosmella, S.; Koetz, J., Poly (ethyleneimine) as reducing and stabilizing agent for the formation of gold nanoparticles in w/o microemulsions. Colloids and Surfaces A: Physicochemical and Engineering Aspects 2006, 290 (1-3), 150-156.
Goyal, R.; Tripathi, S.; Tyagi, S.; Sharma, A.; Ram, K. R.; Chowdhuri, D.; Shukla, Y.; Kumar, P.; Gupta, K., Nanomed.: Nanotechnol. Biol. Med 2012, 8, 167.
Wu, S.; Li, G.; Liu, W.; Yu, D.; Li, G.; Liu, X.; Song, Z.; Wang, H.; Liu, H., Fabrication of polyethyleneimine-paper composites with improved tribopositivity for triboelectric nanogenerators. Nano Energy 2022, 93, 106859.
Cao, K.; Zhang, M.; Liu, G., The effect of end group and molecular weight on the yellowness of polyetherimide. Macromolecular rapid communications 2018, 39 (14), 1800045.
Qi, H.; Zhang, L.; Zhang, G.; Wang, T.; Wang, Q., Comparative study of tribochemistry of ultrahigh molecular weight polyethylene, polyphenylene sulfide and polyetherimide in tribo-composites. Journal of colloid and interface science 2018, 514, 615-624.
Zakeri, A.; Kouhbanani, M. A. J.; Beheshtkhoo, N.; Beigi, V.; Mousavi, S. M.; Hashemi, S. A. R.; Karimi Zade, A.; Amani, A. M.; Savardashtaki, A.; Mirzaei, E.; Jahandideh, S.; Movahedpour, A., Polyethylenimine-based nanocarriers in co-delivery of drug and gene: a developing horizon. Nano reviews & experiments 2018, 9 (1), 1488497.
Parize, R.; Garnier, J. D.; Appert, E.; Chaix-Pluchery, O.; Consonni, V., Effects of Polyethylenimine and Its Molecular Weight on the Chemical Bath Deposition of ZnO Nanowires. ACS Omega 2018, 3 (10), 12457-12464.
Liu, M.; Jia, L.; Zhao, Z.; Han, Y.; Li, Y.; Peng, Q.; Zhang, Q., Fast and robust lead (II) removal from water by bioinspired amyloid lysozyme fibrils conjugated with polyethyleneimine (PEI). Chemical Engineering Journal 2020, 124667.
Nandi, S.; Jamatia, R.; Sarkar, R.; Sarkar, F. K.; Alam, S.; Pal, A. K., One‐Pot Multicomponent Reaction: A Highly Versatile Strategy for the Construction of Valuable Nitrogen‐Containing Heterocycles. ChemistrySelect 2022, 7 (33), e202201901.
Dömling, A.; Wang, W.; Wang, K., Chemistry and Biology Of Multicomponent Reactions. Chemical Reviews 2012, 112 (6), 3083-3135.
Slobbe, P.; Ruijter, E.; Orru, R. V. A., Recent applications of multicomponent reactions in medicinal chemistry. MedChemComm 2012, 3 (10), 1189-1218.
Zarganes-Tzitzikas, T.; Dömling, A., Modern multicomponent reactions for better drug syntheses. Organic Chemistry Frontiers 2014, 1 (7), 834-837.
Gomaa, H. A., A comprehensive review of recent advances in the biological activities of quinazolines. Chemical Biology & Drug Design 2022, 100 (5), 639-655.
Wang, D.; Gao, F., Quinazoline derivatives: synthesis and bioactivities. Chemistry Central Journal 2013, 7 (1), 95.
Karan, R.; Agarwal, P.; Sinha, M.; Mahato, N., Recent Advances on Quinazoline Derivatives: A Potential Bioactive Scaffold in Medicinal Chemistry. ChemEngineering 2021, 5 (4), 73.
Asif, M., Chemical characteristics, synthetic methods, and biological potential of quinazoline and quinazolinone derivatives. International journal of medicinal chemistry 2014, 2014.
Wahan, S. K.; Sharma, B.; Chawla, P. A., Medicinal perspective of quinazolinone derivatives: Recent developments and structure–activity relationship studies. Journal of Heterocyclic Chemistry 2022, 59 (2), 239-257.
Hameed, A.; Al-Rashida, M.; Uroos, M.; Ali, S. A.; Arshia; Ishtiaq, M.; Khan, K. M., Quinazoline and quinazolinone as important medicinal scaffolds: a comparative patent review (2011–2016). Expert Opinion on Therapeutic Patents 2018, 28 (4), 281-297.
Tamaddon, F.; Moradi, B.; Nasiri, A. R.; Rahbar, F., Synthesis and in Vitro Evaluation of Antifungal and Antibacterial Activity of 2, 3-dihydroquinazolinone Derivatives. Tolooebehdasht 2018, 17 (3), 77-85.
Wang, M.; Zhang, T. T.; Liang, Y.; Gao, J. J., Efficient synthesis of mono-and disubstituted 2, 3-dihydroquinazolin-4 (1H)-ones using copper benzenesulfonate as a reusable catalyst in aqueous solution. Monatshefte für Chemie-Chemical Monthly 2012, 143 (5), 835-839.
Shaterian, H. R.; Rigi, F., An efficient synthesis of quinazoline and xanthene derivatives using starch sulfate as a biodegradable solid acid catalyst. Research on Chemical Intermediates 2015, 41 (2), 721-738.
Toosi, F. S.; Khakzadi, M., A new and facile synthesis 2, 3-dihydroquinazolin-4 (1H)-ones. Research on Chemical Intermediates 2015, 41 (1), 311-317.
Zhang, Z.-H.; Lü, H.-Y.; Yang, S.-H.; Gao, J.-W., Synthesis of 2, 3-dihydroquinazolin-4 (1 H)-ones by three-component coupling of isatoic anhydride, amines, and aldehydes catalyzed by magnetic Fe3O4 nanoparticles in water. Journal of combinatorial chemistry 2010, 12 (5), 643-646.
Magyar, Á.; Hell, Z., One-Pot Three-Component Synthesis of 2, 3-Dihydroquinazolin-4 (1H)-Ones in the Presence of a Molecular Sieve Supported Lanthanum Catalyst. Catalysis Letters 2016, 146 (6), 1153-1162.
Song, Z.; Liu, L.; Wang, Y.; Sun, X., Efficient synthesis of mono-and disubstituted 2, 3-dihydroquinazolin-4 (1H)-ones using aluminum methanesulfonate as a reusable catalyst. Research on Chemical Intermediates 2012, 38 (3-5), 1091-1099.
Safari, J.; Gandomi-Ravandi, S., Application of the ultrasound in the mild synthesis of substituted 2, 3-dihydroquinazolin-4 (1H)-ones catalyzed by heterogeneous metal–MWCNTs nanocomposites. Journal of Molecular Structure 2014, 1072, 173-178.
Nikooei, N.; Dekamin, M. G.; Valiey, E., Benzene‑1, 3, 5‑tricarboxylic acid‑functionalized MCM‑41 as a novel and recoverable hybrid catalyst for expeditious and efficient synthesis of 2, 3‑dihydroquinazolin‑4 (1H)‑ones via one‑pot three‑component reaction. RESEARCH ON CHEMICAL INTERMEDIATES 2020.
Sahiner, N.; Sagbas, S.; Sahiner, M.; Demirci, S., Degradable tannic acid/polyethyleneimine polyplex particles with highly antioxidant and antimicrobial effects. Polymer Degradation and Stability 2016, 133, 152-161.
Etivand, N.; Khalafy, J.; Dekamin, M. G., Fast and efficient green procedure for the synthesis of Benzo [5, 6] chromene derivatives and their sulfur analogues in water by organocatalyst potassium phthalimide-N-oxyl. Synthesis 2020, 52 (11), 1707-1718.
Keshavarz, M.; Dekamin, M. G.; Mamaghani, M.; Nikpassand, M., Tetramethylguanidine-functionalized melamine as a multifunctional organocatalyst for the expeditious synthesis of 1,2,4-triazoloquinazolinones. Scientific Reports 2021, 11 (1), 14457.
Yoksan, R.; Matsusaki, M.; Akashi, M.; Chirachanchai, S., Controlled hydrophobic/hydrophilic chitosan: colloidal phenomena and nanosphere formation. Colloid and Polymer Science 2004, 282 (4), 337-342.
Wang, M.; Zhang, T.; Gao, J.; Liang, Y., Cation-exchange resin as an efficient hetero-geneous catalyst for one-pot three-component synthesis of 2, 3-dihydro-4 (1H)-quinazolinones. Chemistry of Heterocyclic Compounds 2012, 48 (6), 897-902.
Yale, H. L.; Kalkstein, M., Substituted 2, 3-dihydro-4 (1H)-quinazolinones. A new class of inhibitors of cell multiplication. Journal of medicinal chemistry 1967, 10 (3), 334-336.
Salehi, P.; Dabiri, M.; Zolfigol, M. A.; Baghbanzadeh, M., A novel method for the one-pot three-component synthesis of 2, 3-dihydroquinazolin-4 (1H)-ones. Synlett 2005, 2005 (07), 1155-1157.
Chen, J.; Wu, D.; He, F.; Liu, M.; Wu, H.; Ding, J.; Su, W., Gallium (III) triflate-catalyzed one-pot selective synthesis of 2, 3-dihydroquinazolin-4 (1H)-ones and quinazolin-4 (3H)-ones. Tetrahedron Letters 2008, 49 (23), 3814-3818.

Tables 1 and 2 are available in the Supplementary Files section.

Schemes 1 and 2 are available in the Supplementary Files section.

No competing interests reported.

Scheme1.png
Scheme 1. The structure of TP support.
Scheme2.png
Scheme 2. Mechanism of synthesis of 2,3-dihydroquinazolin-4(1H)-ones.
GraphicalAbstract.png
Table1and2.docx
ElectronicSupplementaryinformation1.docx

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Tannic acid-poly ethyleneimine magnetic nanoparticles: an efficient and recyclable catalyst for green synthesis of 2,3-dihydroquinazole derivatives

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EDX analysis of TP and TPMS nanocatalyst (1)

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