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A convenient synthesis of coumarinyl chalcones using HClO4–SiO2: A green approach
⁎Tel.: +91 9412653054. siddiqui_zeba@yahoo.co.in (Zeba N. Siddiqui)
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Received: ,
Accepted: ,
This article was originally published by Elsevier and was migrated to Scientific Scholar after the change of Publisher.
Peer review under responsibility of King Saud University.
Abstract
A simple and efficient one-pot synthesis of coumarinyl chalcones was reported in the presence of silica supported perchloric acid under solvent-free heating at 80 °C in excellent yields. The catalyst was recycled for four runs without any loss of its catalytic activity.
Abstract
HClO4–SiO2 catalyzed synthesis of coumarinyl chalcones (8a–j) under solvent-free conditions is reported. The catalyst is characterized by powder XRD and SEM–EDX analysis. The stability of the catalyst is evaluated by thermogravimetric (TG) and differential scanning calorimetry (DSC) techniques. The remarkable features of this green protocol are the excellent yields of the products, shorter reaction time, simple experimental procedure, easy preparation and reusability of the catalyst.
Keywords
HClO4–SiO2
Coumarinyl chalcones
Heterogeneous catalyst
Thermal solvent-free conditions
1 Introduction
Green chemistry approach proposes significant potential in the development of new methodologies in organic synthesis. In this regard, some appropriate ways are to utilize eco-friendly, non-hazardous, reproducible and efficient catalysts/solvents and energy sustainable processes (Anastas and Warner, 1998). The concept of heterogeneous catalysis has become extremely important in green chemistry for the development of greener and safe reaction methodologies (Lancaster, 2002). In this context, recoverable and recyclable catalysts play a key role due to environmental and economical impacts. One of the promising routes to synthesize heterogeneous catalyst is to support the conventional catalyst on porous inorganic solids such as silica, alumina, titania, zirconia, zeolite, etc. (Smith and Horwood, 1992; Kumar et al., 2013). Among different supported catalysts, silica supported catalysts have attracted considerable attention of chemists in recent years due to their large surface area, better selectivity, high mechanical and thermal stability, easy to handle, and long catalytic life which make it promising for both academic and industrial applications (Smith and Horwood, 1992; Li et al., 2007a, 2007b). In this context, HClO4–SiO2 is a suitable candidate for various organic reactions due to its inherent properties such as high acidity, efficiency, stability, inexpensiveness, recyclability, selectivity, operational simplicity, non-corrosiveness, moisture-insensitivity and easy handling etc. (Das et al., 2006; Chakraborti and Gulhane, 2003). It has been successfully employed for numerous organic reactions, such as the protection of hydroxyl groups (Shaterian et al., 2007), acetylation of phenols, thiols, alcohols, amines (Chakraborti and Gulhane, 2003), synthesis of xanthenes (Bigdeli et al., 2007a, 2007b)/substituted coumarins (Maheswara et al., 2006)/chromenyl pyridines (Ghashang et al., 2014)/β-keto enol ethers (Das et al., 2007a, 2007b)/quinoxalines and dihydropyrazines (Das et al., 2007a, 2007b)/flavans (Bharate et al., 2012)/enaminones and enamino esters (Das et al., 2007a, 2007b)/acylals (Kamble et al., 2006) and chemoselective carbon sulfur bond formation (Khatik et al., 2007). It has been also applied in Hantzsch (Dasri et al., 2011), Winkler (Heydari and MaMani, 2008), Mannich (Bigdeli et al., 2007a, 2007b) and Biginelli (Maheswara et al., 2008) reactions.
Coumarin based chalcones are reported for their anticancer (Sashidhara et al., 2010), antioxidant, antibacterial (Hamdi et al., 2010), anti-inflammatory (Sashidhara et al., 2011), antiviral (Trivedi et al., 2007), trypanocidal (Vazquez-Rodriguez et al., 2013), analgesic (Jayashree et al., 2009) and antiproliferative (Patel et al., 2011) activities. Recent research suggests that the fusion of a chalcone moiety with the coumarin ring may be promising for the synthesis of derivatives with enhanced TPA (two-photon absorption) cross-sections (Li et al., 2007a, 2007b). Synthesis of coumarin based chalcones disclosed in the literature is associated with the use of toxic solvents/catalysts/reagents, high reaction temperature, prolonged reaction time, and laborious work-up procedures (Sashidhara et al., 2010, 2011; Hamdi et al., 2010). Therefore, the discovery of new and sustainable protocols for the synthesis of these privileged medicinal scaffolds is of prime importance. It was visualized therefore, to explore the synthesis of coumarinyl chalcones using HClO4–SiO2 due to the above mentioned biological properties associated with this class of heterocyclic compounds.
Thus, based on the above findings and in continuation of our interest for the synthesis of coumarin and chalcone derivatives (Siddiqui and Ahmed, 2013; Siddiqui et al., 2008) we report herein, the use of silica supported perchloric acid (HClO4–SiO2) as highly efficient, and recyclable heterogeneous catalyst for the synthesis of coumarin based chalcones under thermal solvent-free conditions in excellent yields.
2 Experimental
2.1 General
Melting points of all synthesized compounds were taken in a Reichert Thermovar instrument and are uncorrected. The IR spectra (KBr) were recorded on Perkin Elmer RXI spectrometer. 1H NMR and 13C NMR spectra were recorded on a Bruker DRX-300 and Bruker Avance II 400 spectrometer using tetramethylsilane (TMS) as an internal standard and DMSO-d6/CDCl3 as a solvent. Chemical shifts are given in parts per million and coupling constants in Hertz. DART-MS were recorded on a JEOL-Accu TOF JMS-T100LC mass spectrometer having a DART source. Elemental analyses (C, H and N) were conducted using the Elemental vario EL III elemental analyzer and their results were found to be in agreement with the calculated values. 5-Acetyl-1,3-dimethylbarbituric acid, 5-acetyl-barbituric acid, 5-acetyl-thiobarbituric acid, 3-acetyl-4-hydroxycoumarin and 4-chloro-3-formylcoumarin were synthesized by the reported procedures (Jursic and Neumann, 2001; Hamdi et al., 2011). Other chemicals were of commercial grade and used without further purification. The homogeneity of the compounds was checked by thin layer chromatography (TLC) on glass plates coated with silica gel G254 (E. Merck) using chloroform–methanol (3:1) mixture as mobile phase and visualized using iodine vapors. X-ray diffractograms (XRD) of the catalyst were recorded in the 2θ range of 10–70° with a scan rate of 4°/min on a Rigaku Minifax X-ray diffractometer with Ni-filtered Cu Kα radiation at a wavelength of 1.54060 Å. The SEM–EDX characterization of the catalyst was performed on a JEOL JSM-6510 scanning electron microscope equipped with energy dispersive X-ray spectrometer operating at 20 kV. DSC and TGA data were obtained with DSC-60 Shimadzu instrument.
2.2 Synthesis of catalyst (HClO4–SiO2)
The catalyst, silica-supported perchloric acid (HClO4–SiO2), was prepared by the reported procedure (Chakraborti and Gulhane, 2003). To confirm the formation of expected catalytic system, EDX analysis (Fig. 1) was carried out which showed the presence of Cl, O and Si elements.
The thermal stability of the catalyst was evaluated by DSC analysis. The peak at temperature 100 °C represented the removal of adsorbed water molecules from the support framework. The absence of any other peak up to 500 °C denoted the stability of the catalyst up to this temperature (Fig. 2).
Thermogravimetric analysis (Fig. 3) of HClO4–SiO2 indicated the weight loss of 22.0% near to 200 °C due to loss of water molecules trapped in the support framework and did not show any other significant weight loss up to 500 °C which denoted the stability of catalyst.
The DTA curve showed endothermic peak between 100 and 200 °C which can be attributed to the evaporation of residual water molecules from polymer matrix (Fig. 4).
Powder XRD pattern (Fig. 5a) showed amorphous nature of the catalyst. A broad peak situated at 2θ ∼ 22° attributed to silica.
SEM images of HClO4–SiO2 have been shown in (Fig. 6a and b).
2.3 General procedure for the synthesis of coumarinyl chalcones under thermal solvent-free conditions
To a mixture of aldehyde (1–6) (1.00 mmol) and heterocyclic methyl ketones (7a–e) (1.00 mmol), HClO4–SiO2 (100 mg) was added. The reaction mixture was heated at 80 °C for specified time (Table 7). After completion of the reaction (checked by TLC), the reaction mixture was cooled to room temperature and mixed thoroughly with ethyl acetate (10 mL). The solid inorganic material was filtered off. After separation of solid, the solvent was evaporated under the reduced pressure. The orange/yellow solid, thus, obtained was washed with water and dried. Further purification was made by recrystallization from ethanol to afford pure products 8a–j.
2.4 Spectroscopic data of novel compounds (8a-e)
2.4.1 (2E)-1-(4-hydroxy-1-benzopyran-2-one-3-yl)-3-(4-chloro-1-benzopyran-2-one-3-yl)-2-propen-1-one (8a)
Orange solid, mp 220–225 °C. IR (KBr) (υmax, cm−1): 3130 (OH), 1722 (C⚌O), 1650 (C⚌O), 1599 (C⚌C). 1H NMR (DMSO, 400 MHz,) δ 8.92 (1H, d, J = 15.7, Ha), 8.17 (1H, d, J = 15.7, Hb), 7.94–7.36 (8H, m, Ar—H), 13C NMR (DMSO, 100 MHz) δ 182.0 (C-3′), 178.6 (C-4″), 162.0, 161.2(C-2, C-2″), 154.7 (C-1′), 152.3, 151.9 (C-9, C-9″), 136.7 (C-4), 132.6 (C-10), 124.5 (C-2′), 123.5 (C-3), 122.6 (C-3), 131.8, 117.9, 117.1, 115.8, 112.9 (C—Ar), 102.2 (C-3″). ESI-MS (m/z) 394.6 (M+). Anal. Calcd. (C21H11ClO6): C, 64.01; H, 2.81, Anal. Found (C21H11ClO6): C, 64.32; H, 3.16.
2.4.2 (2E)-1-(4-hydroxy-6-methyl-2-oxo-2-H-pyran-3-yl)-3-(4-chloro-1-benzopyran-2-one-3-yl)-2-propen-1-one (8b)
Orange solid, mp 232–237 °C. IR (KBr) (υmax, cm−1): 3074 (OH), 1727 (C⚌O), 1644 (C⚌O), 1600 (C⚌C). 1H NMR (DMSO, 400 MHz,) δ 8.72 (1H, d, J = 15.7, Ha), 8.02 (1H, d, J = 15.7, Hb), 7.87–7.36 (4H, m, Ar-H), 6.13 (1H, s, H-5), 2.18 (s, 3H, CH3). 13C NMR (DMSO, 100 MHz,) δ 182.3 (C-3′), 165.9 (C-6″), 162.0 (C-2), 161.2 (C-2″), 154.7 (C-1′), 152.3 (C-9), 136.9 (C-4), 132.6 (C-10), 131.8, 124.5 (C-2′), 123.6, 122.6, 119.4 (C—Ar), 102.2 (C-3″), 99.5 (C-5″), 25.2 (CH3). ESI-MS (m/z) 358.8 (M+). Anal. Calcd. (C18H11ClO6): C, 60.30; H, 3.09, Anal. Found (C18H11ClO6): C, 60.59; H, 2.76.
2.4.3 (2E)-1-(1,3-dimethyl-2,4,6-pyrimidinetrione-5-yl)-3-(4-chloro-1-benzopyran-2-one-3-yl)-2-propen-1-one (8c)
Orange solid, mp >300 °C. IR (KBr) (υmax, cm−1): 1712 (C⚌O), 1656 (C⚌O), 1596 (C⚌C). 1H NMR (DMSO, 400 MHz,) δ 9.06 (1H, d, J = 15.8, Ha), 8.73 (1H, d, J = 15.5, Hb), 8.09–7.33 (4H, m, Ar—H), 3.63 (s, 3H, N—CH3), 3.42 (s, 3H, N—CH3). 13C NMR (DMSO, 100 MHz,) δ 181.3 (C-3′), 162.0, 161.2 (C-4″, C-6″), 159.6 (C-2), 154.7(C-1′), 152.3 (C-9), 151.9 (C-6″), 138.8 (C-4′), 132.7 (C-10′), 131.9, 124.6 (C-2′), 123.6, 122.8 (C—Ar), 89.0 (C-5″), 27.5, 27.3 (N—CH3). ESI-MS (m/z) 388.7 (M+). Anal. Calcd. (C18H13ClN2O6); C, 55.62; H, 3.37, N 7.20; Anal. Found (C18H13ClN2O6): C, 55.94; H, 3.66; N, 6.89.
2.4.4 (2E)-1-(2,4,6-pyrimidinetrione-5-yl)-3-(4-chloro-1-benzopyran-2-one-3-yl)-2-propen-1-one (8d)
Yellow solid, mp >300 °C. IR (KBr) (υmax, cm−1): 3296 (NH), 3071 (NH), 1725 (C⚌O), 1673 (C⚌O), 1648 (C⚌O), 1608 (C⚌C). 1H NMR (DMSO, 400 MHz,) δ 12.63 (s, 2H, NH), 8.31 (1H, d, J = 15.7, Ha), 8.06 (1H, d, J = 15.7, Hb), 8.09–7.40 (4H, m, Ar—H). 13C NMR (DMSO, 100 MHz,) δ 183.9 (C-3′), 162.7, 161.8 (C-4″, C-6″), 161.2 (C-2), 154.7 (C-1′), 152.3 (C-9), 136.9 (C-4), 131.2 (C-10), 131.1, 124.4 (C-2′), 123.3, 122.5 (C—Ar), 85.9 (C-5″). ESI-MS (m/z) 360.7 (M+). Anal. Calcd. (C16H9ClN2O6): C, 53.35; H, 2.51; N 7.76, Anal. Found (C16H9ClN2O6): C, 53.05; H, 2.22; N, 7.45.
2.4.5 (2E)-1-(2-thioxo-4,6-pyrimidinedione-5-yl)-3-(4-chloro-1-benzopyran-2-one-3-yl)-2 propen-1-one (8e)
Orange solid, mp 242–245 °C. IR (KBr) (υmax, cm−1): 3285 (NH), 3209 (NH), 1735 (C⚌O), 1692 (C⚌O), 1664 (C⚌O), 1632 (C⚌C). 1H NMR (DMSO, 400 MHz) δ 12.25 (s, 2H, NH), 8.25 (1H, d, J = 15.6, Ha), 8.07 (1H, d, J = 15.6, Hb), 7.72–7.20 (4H, m, Ar-H). 13C NMR (DMSO, 100 MHz,) δ 183.8 (C-3′), 175.4 (C-2″), 162.8 (C-2), 161.8, 161.2 (C-4″, C-6″), 154.8 (C-1′), 151.8 (C-9), 137.4 (C-4), 131.2 (C-10), 124.2 (C-2′), 131.1 (C-3), 131.5, 123.2, 122.8 (C—Ar), 86.8 (C-5″). ESI-MS (m/z) 376.6 (M+). Anal. Calcd. (C16H9ClN2O5S): C, 51.02; H, 2.40, N 7.43, Anal. Found (C16H9ClN2O5S): C, 50.71; H, 2.70; N, 7.14.
3 Results and discussion
For optimization of reaction conditions the influence of different reaction parameters, such as different catalysts, solvents, supports, the amount of the catalyst employed and temperature on model reaction of 4-chloro-3-formylcoumarin (1) and 3-acetyl-4-hydroxycoumarin (7a) was investigated.
The model reaction was performed in the presence of various supported heterogeneous catalysts including P2O5–SiO2, NaHSO4–SiO2, NH4OAc–SiO2, NH2SO3H–SiO2, xanthan sulfuric acid and HClO4–SiO2 (Table 1). It was observed that the catalytic activity of various heterogeneous catalysts was of the order HClO4–SiO2 > NaHSO4–SiO2 > P2O5–SiO2 > NH2SO3H–SiO2 > xanthan sulfuric acid > NH4OAc–SiO2.
| Entrya | Catalyst | Timeb | Yieldc (%) |
|---|---|---|---|
| 1 | P2O5–SiO2 | 25 min | 69 |
| 2 | NaHSO4–SiO2 | 25 min | 72 |
| 3 | NH4OAc–SiO2 | 1.5 h | 45 (mixture) |
| 4 | NH2SO3H–SiO2 | 45 min | 62 |
| 5 | Xanthan sulfuric acid | 50 min | 42 |
| 6 | HClO4–SiO2 | 10 min | 92 |
To show the superiority of heterogeneous catalyst over acidic and basic catalysts, model reaction was also performed in the presence of different acidic and basic catalysts under solvent-free conditions and it was observed that either the reactions were completed in longer reaction time with lower yield of the products or no reaction occurred (Table 2).
| Entry | Catalyst | Timec | Yieldd (%) |
|---|---|---|---|
| 1a | Fe(NO3)2·9H2O | 5 h | 25 |
| 2a | AlCl3 | 45 min | 42 |
| 3a | Zn(NO3)2 | 5 h | 45 |
| 4a | Zn(CH3COO)2 | 5 h | 51 |
| 5a | PTS | 2 h | 57 |
| 6a | Zn(l-proline)2 | 15 min | 69 |
| 7a | l-proline | 1 h | Trace |
| 8a | ZnCl2 | 40 min | Trace |
| 9a | Zn(l-histidine)2 | 24 h | No reaction |
| 10a | FeCl3·6H2O | 24 h | No reaction |
| 11a | NaOH | 1 h | Trace |
| 12b | Piperidine | 1 h | 68 |
| 13b | Pyridine | 1 h | 62 |
To establish silica as the best support for perchloric acid, other supports were also employed. The model reaction, when carried out in the absence of catalyst no reaction was observed whereas, in the presence of silica gel, reaction was completed in longer time period with lower yield of the product. By the use of other supports such as HClO4–Al2O3 (acidic, basic, neutral), the results were not encouraging (Table 3). Therefore, silica-supported HClO4 was used as catalyst for all reactions.
| Entry | Support | Timeb | Yieldc (%) |
|---|---|---|---|
| 1 | No catalyst | 24 h | No reaction |
| 2 | SiO2 | 24 h | 28 |
| 3 | HClO4 | 24 h | 42 |
| 4 | HClO4–SiO2 | 10 min | 92 |
| 5 | HClO4–alumina (acidic) | 24 h | Incomplete |
| 6 | HClO4–alumina (basic) | 24 h | Incomplete |
| 7 | HClO4–alumina (neutral) | 24 h | Incomplete |
To see the effects of solvents in comparison with the solvent-free condition, the model reaction was carried out in various polar and non-polar solvents (Table 4). Thus, data revealed the solvent-free condition as the best reaction conditions in terms of time and yield.
| Entry | Solvent | Timeb | Yieldc (%) |
|---|---|---|---|
| 1 | CH2Cl2d | 24 h | Traces |
| 2 | CH3CNd | 24 h | Traces |
| 3 | CHCl3d | 24 h | No reaction |
| 4 | THFd | 24 h | No reaction |
| 5 | Waterd | 24 h | No reaction |
| 6 | EtOHd | 12 h | 68 |
| 7 | MeOHd | 12 h | 72 |
| 8 | Isopropanold | 24 h | 65 |
| 9 | Acetic acidd | 45 min | 56 |
| 10 | Solvent-freee | 10 min | 92 |
In order to investigate the effect of amount of catalyst, the model reaction was carried out using different concentrations of the catalyst and the results are shown in Table 5. A blank reaction was carried out using model substrates (1), (7a) at 80 °C and it was found that no reaction had occurred and only starting materials were recovered (entry 1). By carrying out the reaction in HClO4–SiO2 (20 mg), the reaction was again incomplete due to partial conversion of starting materials and/or side product formation (entry 2). By increasing the loading amount to 40, 80 mg of HClO4–SiO2, the rate of reaction progressed steadily and the maximum yield of the product was obtained with catalyst loading of 100 mg (entry 3–5). Thus, optimum amount of catalyst turned out to be 100 mg in order to obtain the best result in terms of yield and time.
To elucidate the effect of the temperature on the reaction rate, model reaction was carried out at different temperatures. At room temperature, only a trace amount of product was obtained. Increase in the reaction temperature affects the reaction rate positively up to 80 °C and further increase could not affect the yield or reaction time (Table 6).
| Entry | Product | Timec (min) | Yieldd (%) |
|---|---|---|---|
| 8a |
|
10 | 92 |
| 8b |
|
20 | 90 |
| 8c |
|
15 | 92 |
| 8d |
|
30 | 90 |
| 8e |
|
25 | 87 |
| 8fb |
|
10 | 92 |
| 8gb |
|
10 | 92 |
| 8hb |
|
10 | 90 |
| 8ib |
|
20 | 91 |
| 8jb |
|
20 | 91 |
Due to exceptional reactivity of formyl group in 4-chloro-3-formylcoumarin (1), our initial efforts were directed toward the catalytic evaluation of HClO4–SiO2 for the synthesis of coumarinyl chalcones (8a–e) by employing (1) and different heterocyclic active methyl compounds (7a–e) in the presence of HClO4–SiO2 under solvent-free heating at 80 °C (Scheme 1). It was observed that the reaction proceeded smoothly, completed in 10–30 min and the product was obtained in excellent yields (87–92%) (Table 7). Encouraged by the remarkable results obtained with the above model reaction conditions, the generality and scope of this new protocol were further demonstrated by synthesizing various coumarinyl chalcones (8f–j) by the reaction of different aldehydes (2–6) and 3-acetyl-4-hydroxycoumarin (7a) under same reaction conditions (Scheme 1). All the reactions proceeded smoothly and the reaction was completed within 10–20 min to afford the products (8f–j) in excellent yields (90–92%) (Table 7). The structure of novel products was deduced from spectral data (IR, 1H NMR, 13C-NMR and MS) and elemental analysis and discussed in experimental section.
The mechanism of the Claisen–Schmidt condensation catalyzed by HClO4–SiO2 catalyst has been shown in Scheme 2. The enol form of 3-acetyl-4-hydroxycoumarin 7a attacks on the catalyst activated 4-chloro-3-formylcoumarin 1 to give intermediate A, which undergoes dehydration to give product 8a (Li et al., 2010).
To show the merit of HClO4–SiO2 under solvent-free conditions in comparison with the reported catalysts for the synthesis of coumarin based chalcones, we also carried out the model reaction with the reported catalysts (Table 8) and the results showed that HClO4–SiO2 was convincingly superior catalyst than other reported catalysts.
| Entry | Catalysts | Solvents | Temperature | Timeb | Yieldc (%) |
|---|---|---|---|---|---|
| 1 | Pyridine | Ethanol | Reflux | 72 h | 65 |
| 2 | HCl (Conc.) | Dioxane | 85 °C | 48 h | 43 |
| 3 | Piperidine | Chloroform | 80 °C | 24 h | No reaction |
| 4 | Piperidine | Butanol | Reflux | 7 h | 54 |
| 5 | Piperidine | Ethanol | Reflux | 8 h | 65 |
| 6 | NaOH | Ethanol | R.T. | 24 h | 56 |
| 7 | NaOH | Ethanol | Reflux | 4 h | 68 |
| 8 | Zn[L(proline)2] | Water | Reflux | 1 h | 79 |
| 9 | HClO4–SiO2 | Solvent-free | 80 °C | 10 min | 92 |
3.1 Reusability of the catalyst
The recovery and reuse of catalysts are highly preferable for heterogeneous catalyst. Therefore, reusability of the catalyst was investigated under solvent-free conditions using model substrates. After completion of the reaction, the mixture was cooled to room temperature, dissolved in ethyl acetate (10 mL) and the catalyst was separated by filtration. The recovered catalyst was washed with ethyl acetate (3 × 10 mL), dried in oven at 100 °C for 3 h and subjected to subsequent cycles. The procedure was repeated and the results indicated that the catalyst could be recycled for four times without any loss of catalytic activity (Table 9).
To check intact morphology of the recovered catalyst after four runs powder XRD and SEM analyses were done (Figs. 5b and 6c). The result referring to the powder XRD showed no obvious changes in structure, in comparison with the fresh catalyst. The SEM observation also showed no significant changes in the morphology of catalyst in comparison with the fresh catalyst.
4 Conclusion
In conclusion, we have developed a convenient, efficient, and environmentally benign protocol for the synthesis of coumarin based chalcones under thermal solvent-free conditions using HClO4–SiO2 as heterogeneous catalyst. The catalyst is easily preparable, stable (up to 500 °C) and can be recycled for four runs without any loss of its catalytic activity. The significant advantages of this clean methodology are excellent yield of the products, shorter reaction time, simple work-up procedure and mild reactions conditions.
Acknowledgments
The author is thankful to Centre of nanotechnology, Department of Applied Physics and University Sophisticated Instrument Facility (USIF), AMU, Aligarh, for providing powder XRD, SEM facilities and SAIF Punjab University, Chandigarh, for providing NMR, Mass spectra.
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