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18 November 2022

Graphitic Carbon Nitride-Supported L-Arginine: Synthesis, Charachterization, and Catalytic Activity in Multi-Component Reactions †

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Catalysts and Organic Synthesis Research Laboratory, Department of Chemistry, Iran University of Science and Technology, Tehran 16846-13114, Iran
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Author to whom correspondence should be addressed.
†
Presented at the 26th International Electronic Conference on Synthetic Organic Chemistry, 15–30 November 2022; Available online: https://ecsoc-26.sciforum.net/.
Chem. Proc.2022, 12(1), 50;https://doi.org/10.3390/ecsoc-26-13708
This article belongs to the Proceedings The 26th International Electronic Conference on Synthetic Organic Chemistry
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Abstract

Graphitic carbon nitride-supported L-arginine (g-C3N4@L-arginine) has been prepared as a heterogeneous catalyst for synthesizing heterocyclic compounds such as pyranopyrazole and acridinedione derivatives. High efficiency, short reaction time, and easy separation are significant features that are reasons for using g-C3N4@L-arginine as a catalyst in one-pot multicomponent reactions. Synthesized nanocatalyst was detected by numerous analyses, such as FE-SEM (Field Emission Scanning Electron Microscopy), EDX (Energy Dispersive X-ray spectroscopy), XRD (X-Ray Diffraction analysis), TGA (Thermo Gravimetric Analysis), and FT-IR (Fourier Transform Infrared Spectroscopy). G-C3N4@L-arginine nanocatalyst was reused 5 times in the reaction with no apparent decrease in reaction yield, which shows acceptable recyclability.

1. Introduction

In the last decades, heterogeneous catalysts have been noticed because of large-scale production and selective product formation [1,2]. G-C3N4 is a widely used support for catalytic entities due to high physical and thermal stability, low density, versatile performance, and recyclability. Moreover, the preparation of g-C3N4 is mostly performed by Cyanamid, urea, dicyanamide, melamine, and thiourea as the precursor [3]. To increase the efficiency of the catalytic performance of g-C3N4 in organic reactions, it is suggested to modify it with organic compounds [4,5,6,7,8].
Significantly, L-arginine is a semi-essential amino acid in living organisms [9], while the guanidine group in L-arginine is the precursor for synthesizing nitrogen derivatives. Using L-arginine with g-C3N4 as a catalyst support can decrease the cost and toxicity. Among other benefits of composite productions with L-arginine, it should be mentioned that making composite with this amino acid can increase thermal stability and molar heat capacities. Although, on the other hand, it can reduce the thermal expansion coefficient. Moreover, the utilization of composites is one of the best ways for synthesizing heterocyclic compounds [10,11,12,13], while heterocyclic compounds have been considered essential groups of organic materials. In addition, they have biological activities which could be effective in the treatment of different diseases. What makes these compounds more important than others is their application in various fields such as medicines, veterinary products, disinfectants, and antioxidants. There are several ways of synthesizing heterocyclic compounds including the multi-stages and one-pot multicomponent reactions. Lately, projects indicate that multicomponent reactions could be the best way for preparing heterocyclic compounds.
Multicomponent reactions have been mostly used for producing heterocyclic compounds because of their advantages including step efficiency, atom economy, and reducing the waste production [14,15,16,17,18]. Pyranopyrazoles are nitrogen-containing heterocyclic compounds with various properties such as anti-cancer, anti-inflammatory, anti-bacterial, antioxidant, and antihypertensive. Knoevenagel condensation, Micheal addition, and cyclization are the main procedures for making pyranopyrazoles derivatives. Various catalysts can be utilized to prepare pyranopyrazole and its derivatives by multicomponent reactions such as cetyltrimethylammonium chloride (CTACl), montmorillonite K10, agave leaf ash, cytosine@MCM-41, Et3N, and PTSA [19,20,21,22,23,24].
Other heterocyclic compounds with biological activities that can be produced with multicomponent reactions are Acridinedione derivatives [25]. They are nitrogen-mediated heterocyclic compounds with a vast spectrum of pharmaceutical and biological activities, namely anti-tumor, SIRT1 inhibitors, anticancer, and antimicrobial agents [26,27,28,29]. There are different precursors such as heterogeneous catalysts for preparing acridinedione, including f-MWCNT, Amberlyst -15, CTAB, and Proline [30,31,32,33]. Usually, recent methods can cover problems of the latest projects such as harsh conditions, long reaction time, and using toxic solvents. Therefore, new methods for synthesizing pyranopyrazole and acridinedione derivatives are a critical challenge in chemistry society. Consequently, in this research, we have synthesized g-C3N4@L-arginine nanocomposite and applied it as a catalyst in the synthesizing pyranopyrazole and acridinedione derivatives in a high yield. The schematic of g-C3N4@L-arginine is shown in Scheme 1.
Scheme 1. Schematic of g-C3N4@L-arginine.

2. Experimental

2.1. Materials

All chemicals were obtained from Sigma–Aldrich and Merck companies. Many analyses have been performed, including Fourier Transform Infrared Spectroscopy (FT-IR), which was recorded by Tensor27 for detecting functional groups of products; Thermal Gravimetric Analysis (TGA) under argon atmosphere was taken by STA 504, which displayed the thermal stability of nanocatalyst; Nuclear Magnetic Resonance (NMR) with Varian-Inova 500 MHz, X-Ray Powder Diffraction (XRD) was performed by Dron-8; Energy-Dispersive X-ray (EDX) Numerix DXP–X10P was employed for indicating the existence of elements of synthesized nanocatalyst; and Field Emission Scanning Electron Microscopy (FE-SEM) with TESCAN-MIRA lll was used for displaying the morphology of synthesized nanocatalyst.

2.2. Preparation of Bulk C3N4 and g-C3N4

Melamine is precursor for preparing bulk carbon nitride, which was heated to 550 °C temperature by the ramp of 2.5 °C.min−1 in a furnace for 4 h. Eventually, a yellow powder was formed. Then, for preparing g-C3N4, 1.0 g bulk C3N4 was stirred with 20 mL H2SO4 at 90 °C for 5 h. Afterward, the mixture was diluted with 200 mL ethanol and stirred at room temperature for 2 h. Then, the mixture was dispersed in 100 mL water/isopropanol (1:1), sonicated for 6 h, and centrifuged to obtain g-C3N4.

2.3. Preparation of g-C3N4@L-Arginine

A total of (1.0 g) g-C3N4 with (20.0 mL) dry toluene was dispersed. Then, (2.0 mL) 1,3-dibromopropane was poured into the final mixture and refluxed for 24 h under an N2 atmosphere. After filtration and washing with ethyl acetate, the product was dried at room temperature. The final product was dissolved in a mixture of water and methanol (1:1). Then, each of the following ingredients was added, respectively: L-arginine (1 mmol), K2CO3 (1.0 mmol), and NaI (1.0 mmol)). Afterward, it was stirred for 24 h at room temperature, washed with water and methanol, then dried at 80 °C.

2.4. Synthesizing Acridinedione Derivatives

A mixture of dimedone (2 mmol), ammonium acetate (1 mmol), aromatic aldehyde (1 mmol), ethanol (5 mL), and catalyst (0.18 mol %) was poured into a flask and refluxed for the appropriate time. The reaction progress was monitored by TLC. After completion of the reaction, the mixture was cooled to room temperature, the catalyst was filtered, and the intended product was obtained by crystallization.

2.5. Synthesizing Pyranopyrazole Derivatives

A mixture of aldehyde (1.0 mmol), ethyl acetoacetate (1.0 mmol), hydrazine hydrate (1.0 mmol), malononitrile (1.0 mmol), catalyst (0.18 mol %), and ethanol (2.0 mL) was poured into a 25 mL round bottom flask and refluxed for the appropriate time. The reaction progress was monitored by TLC. After completion of the reaction, the mixture was cooled to room temperature, the catalyst was filtered, and the intended product was obtained by crystallization.

3. Results and Discussion

FT-IR spectra of a) g-C3N4, b) modified g-C3N4, and c) g-C3N4@L-arginine are shown in Figure 1. In Figure 1a, there is a broad peak around 3000–3300 cm−1 for N-H group stretching vibrations which is related to H- bonding or actually the existence of the OH group of water adsorption by g-C3N4 nanosheets. Figure 1b demonstrates the modified g-C3N4 nanosheets around 3000–2800 cm−1 which is related to C-H stretching vibrations. In Figure 1c, stretching vibrations of C=O and C-O were shown at (1705 cm−1) and (1320–1210 cm−1), respectively. A peak around 1602 cm−1 indicates carbon double bond nitrogen and its stretching vibrations. Values of 1303 and 1082 cm−1 are related to the C-N bond stretching vibrations which are formed from triazine and N-H groups. The C-N stretching vibrations in the ring are significantly revealed at 1448 and 1379 cm−1. A value of 786 cm−1 was shown because of tri-s-triazine vibrations. According to the mentioned peaks, g-C3N4@L-arginine was synthesized [3,4].
Figure 1. FT-IR spectra of (a) g-C3N4, (b) modified g-C3N4, and (c) g-C3N4@L-arginine.
EDX analysis determined the presence of elements in (a) g-C3N4 nanosheets, (b) modified g-C3N4, and (c) g-C3N4@L-arginine. Nitrogen and Carbon elements in nanosheet g-C3N4 are visible in Figure 2a. In Figure 2b, the existence of the Br element would confirm the modification of g-C3N4 nanosheets. Moreover, Figure 2c revealed the presence of carbon, nitrogen, and oxygen, which confirm the synthesizing of g-C3N4@L-arginine.
Figure 2. EDX spectra of (a) g-C3N4 nanosheets, (b) modified g-C3N4, and (c) g-C3N4@L-arginine.
The morphology of g-C3N4@L-arginine nanocatalyst was studied by FE-SEM analysis in two scales (200 nm and 1 μ m). Graphitic and nanosheet properties of C3N4 are apparent based on Figure 3. It can be concluded that the g-C3N4@L-arginine nanocatalyst synthesizing has been successfully performed by observing the g-C3N4 surface roughness.
Figure 3. FE-SEM images of g-C3N4@L-arginine.
The XRD of g-C3N4 nanosheets and g-C3N4@L-arginine have been shown in Figure 4a,b. XRD pattern of nanosheet g-C3N4 in part (a) indicates the diffraction angles of 2θ = 15.96° and 2θ = 27.69°, which approve the synthesizing of g-C3N4 [34]. Diffraction angles of 2θ = 30.97°, 23.60°, 12.21°, 10.85°, 6.07° in XRD pasttern part (b) indicate the L-arginine on the surface of g-C3N4@L-arginine (JCPDS card no. 00–004-0180).
Figure 4. XRD spectra of (a) g-C3N4 nanosheets and (b) g-C3N4@L-arginine.
In Figure 5, g-C3N4@L-arginine thermal stability was shown at the range from 50 to 800 °C. The weight ratio has decreased gradually from 100 to 200 °C because of the removal of absorbed water from g-C3N4@L-arginine. L-arginine’s separation was observed from 200 to 400 °C. There is a dramatic decrease from 400 to 700 °C which is related to g-C3N4 nanosheet decomposition.
Figure 5. TGA spectrum of g-C3N4@L-arginine.

3.1. Application

The catalytic activity of produced heterogeneous nanocatalyst g-C3N4@L-arginine was studied for multi-component reactions. The optimum reaction conditions for synthesizing acridinedione and pyranopyrazole derivatives were evaluated. The synthesis of acridinedione derivatives was performed by using dimedone (2 mmol), 4-chloro benzaldehyde (1 mmol), ammonium acetate (1 mmol), ethanol (5 mL), and catalyst (0.18 mol %) (model reaction 1). In addition, pyranopyrazole derivatives were produced by malononitrile (1.0 mmol), 4-chloro benzaldehyde (1.0 mmol), hydrazine hydrate (1.0 mmol), ethyl acetoacetate (1.0 mmol), ethanol (2.0 mL), and catalyst (0.18 mol %) (model reaction 2). The possibility of aldol reaction in aliphatic aldehydes would be the significant reason for using aromatic aldehydes compared to aliphatic aldehydes. Moreover, the reaction has been monitored by thin-layer chromatography (TLC). The model reactions have been investigated under different and convertible conditions. Initially, the reaction was performed with no catalyst at two different temperatures and the same reaction time (20 min). There was no acceptable efficiency as expected for both reactions (Table 1, entries 1–2). After using the catalyst (Table 1, entries 3–4), the desired products were produced in very small quantities at two different temperatures with the same environmental solvent. By using the catalyst at 80 °C for 20 min, there was a significant yield and efficiency of up to 92% for the first reaction and 91% for the second one (Table 1, entry 5). Moreover, despite increasing the reaction time up to 30 min, no noteworthy changes in the efficiency were observed (Table 1, entry 6).
Table 1. Optimization of g-C3N4@L-arginine for reaction 1 and 2.
In addition, changing the used solvent to water with the same condition as Table 1- entry 5 can decrease the efficiency of reactions 1 and 2 to 65% and 68%, respectively (Table 1, entry 7). If the solvent of the reactions changed to methanol and acetonitrile (Table 1, entries 8 and 9), the reaction yield, in comparison with entry 5, will be increased and decreased, respectively. Likewise, the model reactions were performed by g-C3N4 (0.18 mol %) and L-arginine (0.18 mol %) with the same conditions, while the yield of the final products was decreased.
After optimization, different aromatic aldehydes were used to show the merits of g-C3N4@L-arginine catalytic activity and different pyranopyrazole and acridinedione derivatives were synthesized (Table 2 and Table 3).
Table 2. Synthesis acridinedione derivatives by g-C3N4@L-arginine (a,b).
Table 3. Synthesis pyranopyrazole derivatives by g-C3N4@L-arginine (a,b).

3.2. Mechanism of Using Nanocatalyst for Synthesizing Pyranopyrazole and Acridinedione Derivatives

3.2.1. Pyranopyrazoles

The study of the mechanism for pyranopyrazole derivatives and the proposed mechanism is shown in Scheme 2. In addition, g-C3N4@L-arginine is needed for activating different intermediates and reactants. Malononitrile (I) and aromatic aldehyde (II) would react with each other by the carbon as a nucleophile. Then, it would reacts with the carbonyl group by releasing water and produce intermediate (III). Simultaneously, ethyl acetoacetate (IV) and hydrazine hydrate (V) react with each other and form the intermediate (VI). Afterward, the amine group’s non-bonding electron pair reacts with the ethyl acetoacetate’s carbonyl group. In the following step, the 5-member ring was closed by removing the water molecule. In the last step, two produced intermediates, ((III) and (VI)), would react with each other, and the pryranopyrazole derivative was synthesized.
Scheme 2. Proposed mechanism for synthesizing pyranopyrazole derivatives.

3.2.2. Acridinediones

The study of the mechanism for acridinedione derivative synthesis and the proposed mechanism is exhibited in Scheme 3. For activating the carbonyl group of aldehydes, the presence of g-C3N4 @L-arginine is essential. After activating the carbonyl group with nanocatalyst (I) and producing the hydroxyl group on dimedone (II), the carbon nucleophile would react with activated aromatic aldehyde. Then, the other dimedone reacts with the double bond for donating electrons (III), and after a water molecule removal, the ring is closed by an intramolecular reaction (IV, V and VI). Eventually, the intended product is obtained (VII).
Scheme 3. Proposed mechanism for synthesizing acridinedione derivatives.

3.3. Reusability

The recovery and recyclability of the catalyst are the essential principles of green chemistry. Therefore, the reusability of g-C3N4@L-arginine was studied for synthesizing pyranopyrazole and acridinedione derivatives. G-C3N4@L-arginine was extracted from the reaction, washed with water and ethanol, then dried at 70 °C. It was repeated 5 times in the same conditions. After each reaction, the yield decreased gradually, but it was acceptable (Figure 6).
Figure 6. Reusability of g-C3N4@L-arginine in acridinedione and pyranopyrazole derivatives.

4. Conclusions

In conclusion, in this project, we utilized an easy and convenient method for preparing g-C3N4@L-arginine nanocatalyst and applied it for producing pyranopyrazole and acridinedione derivatives. G-C3N4@L-arginine nanocatalyst has remarkable advantages such as reusability, easy separation, high efficiency, and short reaction time. According to the results, produced nanocatalyst is the superior compared to other reported catalysts.

Author Contributions

Conceptualization, supervision, validation, H.G.; investigation, Z.T.; methodology, P.H., M.T. and Z.T.; writing—review and editing, writing—original draft preparation, H.G., P.H. and F.B. All authors have read and agreed to the published version of the manuscript.

Funding

This research received no external funding.

Institutional Review Board Statement

Not applicable.

Data Availability Statement

Not applicable.

Conflicts of Interest

The authors declare no conflict of interest.

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