A cost-effective and convenient procedure for the synthesis of silica-supported 1-(2-sulfooxy)ethyl)1 H-pyridine-1-ium- chloride SiO /[SEP]Cl as a recoverable heterogeneous and Brønsted acid catalyst is described, and was used for the one-pot synthesis of aryl-14H-dibenzo[a,j]xanthenes under solvent- and metal-free conditions at 110 °C in short reaction time with a yield of up to 95%. The present method offers several advantages such as simplicity in operation, ease of preparation and recycling of Brønsted acidic ionic liquid (BAIL), solvent-free reaction conditions, and no hazardous organic solvents are used in the entire procedure including workup and purification. Graphical abstract OSO H Cl OH Ar Ar-CH2O 3a-p up to yield 95% solvent-free, 110 C No need to column chromatography No hazardous organic solvent Simple purification Solvent-free Keywords 1-(2-Sulfooxy)ethyl)1H-pyridine-1-ium-chloride · One-pot reaction · 14-Aryl-14H-dibenzo[a,j]xanthene · Solvent- and metal-free conditions · Brønsted acidic ionic liquid Introduction * Sami Sajjadifar firstname.lastname@example.org Recently ionic liquids (ILs) are considered as dual reagents (catalysts and solvents) and a greener alternative for a range Department of Chemistry, Payame Noor University, P.O. of various organic reactions, but the application of them as Box 19395-4697, Tehran, Iran Vol.:(0123456789) 1 3 98 Applied Petrochemical Research (2018) 8:97–105 catalyst in the absence of solvent is vital and important in polytungstozincate acid . Although several of these pro- organic and inorganic chemistry . As well as, ILs are an cedures suffer from disadvantages such as the use of excess appropriate alternative instead of volatile and toxic organic reagents/catalysts, tedious workup procedures, toxicity of solvents in the future due to high polarity, solubility with the reagent, unsatisfactory yields, low yields of products, use certain organic solvents and/or water, low vapor pressure, of organic solvents, prolonged reaction time, use of the often and excellent solubility in organic and inorganic materials expensive catalysts and non-recyclability, the focus on intro- . On the other hand, ILs have been frequently used as ducing efficient, economical, and solvent-free procedures solar cell, catalysts, biocatalysts, in nanomaterial synthesis, with high activity, simple reaction workup, and reusability liquid–liquid separations, polymerization reactions, extrac- of the catalyst to overcome these problems is still in demand tion, dissolution processes, electrochemistry and electro- for the synthesis of xanthene derivatives. deposition, and as supercapacitors [3–10]. It is necessary to introduce milder, simple reaction Among organic compounds, the synthesis of xanthene workup, solvent- and metal-free, faster, reusability of the and its derivatives has received specific attention among catalyst, and generally a greener approach accompanied pharmacological activities and organic chemists due to hav- with higher yields for the synthesis of xanthene derivatives. ing a wide range of biological and therapeutic properties Therefore, and according to the above-mentioned notes, it such as antioxidant , cytotoxic , anti-proliferative seems that silica-supported 1-(2-sulfooxy)ethyl)1H-pyri- , antifungal , anti-inflammatory, antiviral , and dine-1-ium-chloride SiO /[SEP]Cl as a catalyst can be an antibacterial properties . Furthermore, xanthene and its appropriate in the synthesis of these organic compounds. derivatives would be used in laser technologies , as pH- In this research, we wish to report a rapid and cost- sensitive fluorescent materials for visualization of biomol- effective procedure for the synthesis of silica-supported ecules , sensitisers in dye-sensitized solar cells (DSSCs) 1-(2-sulfooxy)ethyl)1H-pyridine-1-ium-chloride SiO /[SEP] , in photodynamic therapy , as hole-transporting Cl as a new, highly efficient, and Brønsted acid catalyst for materials in organic light-emitting devices (OLEDs) , the preparation of 14-aryl-14H-dibenzo[a,j]xanthene 3a–p and in the food industry as additives . Xanthene and derivatives under solvent-, metal-free and thermal conditions its derivatives are available in natural plants [23, 24]. For (Scheme 2). instance, examples of natural xanthenes are 3-isopropyl- 9a-methyl-1,2,4a,9a-tetrahydroxanthene A, used as an anti- dote for all snake venoms, blumeaxanthene B and lumeax- Experimental anthene C, used to treat gynecological disorders (Scheme 1). Different procedures have been employed for the prepara - General tion of xanthenes and benzoxanthenes [25–29]. In addition, one of the best, easiest, and cost-effective procedures for the All of the reagents used in the current study were purchased synthesis of xanthene derivatives is condensation between from Merck, Aldrich, and Fluka and used without further aldehydes with 2-naphthols under different conditions in the purification. All the products are known compounds and presence of various Lewis and Brønsted acid catalysts such were characterized by comparing the IR (KBr), H NMR, as Fe (SO ) H O , polyvinylpolypyrrolidone-bound and C NMR spectroscopic data and their melting point to 2 4 3.7 2 boron trifluoride , pentafluorophenyl ammonium triflate the literature values. Nuclear magnetic resonance ( H NMR 2+ 13 , silica sulfuric acid , γ-Fe O –HAp–Fe NPs , and C NMR) was recorded in CDCl solvent on a Bruker 2 3 3 H PW V O , cellulose sulfuric acid , Yb(OTf) DRX-300 and -400 spectrometer using tetramethylsilane 5 10 2 40 3 , 2,6-Pyridinedicarboxylic acid , silica-supported (TMS) as an internal reference. IR spectra were recorded [2-(sulfooxy)ethyl]sulfamic acid , Selectfluor™ [ 40], on a Frontier FT-IR (PerkinElmer) spectrometer using a KBr carbon-based solid acid , I , ZnO NPs , p-tol- disk. The purities of the substrates and reaction monitoring uenesulfonic acid/ionic liquid , trityl chloride , and were accomplished by TLC on silica gel PolyGram SILG/ Scheme 1 Examples of natural xanthenes B C 1 3 Applied Petrochemical Research (2018) 8:97–105 99 Scheme 2 One-pot synthesis of xanthene derivatives in the pres- ence of BAIL under solvent-free conditions 1 13 UV 254 plates. Melting points (MP) were determined on a comparing the melting point, H NMR and C NMR spectra Thermo Scientific 9300 melting point apparatus. with those reported in the literature. Preparation of silica‑supported 1‑(2‑sulfooxy) 14‑(4‑Bromophenyl)‑14H‑dibenzo[a,j]xanthenes ethyl)1H‑pyridine‑1‑ium‑chloride SiO /[SEP]Cl (Table 4, entry 3e) In this study, silica-supported 1-(2-sulfooxy)ethyl)1H-pyr- HNMR (300 MHz, CDCl ): δ 5.34 (1H, s, CH), 6.16–6.48 idine-1-ium-chloride SiO /[SEP]Cl as a BAIL catalyst was (10H, m, Ar–H), 6.68–6.75 (4H, m, Ar–H), 7.19–7.22 (2H, prepared according to the literature procedure (Fig. 1) . m, J = 7.8, Ar–H). CNMR (75 MHz, CDCl ): δ 37.46, Spectral data of 1-(2-sulfooxy)ethyl)1H-pyridine-1-ium- 116.65, 118.01, 120.21, 122.39, 124.37, 126.92, 128.91, chloride are as follows: viscous brown oil: IR (KBr): OH 129.11, 129.88, 131.04, 131.24, 131.58, 143.98, 148.67. −1 −1 −1 (3200–3600 cm ), C=N (1658 cm ), C=C (1426 cm ), −1 −1 1 S=O (1232 cm ), and S–O (614 cm ). H NMR (400 MHz, 4‑(4‑Methoxyphenyl)‑14H‑dibenzo[a,j]xanthenes DMSO-d ): δ 3.13–3.16 (t, J = 5.6 Hz, 2H), 3.93–3.970 (t, (Table 4, entry 3 g) J = 8 Hz, 2H), 8.10–8.17 (t, J = 12 Hz, 2H), 8.61 (s, 1H), 13 1 8.92–8.99 (t, J = 6.4 Hz, 2H), 9.00–9.42 (d, 1H). C NMR H NMR (300 MHz, CDCl ): 2.49 (3H, s, OMe), 5.36 (1H, (100 MHz, DMSO-d ): 60.7, 61.8, 128.2, 142.2, 146.0. s, CH), 5.59–5.61 (2H, d, J = 8.66 Hz, Ar–H), 6.32–6.45 (6H, m, Ar–H), 6.49–6.55 (2H, m, Ar–H), 6.69–6.76 (4H, General procedure for the preparation m, Ar–H), 7.31–7.33 (2H, d, J = 8.48, Ar–H); C NMR of 14‑aryl‑14H‑dibenzo[a,j]xanthenes(75 MHz, CDCl ): 37.17, 55.05, 113.89, 117.58, 118.06, 122.77, 124.28, 126.81, 128.80, 128.87, 129.23, 131.13, A mixture of 2-naphthol (1 mmol), various aldehydes 131.47, 137.45, 148.69, 157.89. (1 mmol) and SiO /[SEP]Cl (20 mol%) in a 10-mL round- bottomed flask connected to a reflux condenser was stirred 14‑(2‑Chlorophenyl)‑14H‑dibenzo[a,j]xanthenes in an oil bath at 110 °C. Completion of the reaction was (Table 4, entry 3 l) indicated by TLC (monitored by TLC, ethylacetate:n-hex- ane 1:3). After completion, the solvent was removed under HNMR (300 MHz, CDCl ): δ 5.69 (1H, s, CH), 5.81–5.82 reduced pressure and the crude product was recrystallized (2H, d, Ar–H), 6.27–6.40 (5H, m, Ar–H), 6.50 (2H, d, with ethanol to afford the pure product in 81–95% yield. All Ar–H), 6.55–6.67 (4H, m, Ar–H), 7.63–7.66 (2H, J = 8.5, d, the products were known compounds and characterized by Ar–H). CNMR (75 MHz, CDCl ): δ 34.63, 118.02, 118.11, Fig. 1 Pictures of reaction between pyridine and 2-chlo- roethanol (a), 1-(2-sulfooxy) ethyl)1H-pyridine-1-ium-chlo- ride (b), and silica-supported 1-(2-sulfooxy)ethyl)1H-pyri- dine-1-ium-chloride (c) 1 3 100 Applied Petrochemical Research (2018) 8:97–105 1 13 123.46, 124.44, 126.93, 127.87–127.94, 128.66, 129.08, H and C NMR spectra of the BAIL C are presented in 129.60, 130.13, 130.89, 131.76, 131.81, 143.57, 148.95. Figs. 3 and 4. The important peaks of H NMR spectrum of BAIL C were related to the acidic hydrogen (SO H) which was observed in 8.61 ppm. The C NMR spectrum of the Results and discussion BAIL C exhibited five signals in agreement with the pro- posed structure. For this work, BAIL C as a green and reusable catalyst was The activity of the new BAIL C as a reusable and green prepared by condensation reaction between pyridine and catalyst was tested using a one-pot condensation reaction 2-chloroethanol that led to ionic liquid B, following which of various aromatic aldehydes (1 mmol) with 2-naphthol chlorosulfonic acid was added dropwise and slowly to ionic (2 mmol) under solvent-free conditions for the preparation liquid B for 45–60 min at 0 °C, which afforded BAIL C of biologically active 14-aryl-14H-dibenzo[a,j]xanthene (Scheme 3) . derivatives (Scheme 2). The structure of 1-(2-sulfooxy)ethyl)1H-pyridine-1-ium- For this purpose, to optimize the reaction conditions for chloride [SEP]Cl was characterized on the basis of its IR the synthesis of compound 3a, the condensation reaction 1 13 (KBr), H and C NMR data, which were presented in of benzaldehyde (1 mmol) and 2-naphthol (2 mmol) was the “Experimental” section. The characterization of BAIL chosen using different amounts of BAIL as a heterogeneous C in comparison to compounds A and B was further con- and Brønsted acid catalyst under solvent-free conditions at ducted by FT-IR spectrum (Fig. 2). As it can be seen from room temperature (Table 1). As it can be seen in Table 1, −1 Fig. 2, the broad peak is at around 3200–3600 cm which when reaction was carried out in the absence of the catalyst, is related to the OH group. On the other hand, the spectra after 120 min the reaction was without yield (Table 1, entry −1 show that the broad peak is at around 1658 cm for C=N 1). The best results were achieved when 20 mol% of the −1 and 1426 cm for C=C, which imply both are related to BAIL was appropriate to promote the reaction efficiently −1 pyridine ring, and the strong peak at 1232 cm is related to and give the product in excellent yield and in short reaction the stretching vibration of S=O bond. time (Table 1, entry 6). Additionally, it is worth noting that Scheme 3 The synthesis of OH Cl SO H Cl 1-(2-sulfooxy)ethyl)1H-pyri- dine-1-ium-chloride [SEP]Cl HCl 45-60 min Reflux, 24 h N N N Cl 0 C 100-120 C OSO H OH A B C Cl Fig. 2 Comparison of IR spectrum of compounds A and B with BAIL C 1 3 Applied Petrochemical Research (2018) 8:97–105 101 Fig. 3 H NMR spectrum of [SEP]Cl Fig. 4 C NMR spectrum of [SEP]Cl 1 3 102 Applied Petrochemical Research (2018) 8:97–105 Table 1 Result of the amount of the catalyst in the synthesis of com- Table 3 Optimization of various solvents in the synthesis of com- pound 3a under solvent-free conditions pound 3a on the model reaction under reflux condition a a Entry Catalyst loading Reaction time Yield (%) Entry Solvent (5 ml) Reflux condi- Reaction Yield (%) (%) (min) tions (°C) time (min) 1 None 120 – 1 EtOH 78.3 60 44 2 1 100 35 2 MeOH 65 60 40 3 5 90 54 3 CHCl 61.2 60 51 4 10 90 75 4 CH Cl 39.6 60 45 2 2 5 15 45 80 5 EtOAc 77.1 60 30 6 20 20 85 Yield of isolated products 7 25 20 85 Yield of isolated products (containing electron-withdrawing, electron-donating groups, and halogens on their aromatic ring) were reacted with when a higher percentage of loading of the BAIL was used, 2-naphthol in the optimal reaction conditions to produce the the yields did not improve (Table 2, entry 6). desired products 3a–p in excellent yields and in short reac- To optimize the temperatures, the condensation of benza- tion time (Table 4). As it can be seen in Table 4, in all cases, ldehyde (1 mmol) and 2-naphthol (2 mmol) in the presence aromatic aldehydes 3a–p containing both electron-donating of 20 mol% of BAIL was checked, and the results are tabu- and electron-withdrawing groups (–NO , –Me, –OMe, –Br, lated in Table 2. As it can be seen in Table 2, temperature –Cl, –OH, –NR ) reacted with 2-naphthol under solvent-free increase was appropriate for the synthesis of compound 3a. conditions at 110 °C for an appropriate time (10–30 min) Therefore, the model reaction in solvent-free conditions at and good to excellent yields (81–95%) to generate 14-aryl- 110 °C leads to the highest yield (94%) and shortest reaction 14H-dibenzo[a,j]xanthene derivatives. time (15 min) compared to the other temperatures. The recovery and reusability of the catalyst is a very In the next study, to compare the efficiency of solvent- important factor in industry and green chemistry, and also free conditions versus solvent conditions, the condensation one of the advantages of heterogeneous catalyst. It is also reaction between benzaldehyde (1 mmol) and 2-naphthol worth noting that silica-supported 1-(2-sulfooxy)ethyl)1H- (2 mmol) using BAIL (20 mol%) was tested in various sol-pyridine-1-ium-chloride SiO /[SEP]Cl as a catalyst can be vents such as ethanol, methanol, chloroform, dichlorometh- recovered at the end of the reaction and can be used six ane, and ethyl acetate under reflux conditions, and the results times without losing its activity (Fig. 5). The yields of are summarized in Table 3. As it can be seen in Table 3, low 4-(4-nitrophenyl)-14H-dibenzo[a,j]xanthenes 3i obtained yields of the product and longer reaction time rather than after 15 min include 95, 93, 93, 91, 91 and 88%, respectively. solvent-free conditions were obtained. Hence, performing The advantages of BAIL were compared (solvent, cata- the reaction under solvent-free conditions and in the pres- lyst loading, time, yield, and temperature) with some other ence of 20 mol% of BAIL at 110 °C was determined as the catalysts for the synthesis of compound 3a from the reaction optimal condition. between benzaldehyde with 2-naphthol, and the results are To assess the efficiency and the scope of BAIL for the represented in Table 5. In 2012, Rao et al. (Table 5, entry synthesis of biologically active 14-aryl-14H-dibenzo[a,j] 3) reported the preparation of 14-aryl-14H-dibenzo[a,j] xanthene derivatives, a variety of aromatic aldehydes xanthenes using ZnO NPs; in this procedure, the yield of products are low (80%) and reaction time is long (60 min). On the other hand, this procedure needs high temperature (150 °C) to complete the reaction. In 2008, Khaksar et al. Table 2 Optimization of temperature in the synthesis of compound 3a under solvent-free conditions (Table 5, entry 5) reported a highly efficient method for a the synthesis of 14-aryl(alkyl)-14H-dibenzo[a,j]xanthenes Entry Temperature (°C) Reaction time Yield (%) using pentafluorophenyl ammonium triflate (PFPAT); this (min) method relies on the use of toxic solvent like toluene, and 1 60 55 81 requires very long reaction time (4.5 h). In addition, one of 2 80 40 87 the other problems is that the catalyst used in this method 3 100 30 94 is non-recyclable. Recently, Kumara et al. in 2006 reported 4 110 15 94 the use of Selectfluor™ (Table 5, entry 7) as a catalyst for 5 120 20 94 the preparation of 14-aryl(alkyl)-14H-dibenzo[a,j]xan- thene derivatives in which the reaction completion time Yield of isolated products 1 3 Applied Petrochemical Research (2018) 8:97–105 103 Table 4 The solvent-free a b Entry Aldehydes Time (min) Yield (%) M.p. °C (Lit) synthesis of biologically active 14-aryl-14H-dibenzo[a,j] Found Reported xanthene derivatives using 3a C H 15 94 188–190 191–193  silica supported 1-(2-sulfooxy) 6 5 ethyl)1H-pyridine-1-ium- 3b 2-NO C H 30 84 308–310 309–311  2 6 4 chloride 3c 3-NO C H 30 89 211–213 210–212  2 6 4 3d 3-OCH C H 12 90 261–263 260–262  3 6 4 3e 4-BrC H 25 94 295–296 294–295  6 4 3f 4-CH C H 20 88 225–227 226–228  3 6 4 C H 15 85 201–203 203–205  3g 4-OCH 3 6 4 3h 4-ClC H 10 93 282–284 285–287  6 4 3i 4-NO C H 20 95 309–311 310–312  2 6 4 3j 3-OHC H 25 84 171–173 169–171  6 4 3k 4-OHC H 22 87 140–141 1387–139  6 4 3l 2-ClC H 17 85 221 219–220  6 4 3m 2,4-ClC H 13 95 86–88 87–89  6 3 3n 4-C H C H 30 81 279–281 281–283  6 5 6 4 3o 2,3-ClC H 15 94 220–222 221–224  6 3 3p 4-N,N-(CH ) C H 30 90 222–224 224–226  3 2 6 4 Reactions were run till the completion as indicated by TLC Yield of isolated products Fig. 5 Recyclability of the Recovery of the catalyst SiO /[SEP]Cl for the synthesis of compound 3i after 15 min Time (min) Yield (%) was very long and tedious (8 h), and also requires high tem- Conclusion perature (125 °C). Wang et al. in 2009 reported the use of iodine (Table 5, entry 9) as a catalyst for the synthesis of In summary, silica-supported 1-(2-sulfooxy)ethyl)1H- 14-aryl(alkyl)-14H-dibenzo[a,j]xanthene derivatives under pyridine-1-ium-chloride SiO /[SEP]Cl as a new and neat conditions; one of the main problems of this method recoverable heterogeneous catalyst was employed for the is the use of iodine, which is toxic and biodegradable, and synthesis of 14-aryl-14H-dibenzo[a,j]xanthene derivatives the reaction time is long. As it can be seen in Table 5, the by the one-pot condensation reaction of various aldehydes reaction in the presence of BAIL was simpler, solvent free, with 2-naphthol under thermal and solvent-free conditions. economical, eco-friendly, the catalyst used was recyclable, This methodology offers very attractive features such as and the reaction time was shorter. On the whole, it seems economic viability of catalyst, short reaction time, high that this catalytic system can be an appropriate alternative yield of products, operational simplicity, easier workup method for the synthesis. 1 3 104 Applied Petrochemical Research (2018) 8:97–105 Table 5 Comparison of various Entry Reaction condition Time (h) Yield (%) Refs. catalysts used for the synthesis of compound 3a b 1 Silica sulfuric acid (0.05 g)/solvent free/125 °C 20 90  2 Yb(OTf) /[BPy]BF (0.01 mmol)/110 °C 7 89  3 4 3 ZnO NPs (0.3 mmol)/solvent free/150 °C 60 80  4 PVPP-BF /solvent free (0.05 g)/120 °C 1.5 94  5 PFPAT (10 mol%)/toluene/25–30 °C 4.5 90  6 H PW V O (0.5 mol%)/solvent-free/100 °C 1 67  5 10 2 40 7 Selectfluor™ (0.1 m mol)/neat conditions/125 °C 8 93  8 Polytungstozincate acid (0.05 g)/solvent free/80 °C 1 81  9 Iodine (0.1 mmol)/neat conditions/90 °C 2.5 90  10 SiO /[SEP]Cl (20 mol%)/solvent free/110 °C 15 94 – Yield of isolated products In minute Metathesis Polymerization (ROMP) in ionic liquids: scope and procedure, ease of recovering and reusing of the catalyst, limitations. 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Applied Petrochemical Research – Springer Journals
Published: Apr 2, 2018
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