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3,4-dihydroxybenzaldehyde, a natural product isolated and purified from the heartwood of Cassia garrettiana, can scavenge DPPH radical, hydroxyl radical and intracellular ROS.
Synonyms: Catechaldehyde; Protocatechuic aldehyde; NSC 22961
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Pawlak, Mateusz ; Pierzchała, Adam ; Benchimol, Elie ; Tessarolo, Jacopo ; Rebholz, Lukas ; Krstić, Marjan , et al.
Abstract: Circularly polarized luminescence (CPL) in purely organic materials is limited by the almost exclusively electric nature of electronic transitions. Resolving this problem is possible through structuring organic materials at dimensions comparable to the wavelength of visible light. Here, the study explores the use of thin films made of chiral organic nanotubes for the enhanced induction of CPL. The study first performs multi-scale modeling of the chiroptical properties of organic nanotubes using the T-matrix method. Combined with chiroptical measurements, including Mueller matrix polarimetry, the study discusses the chiroptical properties of organic materials within the frames of their multi-scale structuring. When embedding aggregation-induced fluorogens (AIEgens) into the structured films, composites featured with gigantic glum factors reaching ≈10−1 are obtained. Importantly, a series of control experiments is performed to exclude common parasitic effects that can lead to the apparent CPL signals. The enhanced chiroptical properties of the composite films of organic nanotubes and AIEgens enable visual discrimination of their handedness both in the absorption and emission realms. The uncovered multi-mode enhancement of CPL directs future endeavors for anticounterfeiting or holography applications.
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Keywords: aggregation-induced emission ; circular differential scattering ; organic luminophores ; supramolecular nanotubes ; thin films
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CAS No. : | 139-85-5 |
Formula : | C7H6O3 |
M.W : | 138.12 |
SMILES Code : | C1=C(C=CC(=C1O)O)C=O |
Synonyms : |
Catechaldehyde; Protocatechuic aldehyde; NSC 22961
|
MDL No. : | MFCD00003370 |
InChI Key : | IBGBGRVKPALMCQ-UHFFFAOYSA-N |
Pubchem ID : | 8768 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With piperidine; pyridine; at 20℃; | General procedure: The Meldrum?s acid (3.6g, 25mmol) was added into toluene (50ml), then added alcohol or phenol (25mmol). The mixture was heated and refluxed for 5 hrs. When the mixture was cooled to room temperature, added substituted benzaldehyde (10mmol), pyridine (2.5ml) and piperidine (0.25ml). The stirring continued at room temperature, using TLC to trace the reaction until the reaction completely finished. The solvents were distilled out in vacuum; the residue was dissolved in diethyl ether (about 30ml), washed with saturated solution of sodium bicarbonate two times (20ml×2), then diluted hydrochloride acid and distilled water, respectively. The ether phase was driedby anhydrous MgSO4 overnight. After removal of the drier, the solvent was distilled out to get crude solid. (If the crude product was oil, dissolved in dichloromethane (10ml) and then was subjected to chromatograph on a silica gel column (15 g), eluted with ethyl acetate and petroleum ether 1:15. The eluted fraction was distilled outto get crude product. ) The crude solid was recrystallized from a mixture of benzene and diethyl ether (8:2) to afford pure product. | |
270 g | With piperidine; In pyridine; toluene; at 95℃; for 15h; | Add 1L of toluene to the 3L reaction flask,SM1 (cyclopropane (isopropyl) isopropyl ester, 240 g, commercially available) was added in succession under mechanical stirringAnd SM2 (phenylethanol, 202 g, commercially available),After the addition,Warm up to 100C to start timingStop the reaction after 8 hoursCool naturally to cool down to room temperatureSM3 (3,4-dihydroxybenzaldehyde, 160 g, commercially available) was added while stirring was continued.Then add pyridine 166ml and piperidine 17ml,Then it warms up to an internal temperature of 95C.The reaction was stopped after 15 hours of reaction.Cool down to room temperatureAfter adding 1 L of ethyl acetate, the organic phase was washed successively with 1 L of 1M hydrochloric acid solution and 1 L of saturated saline, and the organic phase was dried over anhydrous sodium sulfate for 30 minutes, filtered, and the organic solvent was evaporated in vacuo to obtain a crude product. 2L n-hexane was filtered after beatingThe cake was vacuum dried in a box at 40C for 24 hours to give 270 g of a product of caffeic acid phenylethyl ester. |
General procedure: The desired amount of malonic acid mono esters (0.6 mmol, 1.2 equiv.) was dissolved in toluene (1 mL) followed by the addition of pyridine (12.5 mmol, 25 equiv., 1 mL) and piperidine (0.80 mmol, 1.6 equiv., 79 muL). This mixture was stirred at r.t. for 10 min to form enolates before the desired aldehyde (0.5 mmol,1.0 equiv.) was added at 0C. The reaction mixture was continued to bestirred at r.t. for 1?6 days. TLC was used to monitor the reaction progress. Once the reaction was complete, the reaction mixture was transferred to a separatory funnel using EtOAc (15 mL) and washed with 5% HCl (10 mL×2) and distilled water (10 mL×2). After removalof the ethyl acetate by rotatory evaporation, the crude product was purified by automated flash chromatography, eluting with an ethylacetate/hexanes or methanol/methylene chloride gradient to afford the desired products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39.5% | With potassium carbonate; In hexane; ethyl acetate; N,N-dimethyl-formamide; | Step 1 3,4-Bis(difluoromethoxy)benzaldehyde A suspension of 3,4-dihydroxybenzaldehyde (6.9 g, 50 mmol) and powdered potassium carbonate (13.8 g, 100 mmol) in N,N-dimethylformamide (400 mL) was cooled to -45~C. Chlorodifluoromethane was bubbled into the mixture until 19 g had been dissolved (219 mmol). A dry ice condenser was installed and the temperature was raised gradually to 85? C., and kept at that temperature for 16 hours. After cooling to room temperature, the mixture was carefully diluted with water (600 mL) and extracted 4 times with ether, the extracts were washed 3 times with brine, dried and evaporated. The residue was chromatographed on silica gel, eluding with a 1:3 mixture of ethyl acetate and hexane, to afford the desired product as a colorless liquid (4.7 g, 39.5%). 1 H NMR (400 MHz, acetone-d6) d 7.13 (t, large J, 1H); 7.20 (t, large J, 1H); 7.58 (d, 1H); 7.87 (s, 1H); 7.93 (d, 1H); 10.04 (s, 1H). |
38% | With potassium carbonate; In N-methyl-acetamide; | 2a. 3,4-Bisdifluoromethoxybenzaldehyde A vigorously stirred mixture of 3,4-dihydroxybenzaldehyde (40 g, 290 mmol) and powdered potassium carbonate (120 g, 870 mol) in dimethylformamide (500 mL) was heated under an atmosphere of chlorodifluoromethane at 80 C. for 7 h and then was stirred at room temperature overnight. The mixture was diluted with ether and was filtered. The filtrate was concentrated under reduced pressure, the residue was partitioned between ether and aqueous potassium carbonate and was extracted five times with ether. The organic extract was washed with aqueous potassium carbonate and dried (potassium carbonate). The solvent was removed in vacuo and the residue was purified by flash chromatography, eluding with 4;1 hexanes/ether, to provide an oil (26.2 g, 38%). |
38% | With potassium carbonate; In N-methyl-acetamide; | 2a. 3,4-Bisdifluoromethoxybenzaldehyde A vigorously stirred mixture of 3,4-dihydroxybenzaldehyde (40 g, 290 mmol) and potassium carbonate (120 g, 870 mol) in dimethylformamide (500 mL) was heated under an atmosphere of chlorodifluoromethane at 80 C. for 7 h and then was stirred at room temperature overnight. The mixture was diluted with ether and was filtered. The filtrate was concentrated under reduced pressure, the residue was partitioned between ether and aqueous potassium carbonate and was extracted five times with ether. The organic extract was washed with aqueous potassium carbonate and dried (potassium carbonate). The solvent was removed in vacuo and the residue was purified by flash chromatography, eluding with 4:1 hexanes/ether to provide an oil (26.2 g, 38%). |
3,4-Dihydroxybenzaldehyde (20 g, 0.144 mol) and potassium carbonate (40 g, 0.2898 mol) were taken up in dry DMF (1 L) and cooled to -78C. A Dewar condenser was fitted and freon gas (CHCIF2) was passed through the reaction mixture for 1 h. The reaction mixture was stirred at 85C overnight. Solvent was evaporated under reduced pressure and the residue purified by column chromatography over silica gel (using petroleum ether in ethyl acetate as eluent) to yield the sub-title compound as a pale yellow liquid. Yield: 11 g. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To a solution of the compound 3, 4-DIHYDROXY BENZALDEHYDE (commercially available) (0.072 mole) in dimethylformamide (70 mL), BENZYLTRIETHYL ammonium chloride (0.036 mole) was added. To the resulting reaction mixture was added sodium hydroxide solution (0.0018 mole of 30% solution) dropwise for about 3 minutes with a continuous flow of chloro- difluoro methane. The reaction mixture was acidified with dilute hydrochloric acid and diluted with water. The reaction mixture was extracted with ethyl acetate, washed with saturated solution of sodium chloride and concentrated under reduced pressure. The residue thus obtained was purified by column chromatography to furnish the title compounds. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | [00434] To a solution of 3,4-dihydroxybenzaldehyde (300 mg, 2.2mmol) in DMF (9.0 mL) and H2O (1.0 mL) was added sodium chlorodifluoroacetate (1.33 g) and K2CO3 (729 mg). The mixture was heated up to 100C for 2 h before cooling down to rt. Concentrated HCl (1.54 mL) and H2O (2.0 mL) were added and the reaction was stirred overnight. The mixture was neutralized with IN NaOH to pH > 9, extracted with EtOAc, washed with brine, dried over MgS O4 and concentrated. The crude product was purified by silica gel chromatography to give 132 A (470 mg, 90% yield). 1H NMR (400 MHz, CDCl3) delta ppm 6.29 - 6.89 (m, 2 H) 7.42 (d, J=8.35 Hz, 1 H) 7.66 - 7.90 (m, 2 H) 9.95 (s, 1 H). | |
65% | With potassium carbonate; In water; N,N-dimethyl-formamide; at 80℃; for 16h; | Sodium chlorodifluoroacetate (88 g, 58mmol) was added to a suspension of 3,4-dihydroxybenzaldehyde (11) (20 g, 14 mmol), potassiumcarbonate (80 g, 58 mmol) and water (10 mL, 58 mmol) in DMF (200 mL). Thesuspension was heated to 80 C for 16h and then cooled to rt and diluted with water. The aqueous phase was extractedwith EtOAc and the combined organic fractions were washed with water, brine,dried and concentrated. The residue was partially purified by columnchromatography, eluting with 5-10% EtOAc/petrol to give 3,4-bis(difluoromethoxy)benzaldehyde(22.5 g, 65%) as a colourless oil; deltaH (400 MHz, CDCl3)6.60 (t, J = 72 Hz, 1H, OCHF2), 6.64 (t, J = 72 Hz, 1H, OCHF2), 7.42 (d, J5,6= 8.0 Hz, 1H, H5), 7.76-7.78 (m,2H, H2, H6), 9.96 (s, 1H, CHO); deltaC(125 MHz, CDCl3) 115.2 (t, J= 259 Hz), 115.4 (t, J = 259 Hz),121.5, 122.2, 128.5, 134.2, 142.4, 147.0 189.7; nmax 794, 1038, 1381, 1509, 1698, cm-1.The 3,4-bis(difluoromethoxy)benzaldehyde coeluted with approximately 10-20%unidentified colourless oil: deltaH (400 MHz, CDCl3) 7.13 (s,1H), 7.19 (d, J = 8.0 Hz, 1H), 7.30(s, 1H), 7.59 (d, J = 1.5 Hz, 1H), 7.61(dd, J = 1.5 Hz, 8.0 Hz, 1H), 9.91(s, 1H). |
EXAMPLE 103 ,4-Bis(difluoromethoxy)benzaldehyde ( 10-2) In a sealed tube 3,4-dihydroxybenzaldehyde (10-1, 750 mg, 5.43 mmol, 1.0 equiv), sodium chlorodifluoroacetate (3310 mg, 21.7 mmol, 4 equiv), and potassium carbonate (1800 mg, 13.03 mmol, 2.4 equiv) were suspended in DMF (24.4 mL) and water (2.7 mL). The reaction mixture was stirred at 100 C for 4 hours and was cooled to ambient temperature. HCl (6 N, 10 mL) and water (30 mL) were added and the reaction stirred for an additional 2 hours. NaOH (5 N, aq.) was added until a pH of 10 was obtained. The mixture was extracted withMTBE (3x, 50 mL), dried over MgSO4 and concentrated to afford the desired product (10-2). 1H NMR (CDCl3, 400 MHz) ? 9.97 (s, 1H), 7.76-7.79 (m, 2H), 7.43 (d, J=8.1Hz, 1H), 6.64 (t, J=73.8 Hz, 1H), 6.60 (t, J=73.8 Hz, 1H). |
3,4-Bis(difluoromethoxy)benzaldehyde (4-2)In a sealed tube 3,4-dihydroxybenzaldehyde (4-1, 750 mg, 5.43 mmol, 1.0 equiv), sodium chlorodifluoroacetate (3310 mg, 21.7 mmol, 4 equiv), and potassium carbonate (1800 mg, 13.03 mmol, 2.4 equiv) were suspended in DMF (24.4 mL) and water (2.7 mL). The reaction mixture was stirred at 100 C. for 4 hours and was cooled to ambient temperature. HCl (6 N, 10 mL) and water (30 mL) were added and the reaction stirred for an additional 2 hours. NaOH (5 N, aq.) was added until a pH of 10 was obtained. The mixture was extracted with MTBE (3×, 50 mL), dried over MgSO4 and concentrated to afford the desired product (4-2). 1H NMR (CDCl3, 400 MHz) delta 9.97 (s, 1H), 7.76-7.79 (m, 2H), 7.43 (d, J=8.1 Hz, 1H), 6.64 (t, J=73.8 Hz, 1H), 6.60 (t, J=73.8 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | In ethanol; | EXAMPLE 1 3,4-Dihydroxybenzylidene malononitrile To 11 g (80 mmol) of 3,4-dihydroxybenzaldehyde and 5.5 g (83 mmol) of malononitrile in 40 ml of ethanol, 7 drops of piperidine were added and the mixture was heated at 70° C. for 0.5-1 hour and then poured into water. The resulting solid precipitate was separated by filtration to give 12.7 g (86percent yield) of a yellow solid, m.p. 225° C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
13%; 21% | With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; for 16h; | Methyl chlorodifluoroacetate (15.3 mL, 145 mmol) was added to a suspension of 3,4- dihydroxybenzaldehyde (5.0 g, 36 mmol) and potassium carbonate (20.0 g, 145 mmol) in DMF (10 mL). The suspension was heated to 60 0C for 16 h and then diluted with water. The aqueous phase was extracted with EtOAc and the combined organic fractions were washed with saturated aqueous NaHCOs, water, brine, dried and concentrated. The residue was purified by column chromatography, eluting with 10% EtOAc/petrol to give 3,4-bis(difluoromethoxy)benzaldehyde (1.1 g, 13%) as a colourless oil; deltaH (400 MHz, CDCI3) 6.60 (t, J = 72 Hz, 1 H, OCHF2), 6.64 (t, J = 72 Hz, 1 H, OCHF2), 7.42 (d, J5,6 = 8.0 Hz, 1 H, H5), 7.76-7.78 (m, 2H, HZ, H6), 9.96 (s, 1 H, CHO); deltac (125 MHz, CDCI3) 115.2 (t, J = 259 Hz), 1 15.4 (t, J = 259 Hz), 121.5, 122.2, 128.5, 134.2, 142.4, 147.0 189.7; vmax 794, 1038, 1381 , 1509, 1698, cm"1. Further elution provided 4-difluoromethoxy-3-hydroxybenzaldehyde (1.43 g, 21 %) as a colourless crystalline solid; mp 94-95 0C (recrystallized from EtOAc); deltaH (500 MHz, CDCI3) 5.82 (s, 1 H, OH), 6.65 (t, J = 72.0 Hz, 1 H, CHF2), 7.27 (d, J5,6 = 8.0 Hz, 1 H, H5), 7.44 (dd, J5,6 = 8.0, J2,6 = 2.0 Hz, 1 H, H6), 7.54 (d, J2,6 = 2.0 Hz, 1 H, HZ), 9.92 (s, 1 H, CHO); deltac (125 MHz, CDCI3) 115.6 (t, J = 259 Hz), 117.1 , 119.2, 123.1 , 134.6, 142.9, 147.8, 190.9; vmax 1087, 1237, 1508, 1592, 1686, 2859, 3313 cm"1. |
13%; 21% | With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; for 16h; | Methyl chlorodifluoroacetate (15.3 mL, 145mmol) was added to a suspension of 3,4-dihydroxybenzaldehyde (11) (5.0 g, 36 mmol) and potassiumcarbonate (20.0 g, 145 mmol) in DMF (10 mL). The suspension was heated to 60 C for 16 h and then diluted with water. The aqueous phase wasextracted with EtOAc and the combined organic fractions were washed withsaturated aqueous NaHCO3, water, brine, dried and concentrated. Theresidue was purified by column chromatography, eluting with 10% EtOAc/petrol togive 3,4-bis(difluoromethoxy)benzaldehyde (1.1 g, 13%) as a colourless oil; deltaH(400 MHz, CDCl3) 6.60 (t, J= 72 Hz, 1H, OCHF2), 6.64(t, J = 72 Hz, 1H, OCHF2), 7.42 (d, J5,6 = 8.0 Hz, 1H, H5), 7.76-7.78 (m, 2H, H2, H6),9.96 (s, 1H, CHO); deltaC (125MHz, CDCl3) 115.2 (t, J =259 Hz), 115.4 (t, J = 259 Hz),121.5, 122.2, 128.5, 134.2, 142.4, 147.0 189.7; nmax 794, 1038, 1381, 1509, 1698, cm-1.Further elution provided 4-difluoromethoxy-3-hydroxybenzaldehyde (1.43 g, 21%)as a colourless crystalline solid; mp 94-95 C (recrystallized from EtOAc); deltaH (500 MHz, CDCl3)5.82 (s, 1H, OH), 6.65 (t, J = 72.0 Hz, 1H, CHF2), 7.27 (d, J5,6= 8.0 Hz, 1H, H5), 7.44 (dd, J5,6 = 8.0, J2,6 = 2.0 Hz, 1H, H6), 7.54 (d, J2,6 = 2.0 Hz, 1H, H2),9.92 (s, 1H, CHO); deltaC (125MHz, CDCl3) 115.6 (t, J =259 Hz), 117.1, 119.2, 123.1, 134.6, 142.9, 147.8, 190.9; nmax 1087, 1237, 1508, 1592, 1686,2859, 3313 cm-1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With acetic acid; In ethanol; at 80℃; for 0.166667h;Microwave irradiation; | General procedure: 2-(2-Arylidenehydrazino)-6-fluorobenzothiazoles 6a-r. General Procedure D. A mixture of compound 2 (0.0549 g, 0.0003 mol), the appropriate aromatic aldehyde (0.00033 mol) and glacial acetic acid (0.1 mL) in ethanol (5 mL) was heated under microwave (20 W) at 80 °C for 10 min. On cooling, the precipitated solid was collected by filtration, washed with water, dried and crystallized from the appropriate solvent to give the desired compounds 6a-r. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
9.5 mg; 38.9 mg; 32.08 mg; 227.3 mg | With sodium hydrogencarbonate; In water; at 180℃; for 1.0h;pH 4.0; | The salvianolic acid B (Fig. 3) was formulated with NaHCO3 water at pH 4.0 to prepare 40 mg / mL of salvianolic acid B solution,The solution was placed in a 50 mL subcritical water stainless steel reactor. After the furnace reached 180 C and stabilized, the reaction vessel was placed in a heating furnace and started to stand. 60min after the rapid removal of the reactor and into the ice bath cooling, the liquid removed, freeze-dried, rich in salvianolic acid A crude (Figure 4). 2. High-speed countercurrent chromatography separation purification salvianolic acid A The solvent system is petroleum ether: ethyl acetate: n-butanol: water=2:3: 1:9, add on 10 mm trifluoroacetic acid as stationary phase, down to 10 mm ammonia-water as the mobile phase, the high speed countercurrent chromatograph column volume is 300 ml, type quantity on 1.2g, speed 800 rpm, relative to stationary phase, down as the mobile phase, flow rate 2.0 ml/min, stationary phase retention rate of 57%, detection wavelength 280 nm. Specific operation steps are: according to the above-mentioned solvent proportion solvent system, arranged in the separatory funnel, layered after shaking, to balance after a period of time on the two-phase separated under, on adds together 10 mm trifluoroacetic acid as stationary phase, down to 10 mm ammonia-water as the mobile phase, taking 1.2g salvianolic acid A crude product rich in, dissolved in 5 ml plus 10 mm relative to the trifluoroacetic acid and 5 ml of in not ammonia down for use. Shanghai tauto Company is researching the semi-preparative high-speed countercurrent chromatograph, it is composed of a plunger pump, a sample introduction valve, ultraviolet detector, recorder and the chromatographic separation column (by the polytetrafluoroethylene tube multi-layer which is formed by winding of the spiral pipe, capacity of 300 ml) and the like, first of all make the sampling valve is in a sampling state, the fixed phase is pumped to a certain velocity of fully a chromatographic separation column, stop the pump. The opening of the speed controller, the high-speed flow chromatograph chromatographic separation column is rotary, speed up to 800 rpm when, the dissolved sample injector for injection counter current chromatograph injection valve the liquid storage tube, rotating sampling valve is the post state, the sample enter the chromatographic separation column. A mobile phase flow rate is 2.0 ml/min, mobile phase starts the pump, then according to the detector ultraviolet light (Figure 2) the spectrogram of the target component, shall be Radix Salviae Miltiorrhizae element (38.9 mg, Figure 5), salvianolic acid D (9.5 mg, Figure 6), salvianolic acid A (227.3 mg, Figure 7) and protocatechualdehyde (32.8 mg, Figure 8), HPLC analysis for the purity of 98% or more. The use of high performance liquid chromatography analysis isolate, liquid chromatography conditions: Kromasil 100 - 5C18 Column (4.6 × 250 mm), ultraviolet detection wavelength 286 nm, column temperature: 25 C, flow rate: 1.0 ml/min, the sample: 10muL, mobile phase using acetonitrile (A) and 0.2% formic acid aqueous solution (B) gradient elution, gradient conditions are as follows: 0 - 9min, 10% -22% A; 9 - 19min, 22% -24% A; 19 - 35min, 24% A; 35 - 43min, 24% -36% A; 43 - 48min, 36% -100% A; 48 - 50min, 100% A. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
803 mg | Weigh the content of 95% <strong>[520-26-3]hesperidin</strong> 1.5 g,200 muL of tetrahydropyrrole was added,DMSO 4.0 mL dissolved, add 150 mul of glacial acetic acid, stirring at 60 C for 3 h, then adding 3,4-hydroxybenzaldehyde 0.25 g, 8h plus finished, continue to react for 3h, adding silica gel,Eluting with a chloroform-methanol gradient to give 803 mg of a yellow powder of 3- (3,4-hydroxyphenylmethyl) -anthropin (cpd 2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With indium(III) chloride; In ethanol; at 120℃; for 0.166667h;Microwave irradiation; | General procedure: A mixture of <strong>[1004-38-2]2,4,6-triaminopyrimidine</strong> 1 (1.0 mmol), 3-(2-cyanoacetyl)indole 2 (1.0 mmol), appropriate aromatic aldehyde (1.0 mmol) and indium chloride (0.05 mmol) in ethanol (5.0 mL) were subjected to microwave irradiation for 10 min at 120 C. After completion of the reaction (monitored by TLC using a dichloromethane-ethanol (9:1) mixture as the mobile phase), the reaction mixture was cooled and filtered. The solid product obtained was initially washed with ethanol, and finally recrystallized from ethanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | In N,N-dimethyl-formamide; at 90.0℃; for 8.0h; | (2) Add the above-mentioned trimesic hydrazide (5.0g, 0.02mol) and 3,4-dihydroxybenzaldehyde (8.21g, 0.06mol) into a 250mL flask containing 100mL DMF, magnetically at 90C The reaction was stirred for 8 hours, dispersed into a beaker containing a large amount of water while hot, filtered with suction and washed with ethanol three times, and dried under vacuum at 0.06MPa and below 60C to obtain a pure yellow powdery Zn2+ probe compound. The calculated yield was 96%. |