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. 2025 May 12;15:16438. doi: 10.1038/s41598-025-01119-7

Accelerated synthesis of 3-dihydroquinazolin-4(1H)-one derivatives using nano-SiO2-SO3H as an efficient acidic catalyst

Habyl Naeemi 1, Nasrin Shadjou 1,2,✉, Mehdi Mahmoudian 1,2
PMCID: PMC12069535  PMID: 40355459

Abstract

2,3-dihydroquinazolin-4(1H)-one derivatives are recognized as vital compounds in medicinal chemistry due to their diverse biological activities, making them valuable for pharmaceutical research and therapeutic applications. Hence, the rapid and accurate synthesis of these derivatives need efficient nano-catalysts. The study outlines the preparation of nano-SiO2-SO3H through the covalent attachment of sulfonic acid groups to silica nanoparticles. Then, this material is applied as a catalyst for the efficient one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives. The reaction involves isatoic anhydride, an aromatic aldehyde, and ammonium acetate, directed under solvent-free conditions at a temperature of 110 °C. Also, the prepared catalyst characterized using Field Emission Scanning Electron Microscopy (FE-SEM) and Transmission Electron Microscopy (TEM) for morphological analysis, Fourier Transform Infrared Spectroscopy (FT-IR) for functional group identification, and Energy Dispersive X-ray Spectroscopy (EDAX) for its elemental composition. The presence of sulfonic acid groups as a Brønsted acids, enhance the catalytic properties of the silica nanoparticles and facilitate the reaction between the reactants in synthesis process and make the designed catalyst as a suitable candidate for promoting the 2,3-dihydroquinazolin-4(1H)-one synthesis. This synthesis protocol offers a sustainable and eco-friendly approach, eliminating the use of toxic solvents. It provides significant advantages compared to previously reported methods, such as using of nontoxic, green, and stable nanocatalyst. Additionally, the catalyst is easily recoverable and reusable, the reactions proceed under solvent-free conditions, and the process characterized by short reaction times (5–20 min). Furthermore, it achieves excellent yields ranging from 85 to 98% and features a simple workup procedure, making it highly relevant for advancing environmental chemistry practices.

Keywords: Nano-SiO2-SO3H; 2,3-dihydroquinazolin-4(1H)-ones; Solvent free conditions; Nanocatalyst; Advanced nanomaterials

Subject terms: Nanoscience and technology, Nanoscale materials

Introduction

Homogeneous acids are essential in facilitating chemical reactions with industrial applications. However, their application is frequently limited due to their corrosiveness properties and negative environmental impact. To overcome these drawbacks, scientists are investigating the potential of heterogeneous catalysts. These alternatives not only simplify material separation and recycling, but also minimize the amount of catalyst required. As a result, there is increasing focus on developing and refining solid catalysts to address these challenges1–3.

Silica-based materials are valued for being cost-effective, eco-friendly, and thermal stability, which makes them ideal for various applications. These materials, which have multiple hydroxyl (OH) groups on their surface, can be modified with various functional groups. This process improves their chemical and physical properties, making them more suitable for specific applications such as catalysis, adsorption, or biomedical uses4–6. Recent studies have explored the covalent attachment of sulfonic acid as an acidic functional group to mesoporous silica-based materials using grafting and co-condensation methods lead to enhancing of their role in organic synthesis and production of important reagents in medical chemistry7,8.

These functionalized groups are used as efficient heterogeneous catalysts for various organic reactions, including esterification, acylation, and condensation9,10. Among the various functional groups, sulfonic acid acts as a strong Brønsted acid catalyst on silica-based materials and provide better performance compared to traditional catalysts11. These functionalized nano-catalysts have several advantages, such as easy separation, regeneration, and reusability without significant loss of their activity12. Alo, these materials have hydrophobic nature and crystalline pore structure9. Additionally, the functionalized silica-based catalysts demonstrate good hydrothermal stability and can be recovered and reused multiple times, making them attractive for industrial and pharmaceutical applications10,11. For example, sulfonic acid groups functionalized silica (SiO2-Pr-SO3H) and metal-organic frameworks (MOFs) have been successfully applied in various organic synthesis and demonstrated high catalytic activity and reusability13,14. For example, sulfonic acid-functionalized silica-coated magnetic nanoparticles, exhibit high catalytic activity and reusability in synthesizing 2-substituted benzimidazole and bis indole methane derivatives, with effective recovery using an external magnet over six cycles15.

Solvent-free reactions, also known as solid-state or dry-phase reactions, represent an innovative approach in organic chemistry that completely eliminates the use of various solvents16. This technique aligns with the principles of green chemistry by drastically reducing hazardous waste and minimizing environmental impact. In conventional organic synthesis, solvents are often critical but can pose environmental hazards and contribute to pollution. By omitting solvents, chemists can adopt more sustainable methods while enhancing the efficiency of synthetic processes. Consequently, solvent-free reactions have become increasingly popular in modern organic chemistry17. Typically, various methods such as grinding, using of ultrasonic waves, and microwaves are employed to carry out reactions under solvent-free conditions. Grinding of the reactants under solvent-free conditions can lead to effective mixing and increased reaction yield18.

2,3-dihydroquinazolin-4(1H)-one derivatives are recognized as crucial compounds in medicinal chemistry due to their diverse biological activities, making them valuable for pharmaceutical research and therapeutic applications. These nitrogen-containing heterocyclic compounds, demonstrates notable pharmacological properties, including anticancer, antimicrobial, and anti-inflammatory effects19,20. The flexibility of quinazoline-based compounds is evident in their potential applications in treating various diseases, such as diabetes, viral infections, and oxidative stress-related conditions. Also, their importance in drug discovery is further emphasized by the presence of quinazoline/quinazolinone moieties in several marketed drugs. The ease of synthetic accessibility and flexibility in structural modifications make these compounds particularly attractive for medicinal chemists21.

Recently, various catalysts such as heteropoly acids22, ZnCl223, [C12Py][FeCl3Br] ionic liquid24, and InBr325 have been applied for the synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives under various experimental conditions,. Although these catalysts and methods have some advantages, most of them suffer from one or more limitation such as difficulty in preparation, recovery and reusability of the catalyst, low yields, long reaction times and using of toxic solvents.

Following our previous studies in the synthesis and design of green and eco-friendly catalysts26,27, this study focuses on the preparation of nano-SiO2-SO3H, for the one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-ones. The process involves the reaction of isatoic anhydride, aromatic aldehydes, and ammonium acetate under solvent-free conditions. This nano-catalyst with high surface area and a lot of acidic active sites, facilitates strong interactions between the reactants and allowing the reaction to proceed under milder reaction conditions and shorter reaction times. In addition, this catalyst can be easily recovered and reused several times and retains its catalytic activity with only a minimal decrease in its efficiency, presenting a cost-efficient and environmentally friendly alternative (Scheme 1).

Scheme 1.

Scheme 1

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Synthesis of 2,3-dihydroquinazolin-4(1H)-ones in the presence of nano-SiO2-SO3H as a catalyst under solvent free conditions.

Experimental

Materials

Nano-SiO2, ClSO3H, isatoic anhydride, aromatic aldehyde, ammonium acetate, n-Hexane, EtOH, and ZnO were purchased from Sigma. All the mentioned materials were utilized in their original state without undergoing additional purifications.

Instruments

FTIR spectroscopy was applied to investigate the functional groups of nanostructures and synthesis compounds over a scanned range of 400 to 4000 cm−1 using a WQF-510 A spectrophotometer. The shape and morphology of the membranes were examined using FESEM (HITACHI S-4160) and TEM (Philips BioTwin, the Netherlands), while EDAX was applied to exhibit the alteration and distribution of particles in the prepared nano-catalyst.

Preparation of the catalyst

The preparation of the silica-based nano-catalyst (nano-SiO2-SO3H) involved functionalizing nano-silica particles with sulfonic acid groups to enhance their acidic sites and catalytic activity. 60 g of silica nanoparticles were functionalized via a reaction involving 0.7 mol (81.13 g) of chloro-sulfonic acid (ClSO3H). The procedure was conducted in a 50 mL suction flask equipped with a constant-pressure dropping funnel. The ClSO3H was added dropwise at room temperature over a period of 30 min. A gas tube was used to direct the emitted hydrochloride gas into an adsorption solution. After the modification process was complete, the mixture was stirred for an additional 30 min, resulting in the formation of a white solid product, nano-SiO2-SO3H (Scheme 2).

Scheme 2.

Scheme 2

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Modification of nano-SiO2 with sulfonic acid groups.

General procedure for the synthesis of 2,3-dihydroquinazolin-4(1H)-one’s derivatives

In a test tube, a mixture of isatoic anhydride (0.5 mmol, 0.08 g), aromatic aldehyde (0.5 mmol), ammonium acetate (1 mmol, 0.077 g), and nano-SiO2-SO3H (0.02 g) was stirred at 110 °C for an appropriate period of time. The reaction progress was monitored through TLC paper utilizing in a mixture of ethyl acetate and n-hexane (1:1). Once the reaction completed, hot ethanol was added to the mixture, and the catalyst was separated through filtration. The pure final products were then isolated by recrystallizing in ethanol.

Results and conditions

Characterization of the prepared nano-catalyst

The prepared catalyst characterized using FT-IR, FE-SEM, TEM and EDAX techniques. The FT-IR spectra of nano-SiO2-SO3H is shown in Fig. 1. The peaks in 809 cm−1 and 1105 cm−1 are related to the symmetric and unsymmetric vibrations of Si-O-Si and S-O bonds, respectively. The band in 470 cm−1 is belong to the bending frequency of Si-O-Si bonds. The broadband peak in 3419 cm−1 belongs to O-H stretching frequency of silanol groups and SO3H moiety in the surface of prepared catalyst. Also, the peak observed at 1628 cm−¹ corresponds to the H-O-H bending vibration, which is characteristic of both free and adsorbed water molecules.

Fig. 1.

Fig. 1

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FT-IR spectra of prepared nano-SiO2-SO3H.

The FE-SEM images typically reveal the surface morphology and particle size distribution of the nano-SiO2-SO3H. These images show that the silica nanoparticles are uniformly distributed, with a relatively small size, which is essential for their application in catalysis and other fields. The presence of the -SO3H functional group on the silica surface enhances the material’s catalytic properties, making it suitable for various chemical reactions. The images often depict a rough surface texture, indicating a high surface area that is beneficial for catalytic activity and adsorption processes (Fig. 2).

Fig. 2.

Fig. 2

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FE-SEM images of prepared nano-SiO2-SO3H.

The TEM images of prepared nano-SiO2-SO3H are presented in Fig. 3, providing a detailed visualization of the material’s morphology and structural characteristics. The images show that nano-SiO2-SO3H particles exhibit a uniform size distribution, less than 100 nm in diameter.

Fig. 3.

Fig. 3

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TEM images of nano-SiO2-SO3H.

Also, EDAX analysis of nano-SiO2-SO3H is shown in Fig. 4. The presence of Si, O, and S confirm the successful modification of nano-SiO2 with SO3H functional groups.

Fig. 4.

Fig. 4

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EDAX analysis of nano-SiO2-SO3H.

The acidity of the prepared catalyst was determined using two methods. First, the pH of catalyst using litmus paper was approximately 2. Secondly, titration with 0.01 M sodium hydroxide revealed that 0.05 g of the catalyst corresponded to 0.0185 moles of H+ (Fig. 5).

Fig. 5.

Fig. 5

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Titration of the catalyst with sodium hydroxide.

Optimization of the reaction condition

At first, the reaction conditions were optimized using a mixture of isatoic anhydride (0.5 mmol, 0.08 g), 4-chlorobenzaldehyde (0.5 mmol, 0.07 g), and ammonium acetate (1 mmol, 0.077 g), under various parameters. Then, 0.02 g of different catalysts, such as Fe2O3-MCM-41-SO3H, ZnO, KCC-1/ZnO, and nano-SiO2-SO3H were employed for the model reaction in ethanol and under solvent-free conditions at temperatures of 70 °C and 110 °C (Scheme 3).

Scheme 3.

Scheme 3

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A model reaction for optimization of the reaction conditions.

Initially, the reaction conducted without a catalyst at 120 °C, under solvent-free conditions resulted in an 80% yield within 30 min (entry 1, Table 1)28. The synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives has traditionally depended on the use of various types of Lewis acids and acidic catalysts. Considering this, the effectiveness of ZnO nanoparticles (0.02 g) was evaluated in combination with a eutectic solvent in a model reaction. Findings revealed that at 70 °C, the reaction achieved a 35% yield after 65 min (entry 2). In contrast, employing ZnO nanoparticles (0.02 g) under solvent-free conditions at 110 °C allowed the reaction to be completed in just 10 min with excellent yield (98%), highlighting a remarkable improvement in both efficiency and reaction time (entry 3). Also, ZnO particles were embedded within dendritic fibrous nano silica (KCC-1) to enhance their recovery and reusability. These modified particles were subsequently employed as a catalyst for the solvent-free synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives at 70 °C and 110 °C. Nevertheless, the results were not satisfactory at all (entries 4 and 5), possibly due to insufficient preparation of the catalytic substrate. Alos, Fe2O3-MCM-41-SO3H (0.02 g) was tested for the model reaction which the excellent yield (95%) was obtained in 15 min (entry 6).

Table 1.

Optimization of reaction conditions using various catalysis.

Entry Solvent Catalyst Time (min) Yield (%)
1 Solvent free, 120 °C - 30 8028
2 ChCl: EG, 70 °C ZnO 65 35
3 Solvent free, 110 °C ZnO 10 98
4 Solvent free, 70 °C KCC-1/ZnO 20 Trace
5 Solvent free, 110 °C KCC-1/ZnO 30 Trace
6 Solvent free, 110 °C Fe2O3-MCM-41-SO3H 15 95
7 Ethanol, reflux Nano-SiO2-SO3H 90 60
8 Solvent free, 110 °C Nano-SiO2-SO3H (0.02 g) 8 98
9 Solvent free, 110 °C Nano-SiO2-SO3H (0.03 g) 8 98
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The acidic characteristics of silica nanoparticles, as well as their easy preparation, recyclability and sustainability, were demonstrated by evaluating the performance of nano-SiO2-SO3H (0.02 g) in a model reaction conducted under reflux in ethanol (entry 7). However, the reaction was incomplete after 90 min, yielding only 60% of the desired product. The study demonstrated that performing the reaction under solvent-free conditions at 110 °C provided the most favorable results (entry 8). Optimization of catalyst quantity revealed that 0.02 g of nano-SiO2-SO3H was the most effective, producing the highest yield (98%) in the shortest time (8 min). Increasing the amount of catalyst beyond this did not improve the reaction yield (entry 9). This catalyst proves to be a more economical, safer, and recyclable option compared to other commonly used acidic catalysts.

The research highlights an efficient method for the synthesizing 2,3-dihydroquinazolin-4(1H)-one derivatives by employing aromatic compounds with diverse substituents, encompassing both electron-donating and electron-withdrawing groups. This technique sets itself apart by providing higher product yields and significantly reducing reaction times compared to previous approaches (Table 2).

Table 2.

Synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives using nano-SiO2-SO3H under solvent free conditions.

Entry Product Time (min) Yield (%) m. p. (°C) found m. p. (°C) reported Ref.
1 graphic file with name 41598_2025_1119_Figa_HTML.gif 8 98 203–205 203–206 29
2 graphic file with name 41598_2025_1119_Figb_HTML.gif 10 85 200–202 195–198 29
3 graphic file with name 41598_2025_1119_Figc_HTML.gif 10 94 178–180 180–183 29
4 graphic file with name 41598_2025_1119_Figd_HTML.gif 8 96 216–218 219–221 29
5 graphic file with name 41598_2025_1119_Fige_HTML.gif 20 95 186–188 186–188 30
6 graphic file with name 41598_2025_1119_Figf_HTML.gif 20 92 204–205 205–208 29
7 graphic file with name 41598_2025_1119_Figg_HTML.gif 20 95 186–188 186–188 29
8 graphic file with name 41598_2025_1119_Figh_HTML.gif 5 92 230–231 231–232 31
9 graphic file with name 41598_2025_1119_Figi_HTML.gif 10 95 210–212 210–212 29
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The proposed mechanism is shown in the Scheme 4. The synthesis process in the presence of nano-catalyst involves a three-component coupling reaction. Initially, isatoic anhydride which activated with nano-SiO2-SO3H, reacts with ammonium acetate and this reaction leads to the formation of an intermediate (2-aminobenzamide), which then reacts with aromatic aldehyde and undergoes cyclization to produce the 2,3-dihydroquinazolin-4(1H)-one compounds under solvent-free conditions. The nano-SiO2-SO3H catalyst not only enhances the reaction rate by activation of the reactants, but also offers the advantage of being easily recoverable and reusable, promoting a more sustainable and efficient approach.

Scheme 4.

Scheme 4

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Proposed mechanism for the synthesis of 2,3-dihydroquinazolin-4(1H)-one compounds.

The study highlights the advantages of the nano-SiO2-SO3H catalyst over other reported methods in the literature. Its high surface area and abundance of acidic sites enable more efficient interactions with reactants, leading to improved yields and shorter reaction times. Additionally, the catalyst is easy to prepare, recyclable, and can be reused multiple times with negligible loss in performance. These features make it both cost-effective and environmentally friendly. Its characteristics align seamlessly with the core tenets of sustainable chemistry, demonstrating its practicality, efficiency, and reduced environmental footprint compared to traditional methods (Table 3).

Table 3.

Comparison of the performance of prepared nanocatalyst in the present work with other catalysts in other reported methods.

Entry Catalyst Conditions Time (min) Yield (%) Reference
1 Cellulose-SO3H CH3CN, r.t. 55 90 32
2 ZrCl4 EtOH, r.t. 37 91 33
3 ZnFe2O4@SiO2-ascorbic acid EtOH, reflux 45 95 34
4 lactic acid Solvent free, 70 °C 30 90 35
5 SBA-16/GPTMS-TSC-CuI Solvent free, 60 °C 35 95 36
6 Amberlyst-15 CH3CN, 80 °C 60 85 37
7 Br3-TBA‐Fe3O4 H2O, 70 °C 40 97 38
8 Cerium (IV) sulfate Solvent free, 120 °C 50 90 39
9 nano-SiO2-SO3H Solvent free, 110 °C 8 98 This work
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Reusability of the catalyst

The recoverability and reusability of the catalyst is one of the important properties of the catalyst40. The study explored the reusability of the catalyst in a reaction involving isatoic anhydride (0.5 mmol), aromatic aldehyde (0.5 mmol), and ammonium acetate (1 mmol) under optimized conditions. Upon completing the reaction, the catalyst was efficiently recovered from the mixture, washed with ethanol, and reused over five consecutive cycles without significant reduction in catalytic performance (Fig. 6).

Fig. 6.

Fig. 6

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Reusability of the nano-SiO2-SO3H catalyst for the synthesis of 2,3-dihydroquinazolin-4(1H)-ones derivatives.

Conclusion

In conclusion, synthesis of 2,3-dihydroquinazolin-4(1H)-ones can be efficiently achieved using nano-SiO2-SO3H as a catalyst under solvent-free conditions. This approach offers several advantages, including environmental friendliness, reduced waste, and cost-effectiveness. The use of nano-SiO2-SO3H enhances the reaction’s efficiency due to its high surface area and strong acidic properties, facilitating the formation of the desired product in a shorter time (5–20 min), with higher yields (85–98%). Additionally, conducting the reaction under solvent-free conditions aligns with green chemistry principles, minimizing the use of hazardous solvents and reducing the overall environmental impact. This method is particularly valuable for researchers and industries focused on sustainable and efficient chemical processes.

Acknowledgements

We gratefully acknowledge the support of this work by Urmia University.

Author contributions

Conceptualization: Nasrin ShadjouData curation: Habyl NaeemiFormal Analysis: Nasrin Shadjou and Mehdi Mahmoudian Investigation: Habyl NaeemiMethodology: Nasrin Shadjou and Mehdi MahmoudianProject administration: Nasrin ShadjouSupervision: Nasrin ShadjouValidation: Nasrin Shadjou and Mehdi Mahmoudian Writing – original draft: Habyl Naeemi, Nasrin Shadjou, and Mehdi Mahmoudian Writing – review & editing: Habyl Naeemi, Nasrin Shadjou, and Mehdi Mahmoudian.

Data availability

Access to the data used in this study is available upon request and may be subject to approval by the data provider. Restrictions may apply to the availability of these data, which were used under license for this study. Interested parties are encouraged to contact the corresponding author for further information on accessing the data. All relevant data supporting the findings of this study are available within the article and its supplementary information files, or from the corresponding author upon reasonable request. Access to some data may be restricted due to privacy or ethical restrictions. Any restrictions to data availability will be disclosed at the time of data request.

Declarations

Competing interests

The authors declare no competing interests.

Footnotes

Publisher’s note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

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Data Availability Statement

Access to the data used in this study is available upon request and may be subject to approval by the data provider. Restrictions may apply to the availability of these data, which were used under license for this study. Interested parties are encouraged to contact the corresponding author for further information on accessing the data. All relevant data supporting the findings of this study are available within the article and its supplementary information files, or from the corresponding author upon reasonable request. Access to some data may be restricted due to privacy or ethical restrictions. Any restrictions to data availability will be disclosed at the time of data request.

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