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An efficient and green synthesis of 2-phenylquinazolin-4(3H)-ones via t-BuONa-mediated oxidative condensation of 2-aminobenzamides and benzyl alcohols under solvent- and transition metal-free conditions

  • Vy T. B. Nguyen , Dat P. Tran , Tung T. Nguyen , Khoa D. Nguyen EMAIL logo and Ha V. Le EMAIL logo
Published/Copyright: May 23, 2023
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Green Processing and Synthesis
From the journal Green Processing and Synthesis Volume 12 Issue 1

Abstract

Quinazolinone synthesis usually requires employing sensitive substrates, hazardous solvents, large excess oxidants, and expensive catalysts. In this study, an efficient and environmentally benign pathway was developed to synthesize 2-phenylquinazolin-4(3H)-one via oxidative coupling between commercially available and stable chemicals, including 2-aminobenzamide and benzyl alcohol without toxic oxidizing agents and transition-metal catalysts. A high yield of the desired product (up to 84%) was obtained at 120°C for 24 h in the presence of oxygen as a green oxidant and t-BuONa as a base. Importantly, the study scope was expanded toward successfully producing various 2-phenylquinazolin-4(3H)-one derivatives in moderate-to-good yields. Furthermore, control experiments proposed that the conversion involved the initial partial oxidation of benzyl alcohol to the benzaldehyde intermediate under basic conditions, followed by the condensation, intramolecular nucleophilic addition, and oxidative dehydrogenation to 2-phenylquinazolin-4(3H)-one.

Keywords: 2-phenylquinazolin-4(3H)-one; benzyl alcohol; green conditions; oxidative coupling

1 Introduction

Quinazolinone derivatives, one of the important classes of six-membered nitrogen-containing heterocyclic skeletons, have attracted much attention due to their broad application scope in chemistry and pharmaceutics [1,2,3,4,5,6,7]. Biologically crucial molecules involving the quinazolinone core occurred naturally in various classes of plants, microorganisms, and animals [8,9,10,11,12,13,14,15]. In particular, numerous 4(3H)-quinazolinone-based compounds have been commonly explored in medicinal chemistry with noteworthy pharmacological activities such as anticonvulsant, anticancer, anti-inflammatory, antimicrobial, anti-HIV, antiviral, and antidiabetic properties and inhibitory effects on poly-(ADP-ribose) polymerase, thymidylate synthase, and tyrosine kinase (Figure 1) [16,17,18,19,20,21,22,23,24,25,26,27,28,29,30,31,32,33]. Therefore, many efforts have been made to investigate new efficient and facile approaches toward constructing 4(3H)-quinazolinones. The traditional route to obtain 4(3H)-quinazolinones could be based on three-component condensation involving carboxylic acid, amine, and 2-aminobenzoic acid or the cascade condensation/oxidation sequence of aldehydes with 2-aminobenzonitrile, promoted by acid or base [34,35,36,37,38]. These approaches are indeed highly efficient but limited by major drawbacks such as difficult-to-prepare starting materials, use of hazardous solvents, large excess oxidants, and harsh reaction conditions [2,39,40,41]. Thus, the development of more simple and milder methods to synthesize 4(3H)-quinazolinone derivatives remains an attractive task for organic chemists [6,42,43].

Figure 1 Several 4(3H)-quinazolinone derivatives with pharmacological activities.
Figure 1

Several 4(3H)-quinazolinone derivatives with pharmacological activities.

Recently, 4(3H)-quinazolinones could be prepared by a catalytic redox reaction of 2-aminobenzamide and an alcohol alternative to 2-aminobenzoic acid and aldehyde, which are generally unstable and expensive. Transition metals such as palladium, iron, copper, and nickel have been reported to be active sites for this annulation, affording step- and atom-economical protocols [44,45,46,47,48,49] (Figure 2a). For instance, the Pd(ii) complex-catalyzed one-pot synthesis of 4(3H)-quinazolinone from 2-aminobenzamide and a primary alcohol in the presence of m-xylene as the solvent has been reported by Balaji and co-workers [2]. In addition, 4(3H)-quinazolinones could be obtained from aromatic primary alcohols using Ni(ii) or Cu(ii) catalysts in xylene or toluene [50,51]. Obviously, these protocols allowed 4(3H)-quinazolinones to be efficiently produced from more stable and available substrates. However, using such transition metal-based catalysts and organic solvents can lead to environmental concerns about waste disposal and metal contamination in the products [52,53]. Herein, the synthesis of 4(3H)-quinazolinones from 2-aminobenzamides and alcohols under an O2 atmosphere as a green oxidant was investigated (Figure 2b). It was observed that the reaction could readily proceed in the presence of t-BuONa without any additional solvent and transition-metal catalyst, indicating the high potential of this pathway.

Figure 2 Synthesis of 2-phenylquinazolin-4(3H)-ones under solvent-free and transition-metal catalyst-free conditions. (a) Previous works; (b) this work.
Figure 2

Synthesis of 2-phenylquinazolin-4(3H)-ones under solvent-free and transition-metal catalyst-free conditions. (a) Previous works; (b) this work.

2 Materials and methods

2.1 Materials and instrumentation

All chemicals were purchased from Energy Chemical, Xilong, Acros, and GHTech and were used as received without further purification unless otherwise noted. Silica gel 60 F254 plates (20 cm × 20 cm) with a layer thickness of 0.25 mm for thin-layer chromatography (TLC) were purchased from Merck.

Gas chromatography (GC) was performed on a Shimadzu GC 2010-Plus equipped with a flame ionization detector and an SPB-5 column (length = 30 m, inner diameter = 0.25 mm, and film thickness = 0.25 μm). For GC analysis, the sample was initially held at 100°C for 1 min, then heated from 100°C to 280°C with a ramp rate of 40°C·min−1, and further held at 280°C for another 4.5 min before being cooled down to 100°C. The inlet and detector temperatures were maintained at 280°C during the analysis course.

Gas chromatography–mass spectrometry (GC–MS) was conducted on a Shimadzu GC-MS-QP2010 Ultra equipped with a ZB-5MS column (length = 30 m, inner diameter = 0.25 mm, and film thickness = 0.25 μm). For GC–MS analysis, the sample was kept at 50°C for 2 min, then heated from 50°C to 280°C with a ramp rate of 10°C·min−1, and finally kept at 280°C for 10 min. The inlet temperature was maintained at 280°C. The obtained mass spectra were compared with references from the NIST library.

Nuclear magnetic resonance (1H NMR and 13C NMR) spectra were recorded in DMSO-d 6 using the residual solvent peak or tetramethylsilane as a reference on a Bruker AV 500 spectrometer.

The melting points of the isolated products were determined using a Stuart SMP30 device.

2.2 Procedure for the synthesis of 2-phenylquinazolin-4(3H)-one

In a typical experiment, 2-aminobenzamide (40.8 mg, 0.3 mmol), benzyl alcohol (1 mL), and sodium tert-butoxide (43.2 mg, 1.5 equivalents) were sequentially added to an 8-mL vial. The reaction mixture was purged with oxygen 2 min before being tightly sealed. Subsequently, the reaction was performed under vigorous stirring at 120°C. After a predetermined time period, the vial was cooled down to room temperature, and diphenyl ether (51.1 mg, 0.3 mmol) as an internal standard was added. Ethyl acetate (3 mL) was then added to dilute the reaction mixture. An aliquot withdrawn from the resulting mixture was quenched with brine (2 mL), extracted with ethyl acetate (2 mL), dried over anhydrous sodium sulfate, and filtered through a cotton layer. The final organic sample was analyzed by GC using the diphenyl ether internal standard to determine the product yield. To determine the completion of this transformation, the reaction experiments were performed for different time intervals from 0.5 to 30 h.

For the isolation and purification of 2-phenylquinazolin-4(3H)-one, after the reaction described above, the resulting mixture was cooled to room temperature, then diluted with ethyl acetate (20 mL), and quenched with brine (10 mL). The obtained organic phase was dried over anhydrous Na2SO4, filtered through a thin cotton layer, and evaporated under reduced pressure, yielding a solid product. The raw product was further purified by washing with n-hexane (3 × 15 mL), affording 2-phenylquinazolin-4(3H)-one as a white solid. During the isolation and purification steps, TLC was performed using a mixture of ethyl acetate and n-hexane (volume ratio = 1:3). Visualization of the TLC plates was performed under ultraviolet light (254 and 365 nm). The product structure was identified by GC–MS, 1H NMR, and 13C NMR.

3 Results and discussion

According to the previous studies on the synthesis of 2-phenylquinazolin-4(3H)-one via oxidative condensation of 2-aminobenzamide with benzyl alcohol (Figure 3), it was found that the base should be applied to promote the formation of the desired product under the transition-metal-based catalysis [2,48,54]. Initial studies therefore focused on the effect of bases on metal-free transformation. As shown in Table 1, the weak bases including DABCO and Na2CO3 were found to be unsuitable for this reaction, giving only trace amounts of the desired product (Entries 1 and 2). This result is consistent with the previous work of Qiu et al., in which it was suggested that carbonate salts were not strong enough to promote the last dehydrogenation toward 2-phenylquinazolin-4(3H)-one [55]. As can be expected, using stronger bases such as alkali hydroxides and alkali t-butoxide resulted in significantly improved production of quinazolinone. It should be noted that no transition-metal catalysts were present in this protocol. Indeed, a quinazoline yield of 34% could be obtained in the reaction mediated by t-BuOLi, while NaOH, t-BuOK, and KOH, respectively, gave higher yields of the desired product (>60%) (Entries 3–6). Among the tested bases, t-BuONa exhibited the best performance, producing 2-phenylquinazolin-4(3H)-ones with the highest yield of 82%.

Figure 3 Model reaction of 2-aminobenzamide and benzyl alcohol toward 2-phenylquinazolin-4(3H)-one for screening of the reaction conditions.
Figure 3

Model reaction of 2-aminobenzamide and benzyl alcohol toward 2-phenylquinazolin-4(3H)-one for screening of the reaction conditions.

Table 1

Screening of the reaction conditionsa

Entry Temperature (°C) Time (h) Base Base amount (equivalents) Oxidant GC yield (%)
1 140 24 DABCO 1.5 O2 Trace
2 140 24 Na2CO3 1.5 O2 Trace
3 140 24 t-BuOLi 1.5 O2 34
4 140 24 NaOH 1.5 O2 60
5 140 24 t-BuOK 1.5 O2 62
6 140 24 KOH 1.5 O2 63
7 140 24 t-BuONa 1.5 O2 82
8 140 24 t-BuONa 0 O2 Trace
9 140 24 t-BuONa 0.25 O2 9
10 140 24 t-BuONa 0.5 O2 48
11 140 24 t-BuONa 1 O2 65
12 140 24 t-BuONa 2 O2 83
13 RT 24 t-BuONa 1.5 O2 Trace
14 60 24 t-BuONa 1.5 O2 45
15 80 24 t-BuONa 1.5 O2 57
16 100 24 t-BuONa 1.5 O2 68
17 120 24 t-BuONa 1.5 O2 84
18 120 24 t-BuONa 1.5 None (Ar) Trace
19 120 24 t-BuONa 1.5 Air 21
20 120 24 t-BuONa 1.5 DTBP 10
21 120 24 t-BuONa 1.5 H2O2 29b, 46c, 39d
22 120 0.5 t-BuONa 1.5 O2 16
23 120 2.5 t-BuONa 1.5 O2 54
24 120 5 t-BuONa 1.5 O2 58
25 120 15 t-BuONa 1.5 O2 68
26 120 20 t-BuONa 1.5 O2 75
27 120 30 t-BuONa 1.5 O2 84

aGeneral conditions: 2-aminobenzamide (0.3 mmol), benzyl alcohol (1 mL), and a base. bH2O2 (1 equivalent), cH2O2 (2 equivalents), dH2O2 (3 equivalents). DABCO: 1,4-diazabicyclo[2.2.2]octane; t-BuOLi: lithium tert-butoxide; t-BuOK: potassium tert-butoxide; t-BuONa: sodium tert-butoxide.

Furthermore, the impact of the t-BuONa amount on quinazoline production was explored (Entries 7–12). No major product was detected after 24 h in the absence of t-BuONa, verifying the importance of the base for this transformation. The desired product was obtained in a low yield of 9% as 0.25 equivalents of t-BuONa was used. Using more base amounts led to considerable increases in the formation of 2-phenylquinazolin-4(3H)-one. However, using 2 equivalents of t-BuONa was found to be unnecessary, with no further yield improvement obtained.

Next, the reaction of 2-aminobenzamide with benzyl alcohol was investigated at different temperatures ranging from room temperature to 140°C. It was observed that the reaction temperature greatly impacted on the production of 2-phenylquinazolin-4(3H)-one (Entries 13–17). No reaction toward quinazolinone was observed at room temperature. As expected, conducting the reactions at elevated temperatures, namely, 60°C, 80°C, 100°C, and 120°C, gave higher product yields of 45%, 57%, 68%, and 84%, respectively. No further enhancement in the formation of the desired product was observed when the reaction temperature was increased to 140°C. In general, under transition-metal-free conditions, a higher temperature was required to obtain 2-phenylquinazolin-4(3H)-one compared to the previous studies, in which the metal catalysts allowed the reaction to take place under milder conditions. Indeed, using α -MnO2 as the solid catalyst for this reaction was reported by Zhang and co-workers, giving the desired product in a good yield of 79% at 80°C [45]. Furthermore, the coupling of 2-aminobenzamide with alcohol catalyzed by iron(iii) nitrate readily produced 2-phenylquinazolin-4(3H)-one at 100°C [48].

In this study, benzyl alcohol could play a dual role in the reactant and the reaction medium. Therefore, the amount of benzyl alcohol was also an important factor that should be concerned to afford the desired product in high yields (Entries 1–6, Table S1 in Supplementary material). It was observed that the reaction using 0.25 mL of benzyl alcohol produced 2-phenylquinazolin-4(3H)-one in a moderate yield of 57%, probably due to the hindered interaction of solid substrates, namely, 2-aminobenzamide and t-BuONa, with benzyl alcohol in a limited amount (Entry 1). Therefore, adding more 0.5 and 0.75 mL of benzyl alcohol significantly accelerated the transformation, increasing the yield of 2-phenylquinazolin-4(3H)-one to 70% and 76%, respectively (Entries 2–3). As expected, the reaction proceeded more readily in the presence of 1 mL of benzyl alcohol, affording a yield of 84% (Entry 4). However, no notable differences in the reaction performance were observed in the benzyl alcohol amount range of 1.0–1.5 mL with product yields of around 80% recorded (Entries 4–6).

As previously reported, an oxidant was required to convert benzyl alcohol to benzaldehyde, which was proposed as an important intermediate in the formation of 2-phenylquinazolin-4(3H)-ones [7,55]. In this study, various oxidative conditions were therefore tested for the reaction. The results in Table 1 (Entries 17–21) indicated that the transformation toward 2-phenylquinazolin-4(3H)-one strongly depended on the oxidant nature. As predicted, no desired product was obtained under an argon atmosphere, while the reaction could proceed slowly in air, finally giving a poor yield of 21% after 24 h, probably due to a shortage of oxygen for the oxidation of benzyl alcohol. Indeed, 2-phenylquinazolin-4(3H)-one was favorably generated under an O2 atmosphere in 84% yield. Furthermore, other liquid oxidants, including DTBP and H2O2, with different amounts exhibited poor performances with low yields of 2-phenylquinazolin-4(3H)-ones (10–50%). These results could be rationalized by the fact that using such strong oxidants could lead to unwanted oxidation of the amine group in 2-aminobenzamide at an elevated temperature. O2 emerges as a green, cheap, and efficient oxidant for this annulation.

To emphasize the efficiency of the pathway under solvent-free conditions, various polar and non-polar solvents were added to the reaction, and the yield results are presented in Table S1. The presence of water, a protic solvent, completely shut down the reaction, while low yields of 2-phenylquinazolin-4(3H)-one (15–39%) were obtained in the reactions containing polar aprotic solvents, namely, DMF and DMSO (Entries 7–9). The earlier studies indeed reported that such polar solvents were incompatible with converting benzyl alcohol and 2-aminobenzamide into 2-phenylquinazolin-4(3H)-one [55,56]. Interestingly, better performances were obtained when less polar and non-polar solvents, including 1,2-dichlorobenzene and toluene, respectively, were added (Entries 10 and 11). In a similar work on the oxidative synthesis of 2-phenylquinazolin-4(3H)-one from benzyl alcohol and 2-aminobenzamide, a large amount of toluene solvent was also required [55]. However, organic solvents usually cause serious problems related to human health, eco-system, and safety due to their high toxicity and flammability. In addition, the work-up procedure would be more complicated for the removal and disposal of the organic solvents. Solvent-free conditions are therefore highly desired. Notably, it was found that the solvent-free reaction produced 2-phenylquinazolin-4(3H)-one with the best yield of 84%, highlighting the undeniable benefits of this annulation.

Finally, the reaction of 2-aminobenzamide and benzyl alcohol was carried out in the time range from 0.5 to 30 h (Entries 22–27, Table 1). The kinetic investigation of the reaction revealed that conversion to 2-phenylquinazolin-4(3H)-one promptly proceeded in the first 2.5 h, affording a 54% yield. Prolonging the reaction to 24 h led to an additional yield of approx. 30%; however, this yield value was maintained in the 30-h reaction. Notably, a large-scale reaction involving 2.0 mmol of 2-aminobenzamide and 32 equivalents of benzyl alcohols was also performed under identical conditions investigated. After a simple purification procedure without column chromatography, the major product, 2-phenylquinazolin-4(3H)-one, could be successfully obtained in a well-isolated yield of 70%, showing the great potential of this transition-metal catalyst-free pathway.

To investigate the transformation mechanism, a series of control experiments were carried out. As mentioned previously, no 2-phenylquinazolin-4(3H)-one was obtained in the absence of either oxygen or t-BuONa (Figure 4a and b). On the other hand, the treatment of benzyl alcohol under the established conditions without adding 2-aminobenzamide resulted in the observation of benzaldehyde, implying that benzaldehyde could be formed via the oxidation of benzyl alcohol in the presence of t-BuONa and oxygen (Figure 4c). Notably, benzaldehyde and dihydrogenated quinazolinone were also detected as the intermediates when the standard reaction was performed within 5 h (Figure 4d). To investigate the role of t-BuONa in this pathway, the reaction of 2-aminobenzamide and benzaldehyde was carried out under identical conditions in the absence of t-BuONa, giving quinazolinone in an excellent yield (96%) (Figure 4e). It was therefore suggested that t-BuONa could accelerate the oxidation of benzyl alcohol to benzaldehyde, which would participate in the next condensation reaction with 2-aminobenzamide. Note that benzaldehyde and its derivatives are organic compounds highly sensitive to air, light, and moisture. Benzaldehyde spontaneously undergoes unexpected oxidation to yield benzoic acid upon exposure to air under ambient conditions, while the presence of such an impurity can significantly affect the reaction involving benzaldehyde [57]. Therefore, preservation of benzaldehyde under an inert atmosphere or purification of benzaldehyde prior to use is usually required with high consumption of cost and energy. From the viewpoint of green chemistry, benzyl alcohol has emerged as a more stable, more available, and less costly starting material alternative to benzaldehyde in numerous organic transformation reactions [58,59,60,61]. In this study, the use of benzyl alcohols with the assistance of a base indeed offered an environmentally benign and efficient pathway for synthesizing 2-phenylquinazolin-4(3H)-ones.

Figure 4 Control experiments.
Figure 4

Control experiments.

Interestingly, in the reaction of 2-aminobenzamide with benzaldehyde under t-BuONa- and O2-free conditions, only a 12% yield for the major product was obtained, while a large amount of dihydrogenated quinazolinone was produced (Figure 4f), implying the essential role of O2 in the dehydrogenative step of dihydrogenated quinazolinone to quinazolinone [2,51]. Based on the obtained results, the pathway for t-BuONa-promoted oxidative coupling of 2-aminobenzamide with benzyl alcohol toward 2-phenylquinazolin-4(3H)-one was proposed (Figure 5). With the assistance of t-BuONa, benzyl alcohol was first oxidized by O2 at a high temperature to benzaldehyde, which underwent condensation with 2-aminobenzamide to produce imine a. Subsequently, an intramolecular nucleophilic addition allowed the conversion of a into dihydrogenated quinazolinone b, which was dehydrogenated by oxygen to finally yield the desired product.

Figure 5 Plausible mechanism for forming 2-phenylquinazolin-4(3H)-one from 2-aminobenzamide and benzyl alcohol in the presence of O2 and t-BuONa.
Figure 5

Plausible mechanism for forming 2-phenylquinazolin-4(3H)-one from 2-aminobenzamide and benzyl alcohol in the presence of O2 and t-BuONa.

With the optimal conditions in hand, the substrate scope was expanded to the synthesis of 2-phenylquinazolin-4(3H)-one derivatives from substituted 2-aminobenzamides and benzyl alcohols (Table 2). The standard reaction of 2-aminobenzamide with benzyl alcohol produced 2-phenylquinazolin-4(3H)-one in an isolated yield of 75% (Entry 1). Good yields of quinazolin-4(3H)-ones also remained in the reactions using benzyl alcohols containing an electron-donating group, in good agreement with the study on the Ni-catalyzed synthesis of quinazolin-4(3H)-one derivatives from 2-aminobenzamide and benzyl alcohols [51]. Indeed, 3-methylbenzyl alcohol and 4-methylbenzyl alcohol (Entries 2 and 3) afforded the corresponding quinazolin-4(3H)-ones in 67% and 69% isolated yields, respectively. A similar result was also obtained for the case of 4-methoxybenzyl alcohol (66%, Entry 4). By contrast, electron-withdrawing groups in benzyl alcohol significantly inhibited the production of 2-phenylquinazolin-4(3H)-one. The reaction of 2-aminobenzamide with 2-chlorobenzyl alcohol or 3-chlorobenzyl alcohol gave low quinazolinone yields of 31% and 29%, respectively (Entries 5 and 6). These results indicated negligible steric hindrance of the substituent at the ortho position of benzyl alcohol. Besides, no desired products were observed in the reaction involving 2-nitro or 4-nitrobenzyl alcohols (Entries 7 and 8). Next, several substituted 2-aminobenzamides were also used to react with benzyl alcohol under identical conditions. This annulation showed good tolerance to both the electron-donating (methyl-) and electron-withdrawing (fluoro-, chloro-) groups in 2-aminobenzamide, affording the corresponding products in good yields of 51–63% (Entries 9–11).

Table 2

Oxidative coupling between o-aminobenzamides and benzyl alcohols to 2-phenylquinazolin-4(3H)-ones in the presence of t-BuONa and O2 a

Entry Reactant 1 Reactant 2 Product Isolated yield (%) Melting point (°C)
1 75 230–232
2 67 208–210
3 69 230–232
4 66 242–244
5 31 198–200
6 29 298–300
7 Trace —
8 Trace —
9 57 236–238
10 51 291 (decomposed)
11 63 254 (decomposed)

aReaction conditions: reactant 1 (0.3 mmol), reactant 2 (32 equivalents), t-BuONa (1.5 equivalents), 120°C, under an O2 atmosphere for 24 h.

4 Conclusions

In this study, 2-phenylquinazolin-4(3H)-one was successfully synthesized from more stable and available substrates, namely, 2-aminobenzamide and benzyl alcohol, in the presence of a strong base and oxygen as a green and cheap oxidant without further use of any additional solvent and transition-metal catalyst. The mechanistic experiments provided reliable evidence for the in situ formation of benzaldehyde via t-BuONa-assisted oxidation of benzyl alcohol followed by coupling with 2-aminobenzamide and oxidative dehydrogenation to the desired products. The oxidative annulation demonstrated remarkable tolerance with different functional groups in 2-aminobenzamide and benzyl alcohol. The corresponding quinazolin-4(3H)-one derivatives could be obtained in the isolated yields of 29–75%. The significant results of this study are expected to guide a simple, efficient, and environmentally friendly approach to form the quinazolin-4(3H)-one moiety in biologically active molecules.

Acknowledgements

The authors acknowledge Ho Chi Minh City University of Technology (HCMUT), VNU-HCM for supporting this study. The authors would like to thank Van T. T. Nguyen for supporting the experiments.

  1. Funding information: The authors state no funding is involved.

  2. Author contributions: Ha V. Le, Khoa D. Nguyen, Tung T. Nguyen: conceptualization; Vy T. B. Nguyen, Dat P. Tran: formal analysis; Vy T. B. Nguyen, Dat P. Tran: investigation; Tung T. Nguyen: methodology; Ha V. Le, Khoa D. Nguyen: supervision; Tung T. Nguyen: validation; Vy T. B. Nguyen, Ha V. Le: writing – original draft; all authors: writing – review and editing. All authors have read and agreed to the submitted version of the manuscript.

  3. Conflict of interest: The authors state no conflict of interest.

  4. Data availability statement: The datasets generated during and/or analysed during the current study are available from the corresponding author on reasonable request.

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Received: 2022-12-14
Revised: 2023-04-03
Accepted: 2023-04-24
Published Online: 2023-05-23

© 2023 the author(s), published by De Gruyter

This work is licensed under the Creative Commons Attribution 4.0 International License.

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https://doi.org/10.1515/gps-2022-8148
Keywords for this article
2-phenylquinazolin-4(3H)-one; benzyl alcohol; green conditions; oxidative coupling
Creative Commons
BY 4.0

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  18. Synthesis, characterization, anticancer, anti-inflammatory activities, and docking studies of 3,5-disubstituted thiadiazine-2-thiones
  19. Synthesis and stability of phospholipid-encapsulated nano-selenium
  20. Putative anti-proliferative effect of Indian mustard (Brassica juncea) seed and its nano-formulation
  21. Enrichment of low-grade phosphorites by the selective leaching method
  22. Electrochemical analysis of the dissolution of gold in a copper–ethylenediamine–thiosulfate system
  23. Characterisation of carbonate lake sediments as a potential filler for polymer composites
  24. Evaluation of nano-selenium biofortification characteristics of alfalfa (Medicago sativa L.)
  25. Quality of oil extracted by cold press from Nigella sativa seeds incorporated with rosemary extracts and pretreated by microwaves
  26. Heteropolyacid-loaded MOF-derived mesoporous zirconia catalyst for chemical degradation of rhodamine B
  27. Recovery of critical metals from carbonatite-type mineral wastes: Geochemical modeling investigation of (bio)hydrometallurgical leaching of REEs
  28. Photocatalytic properties of ZnFe-mixed oxides synthesized via a simple route for water remediation
  29. Attenuation of di(2-ethylhexyl)phthalate-induced hepatic and renal toxicity by naringin nanoparticles in a rat model
  30. Novel in situ synthesis of quaternary core–shell metallic sulfide nanocomposites for degradation of organic dyes and hydrogen production
  31. Microfluidic steam-based synthesis of luminescent carbon quantum dots as sensing probes for nitrite detection
  32. Transformation of eggshell waste to egg white protein solution, calcium chloride dihydrate, and eggshell membrane powder
  33. Preparation of Zr-MOFs for the adsorption of doxycycline hydrochloride from wastewater
  34. Green nanoarchitectonics of the silver nanocrystal potential for treating malaria and their cytotoxic effects on the kidney Vero cell line
  35. Carbon emissions analysis of producing modified asphalt with natural asphalt
  36. An efficient and green synthesis of 2-phenylquinazolin-4(3H)-ones via t-BuONa-mediated oxidative condensation of 2-aminobenzamides and benzyl alcohols under solvent- and transition metal-free conditions
  37. Chitosan nanoparticles loaded with mesosulfuron methyl and mesosulfuron methyl + florasulam + MCPA isooctyl to manage weeds of wheat (Triticum aestivum L.)
  38. Synergism between lignite and high-sulfur petroleum coke in CO2 gasification
  39. Facile aqueous synthesis of ZnCuInS/ZnS–ZnS QDs with enhanced photoluminescence lifetime for selective detection of Cu(ii) ions
  40. Rapid synthesis of copper nanoparticles using Nepeta cataria leaves: An eco-friendly management of disease-causing vectors and bacterial pathogens
  41. Study on the photoelectrocatalytic activity of reduced TiO2 nanotube films for removal of methyl orange
  42. Development of a fuzzy logic model for the prediction of spark-ignition engine performance and emission for gasoline–ethanol blends
  43. Micro-impact-induced mechano-chemical synthesis of organic precursors from FeC/FeN and carbonates/nitrates in water and its extension to nucleobases
  44. Green synthesis of strontium-doped tin dioxide (SrSnO2) nanoparticles using the Mahonia bealei leaf extract and evaluation of their anticancer and antimicrobial activities
  45. A study on the larvicidal and adulticidal potential of Cladostepus spongiosus macroalgae and green-fabricated silver nanoparticles against mosquito vectors
  46. Catalysts based on nickel salt heteropolytungstates for selective oxidation of diphenyl sulfide
  47. Powerful antibacterial nanocomposites from Corallina officinalis-mediated nanometals and chitosan nanoparticles against fish-borne pathogens
  48. Removal behavior of Zn and alkalis from blast furnace dust in pre-reduction sinter process
  49. Environmentally friendly synthesis and computational studies of novel class of acridinedione integrated spirothiopyrrolizidines/indolizidines
  50. The mechanisms of inhibition and lubrication of clean fracturing flowback fluids in water-based drilling fluids
  51. Adsorption/desorption performance of cellulose membrane for Pb(ii)
  52. A one-pot, multicomponent tandem synthesis of fused polycyclic pyrrolo[3,2-c]quinolinone/pyrrolizino[2,3-c]quinolinone hybrid heterocycles via environmentally benign solid state melt reaction
  53. Green synthesis of silver nanoparticles using durian rind extract and optical characteristics of surface plasmon resonance-based optical sensor for the detection of hydrogen peroxide
  54. Electrochemical analysis of copper-EDTA-ammonia-gold thiosulfate dissolution system
  55. Characterization of bio-oil production by microwave pyrolysis from cashew nut shells and Cassia fistula pods
  56. Green synthesis methods and characterization of bacterial cellulose/silver nanoparticle composites
  57. Photocatalytic research performance of zinc oxide/graphite phase carbon nitride catalyst and its application in environment
  58. Effect of phytogenic iron nanoparticles on the bio-fortification of wheat varieties
  59. In vitro anti-cancer and antimicrobial effects of manganese oxide nanoparticles synthesized using the Glycyrrhiza uralensis leaf extract on breast cancer cell lines
  60. Preparation of Pd/Ce(F)-MCM-48 catalysts and their catalytic performance of n-heptane isomerization
  61. Green “one-pot” fluorescent bis-indolizine synthesis with whole-cell plant biocatalysis
  62. Silica-titania mesoporous silicas of MCM-41 type as effective catalysts and photocatalysts for selective oxidation of diphenyl sulfide by H2O2
  63. Biosynthesis of zinc oxide nanoparticles from molted feathers of Pavo cristatus and their antibiofilm and anticancer activities
  64. Clean preparation of rutile from Ti-containing mixed molten slag by CO2 oxidation
  65. Synthesis and characterization of Pluronic F-127-coated titanium dioxide nanoparticles synthesized from extracts of Atractylodes macrocephala leaf for antioxidant, antimicrobial, and anticancer properties
  66. Effect of pretreatment with alkali on the anaerobic digestion characteristics of kitchen waste and analysis of microbial diversity
  67. Ameliorated antimicrobial, antioxidant, and anticancer properties by Plectranthus vettiveroides root extract-mediated green synthesis of chitosan nanoparticles
  68. Microwave-accelerated pretreatment technique in green extraction of oil and bioactive compounds from camelina seeds: Effectiveness and characterization
  69. Studies on the extraction performance of phorate by aptamer-functionalized magnetic nanoparticles in plasma samples
  70. Investigation of structural properties and antibacterial activity of AgO nanoparticle extract from Solanum nigrum/Mentha leaf extracts by green synthesis method
  71. Green fabrication of chitosan from marine crustaceans and mushroom waste: Toward sustainable resource utilization
  72. Synthesis, characterization, and evaluation of nanoparticles of clodinofop propargyl and fenoxaprop-P-ethyl on weed control, growth, and yield of wheat (Triticum aestivum L.)
  73. The enhanced adsorption properties of phosphorus from aqueous solutions using lanthanum modified synthetic zeolites
  74. Separation of graphene oxides of different sizes by multi-layer dialysis and anti-friction and lubrication performance
  75. Visible-light-assisted base-catalyzed, one-pot synthesis of highly functionalized cinnolines
  76. The experimental study on the air oxidation of 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid with Co–Mn–Br system
  77. Highly efficient removal of tetracycline and methyl violet 2B from aqueous solution using the bimetallic FeZn-ZIFs catalyst
  78. A thermo-tolerant cellulase enzyme produced by Bacillus amyloliquefaciens M7, an insight into synthesis, optimization, characterization, and bio-polishing activity
  79. Exploration of ketone derivatives of succinimide for their antidiabetic potential: In vitro and in vivo approaches
  80. Ultrasound-assisted green synthesis and in silico study of 6-(4-(butylamino)-6-(diethylamino)-1,3,5-triazin-2-yl)oxypyridazine derivatives
  81. A study of the anticancer potential of Pluronic F-127 encapsulated Fe2O3 nanoparticles derived from Berberis vulgaris extract
  82. Biogenic synthesis of silver nanoparticles using Consolida orientalis flowers: Identification, catalytic degradation, and biological effect
  83. Initial assessment of the presence of plastic waste in some coastal mangrove forests in Vietnam
  84. Adsorption synergy electrocatalytic degradation of phenol by active oxygen-containing species generated in Co-coal based cathode and graphite anode
  85. Antibacterial, antifungal, antioxidant, and cytotoxicity activities of the aqueous extract of Syzygium aromaticum-mediated synthesized novel silver nanoparticles
  86. Synthesis of a silica matrix with ZnO nanoparticles for the fabrication of a recyclable photodegradation system to eliminate methylene blue dye
  87. Natural polymer fillers instead of dye and pigments: Pumice and scoria in PDMS fluid and elastomer composites
  88. Study on the preparation of glycerylphosphorylcholine by transesterification under supported sodium methoxide
  89. Wireless network handheld terminal-based green ecological sustainable design evaluation system: Improved data communication and reduced packet loss rate
  90. The optimization of hydrogel strength from cassava starch using oxidized sucrose as a crosslinking agent
  91. Green synthesis of silver nanoparticles using Saccharum officinarum leaf extract for antiviral paint
  92. Study on the reliability of nano-silver-coated tin solder joints for flip chips
  93. Environmentally sustainable analytical quality by design aided RP-HPLC method for the estimation of brilliant blue in commercial food samples employing a green-ultrasound-assisted extraction technique
  94. Anticancer and antimicrobial potential of zinc/sodium alginate/polyethylene glycol/d-pinitol nanocomposites against osteosarcoma MG-63 cells
  95. Nanoporous carbon@CoFe2O4 nanocomposite as a green absorbent for the adsorptive removal of Hg(ii) from aqueous solutions
  96. Characterization of silver sulfide nanoparticles from actinobacterial strain (M10A62) and its toxicity against lepidopteran and dipterans insect species
  97. Phyto-fabrication and characterization of silver nanoparticles using Withania somnifera: Investigating antioxidant potential
  98. Effect of e-waste nanofillers on the mechanical, thermal, and wear properties of epoxy-blend sisal woven fiber-reinforced composites
  99. Magnesium nanohydroxide (2D brucite) as a host matrix for thymol and carvacrol: Synthesis, characterization, and inhibition of foodborne pathogens
  100. Synergistic inhibitive effect of a hybrid zinc oxide-benzalkonium chloride composite on the corrosion of carbon steel in a sulfuric acidic solution
  101. Review Articles
  102. Role and the importance of green approach in biosynthesis of nanopropolis and effectiveness of propolis in the treatment of COVID-19 pandemic
  103. Gum tragacanth-mediated synthesis of metal nanoparticles, characterization, and their applications as a bactericide, catalyst, antioxidant, and peroxidase mimic
  104. Green-processed nano-biocomposite (ZnO–TiO2): Potential candidates for biomedical applications
  105. Reaction mechanisms in microwave-assisted lignin depolymerisation in hydrogen-donating solvents
  106. Recent progress on non-noble metal catalysts for the deoxydehydration of biomass-derived oxygenates
  107. Rapid Communication
  108. Phosphorus removal by iron–carbon microelectrolysis: A new way to achieve phosphorus recovery
  109. Special Issue: Biomolecules-derived synthesis of nanomaterials for environmental and biological applications (Guest Editors: Arpita Roy and Fernanda Maria Policarpo Tonelli)
  110. Biomolecules-derived synthesis of nanomaterials for environmental and biological applications
  111. Nano-encapsulated tanshinone IIA in PLGA-PEG-COOH inhibits apoptosis and inflammation in cerebral ischemia/reperfusion injury
  112. Green fabrication of silver nanoparticles using Melia azedarach ripened fruit extract, their characterization, and biological properties
  113. Green-synthesized nanoparticles and their therapeutic applications: A review
  114. Antioxidant, antibacterial, and cytotoxicity potential of synthesized silver nanoparticles from the Cassia alata leaf aqueous extract
  115. Green synthesis of silver nanoparticles using Callisia fragrans leaf extract and its anticancer activity against MCF-7, HepG2, KB, LU-1, and MKN-7 cell lines
  116. Algae-based green AgNPs, AuNPs, and FeNPs as potential nanoremediators
  117. Green synthesis of Kickxia elatine-induced silver nanoparticles and their role as anti-acetylcholinesterase in the treatment of Alzheimer’s disease
  118. Phytocrystallization of silver nanoparticles using Cassia alata flower extract for effective control of fungal skin pathogens
  119. Antibacterial wound dressing with hydrogel from chitosan and polyvinyl alcohol from the red cabbage extract loaded with silver nanoparticles
  120. Leveraging of mycogenic copper oxide nanostructures for disease management of Alternaria blight of Brassica juncea
  121. Nanoscale molecular reactions in microbiological medicines in modern medical applications
  122. Synthesis and characterization of ZnO/β-cyclodextrin/nicotinic acid nanocomposite and its biological and environmental application
  123. Green synthesis of silver nanoparticles via Taxus wallichiana Zucc. plant-derived Taxol: Novel utilization as anticancer, antioxidation, anti-inflammation, and antiurolithic potential
  124. Recyclability and catalytic characteristics of copper oxide nanoparticles derived from bougainvillea plant flower extract for biomedical application
  125. Phytofabrication, characterization, and evaluation of novel bioinspired selenium–iron (Se–Fe) nanocomposites using Allium sativum extract for bio-potential applications
  126. Erratum
  127. Erratum to “Synthesis, characterization, and evaluation of nanoparticles of clodinofop propargyl and fenoxaprop-P-ethyl on weed control, growth, and yield of wheat (Triticum aestivum L.)”
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