CN115233243A - Preparation method of 2,4, 5-trisubstituted oxazole derivative under electrocatalysis - Google Patents
Preparation method of 2,4, 5-trisubstituted oxazole derivative under electrocatalysis Download PDFInfo
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Abstract
The invention discloses a preparation method of 2,4, 5-trisubstituted oxazole derivatives under electrocatalysis, which belongs to the technical field of organic synthesis, and the preparation method comprises the steps of adding alkynylamide derivatives, selenide compounds, electrolytes and nitrile solvents into a reactor, and promoting the reaction to be carried out through an electrocatalysis strategy; after the reaction is finished, concentrating by using a rotary evaporator to obtain a crude product, and then carrying out silica gel column chromatography separation to obtain a target product. The invention has the advantages of green and environment-friendly synthesis method, simple method, quick reaction and the like.
Description
Technical Field
The invention belongs to the technical field of organic synthesis, and particularly relates to a preparation method of a 2,4, 5-trisubstituted oxazole derivative under electrocatalysis.
Background
The oxazole compounds not only occupy a great position in the fields of organic chemical synthesis and natural drug synthesis, but also have wide application in the field of medicines. For example, oxazole drugs are commercially available and clinically used in the fields of nervous system diseases, infectious diseases, cardiovascular and cerebrovascular diseases, endocrine and metabolic diseases, and the like (as shown in fig. 1). Therefore, how to synthesize oxazole compounds efficiently and greenly is always a focus of attention in the fields of biology, chemistry and pharmacy, and is a hot topic of research in the field of organic synthesis.
Among a plurality of oxazole compounds, phenyl oxazole has been favored by researchers for its wide application. The research finds that the synthetic method of the phenyl oxazole compound mainly comprises the following steps: (1) Under the catalysis of ligand and transition metal, heterocycle and iodobenzene synthesize corresponding phenyl oxazole compound; (2) Under the catalysis of noble metal, the oxazole derivatives react with phenylalkynoic acid to generate corresponding phenyl oxazole compounds; (3) Under the catalysis of transition metal, oxazole derivatives react with phenyl sulfide to generate corresponding phenyl oxazole compounds; (4) PAR-2Hg with transition metal as catalyst 2+ The compound is used as a halogen ion chemical sensor, and oxazole derivatives react with halogen benzene to generate corresponding phenyl oxazoles. In summary, the existing methods for synthesizing phenyl oxazole compounds are more; most of these methods, however, require the use of expensive metal catalysts and complex ligands, even more highly contaminating compounds. From an environmental point of view, the above synthesis method is not a green and efficient synthesis method.
Therefore, how to develop a method which is green, nontoxic and simple to operate by using cheap and easily available reagents so as to obtain the phenyl oxazole compound with high conversion rate is a very challenging and urgent problem to be solved.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provide a synthesis method of a 2,4, 5-trisubstituted oxazole compound with green, high efficiency and low cost, and the method can prepare and obtain a target product with high selectivity and high yield under electrocatalysis. In addition, the reaction operation process is simple, the complex operation of no water and no oxygen is not needed, and meanwhile, the use of a noble metal catalyst is avoided, so that the method is convenient for industrial application and production.
The invention adopts the following technical scheme:
a preparation method of 2,4, 5-trisubstituted oxazole derivatives under electrocatalysis comprises the steps of mixing acetylenic amide derivatives, selenide compounds, electrolytes and nitrile solvents, and then carrying out electrocatalysis reaction to obtain the 2,4, 5-trisubstituted oxazole derivatives.
In the invention, the structural formula of the alkynylamide derivative is shown as a formula (I) or a formula (I-1):
the structural formula of the nitrile solvent is shown as a formula (II)
The structural formula of the selenide compound is shown as the formulas (III) and (IV):
the structural formula of the 2,4, 5-trisubstituted oxazole derivative is shown as a formula (V) or a formula (V-1)
The reaction is schematically as follows:
in the present invention, R 1 Is H, halogen, alkoxy or alkyl; r 2 Is an alkyl group; r 3 Is an alkyl group; r 4 Is hydrogen, halogen or haloalkyl; r 5 Is a substituted or unsubstituted naphthyl, benzyl or alkyl group.
Preferably, R 1 Is H, halogen, methoxy, tert-butyl, C 1 ~C 6 An alkyl group.
Preferably, R 2 Is tert-butyl, cyclobutyl, adamantyl, cyclohexyl, n-butyl, C 1 -C 6 An alkyl group.
Preferably, R 3 Alkyl groups such as methyl, ethyl and propyl.
Preferably, R 4 Hydrogen, halogen, trifluoromethyl, and the like.
Preferably, R 5 Is a substituted or unsubstituted naphthyl, benzyl or C 1 ~C 6 An alkyl group.
In the present invention, the reaction time is 0.5 to 4 hours, preferably 1 hour.
In the invention, the certain temperature is 0-40 ℃, and preferably, the temperature is room temperature.
In the present invention, the electrolyte is tetrabutylammonium tetrafluoroborate.
In the invention, the usage ratio of the alkyne amide derivative, the selenide compound, the nitrile solvent and the electrolyte is 0.3 mmol (0.01-0.06 mmol) to (3-10 mL) to (0.1-0.5 mmol), preferably, the usage ratio of the alkyne amide derivative, the selenide compound, the nitrile solvent and the electrolyte is 0.3 mmol to 0.03 mmol to 6 mL to 0.3 mmol. Based on the existing research background and combined with the requirement of green chemical production, the invention creates a preparation method for efficiently synthesizing the phenyl oxazole derivatives under electrocatalysis, the method does not need to use metal catalysts and alkali, the reaction conditions are mild and green, and the preparation method can be enlarged to gram-scale.
In the present invention, the organic solvent is used as both the solvent and the reactant. The nitrile is any one of nitrile compounds such as acetonitrile, propionitrile, butyronitrile, isobutyronitrile, decylonitrile and benzonitrile, and the solvent is preferably acetonitrile, so that various raw materials can be converted into the product with high conversion rate.
Compared with the prior art, the invention has the beneficial effects that: the reaction overcomes the defects of the prior art, and provides a synthesis method of a 2,4, 5-trisubstituted oxazole compound with green, high efficiency and low cost, thereby avoiding the use of expensive transition metal salts. In addition, the reaction does not need any metal catalyst and alkali, the operation process is simple, the complex operation of no water and no oxygen is not needed, the target product can be prepared with high selectivity and high yield in the air atmosphere, and the possibility is provided for the industrial synthesis application of the compounds.
Drawings
FIG. 1 is a structural schematic diagram of a conventional oxazole-based drug;
FIG. 2 is a schematic view of a trifurcate reaction flask;
FIG. 3 is a NMR spectrum of the product obtained in example;
FIG. 4 is a NMR carbon spectrum of the product obtained in example.
Detailed Description
The invention adds alkynylamine compounds shown in formula (I), selenoether shown in formula (IV) or (III), nitrile solvent shown in formula (II) and electrolyte into a trifurcate reaction bottle (shown in figure 2), and the reaction bottle is stirred for reaction under the conditions of certain temperature and air atmosphere. The reaction progress is monitored by TLC or GC until the raw materials react completely, and the 2,4, 5-trisubstituted oxazole compound (V) is obtained by post-treatment. Optional post-processing procedures include: filtering, mixing the sample with silica gel, and finally performing column chromatography purification to obtain a corresponding 2,4, 5-trisubstituted oxazole compound, wherein the column chromatography purification is a commonly used technical means in the field; the yield is an isolated yield.
The present invention will be described in further detail with reference to specific examples, but the present invention is not limited thereto. The experimental methods described in the following examples are all conventional methods unless otherwise specified; the reagents and starting materials, if not otherwise specified, are commercially available and/or may be prepared according to known methods. The water used in the reaction comes from the solvent, and the acetonitrile brand of the solvent of the example is GENERAL-REAGENT, G80988B, and is directly used.
The alkynylamide derivative of the invention can be conveniently prepared by a coupling method through corresponding commercial aryl acetylene bromine compounds and N-alkyl p-toluenesulfonamide, and the formula is as follows:
example 1
To a trifurcated reaction flask were added the alkynylamide I-1 (0.3 mmol) of formula 1, diphenyldiselenide (10 mol%), electrolyte (tetrabutylammonium tetrafluoroborate, 0.3 mmol) and acetonitrile II-1 (6.0 mL). Inserting a carbon cloth electrode into a reaction tube, electrifying (10 mA), conventionally stirring for 1h at room temperature under an air atmosphere, after the reaction is finished, spin-drying the solvent by using a rotary evaporator, then adding 10 mL of ethyl acetate into the reaction system for extraction, washing an organic phase by using a saturated sodium chloride solution, drying by using anhydrous sodium sulfate, filtering, concentrating under reduced pressure to remove the solvent, and separating the residue by using column chromatography, wherein the elution solvent is: ethyl acetate/petroleum ether to give product V-1 (81% yield), with reference to fig. 3 and 4: 1 H NMR (400 MHz, CDCl 3 ) δ 7.95 – 7.93 (m, 2H), 7.77 (d, J = 8.4 Hz, 2H), 7.44 (t, J = 7.6 Hz, 2H), 7.32 (d, J = 7.9 Hz, 3H), 3.10 (s, 3H), 2.44 (d, J = 2.5 Hz, 6H). 13 C NMR (101 MHz, CDCl 3 ) δ 158.44, 145.58, 144.07, 134.55, 133.39, 129.61, 128.81, 128.72, 128.70, 127.22, 125.21, 37.25, 21.74, 14.38.
example 2
The amount of diphenyl diselenide was increased to 20 mol%, and the yield of the target product I-1 was 83% under the same conditions as in example 1.
Example 3
The reaction time was extended to 2 hours and the other conditions were the same as in example 1 to give the desired product I-1 in a yield of 76%.
Example 4
The carbon cloth electrodes (CC) of the cathode and the anode are changed into platinum sheet electrodes, and the rest conditions are the same as those of the example 1, so that the yield of the target product I-1 is 73 percent.
Example 5
The target product I-1 was obtained by reducing the amount of acetonitrile to 10 equivalents (about 0.093 mL) and using DCM (6 mL) as solvent under the same conditions as in example 1.
Example 6
The current was reduced to 3 mA, and the yield of the target product I-1 was 46% under the same conditions as in example 1.
Example 7
0.3 mmol hexafluoroisopropanol was added as an additive to the reaction system under the same conditions as in example 1, and the yield of the objective product I-1 was 72%.
Example 8
The diphenyl diselenide was changed to 3-fluorodiphenyl diselenide, and the yield of the target product I-1 was 68% under the same conditions as in example 1.
As can be seen from the above examples 1-8, the best catalyst is the reaction conditions of example 1, i.e. the electrode is carbon cloth-Carbon Cloth (CC), the current is 10mA, the catalyst is diphenyl diselenide, the reaction time is 1 hour, and the temperature is room temperature. And further selects different substituted alkynylamide and nitrile derivatives as substrates to develop a high-efficiency preparation method of the 2,4, 5-trisubstituted oxazole derivative.
Example 9
To a trifurcated reaction flask was added the alkynylamide I-2 of formula 2 (0.3 mmol), diphenyldiselenide (10 mol%), electrolyte (tetrabutylammonium tetrafluoroborate, 0.3 mmol) and acetonitrile II-1 (6.0 mL). Inserting an electrode into a reaction tube, electrifying (10 mA), stirring at room temperature for 1h under an air atmosphere, after the reaction is finished, spin-drying the solvent by using a rotary evaporator, then adding 10 mL of ethyl acetate into the reaction system for extraction, washing an organic phase by using a saturated sodium chloride solution, drying by using anhydrous sodium sulfate, filtering, concentrating under reduced pressure to remove the solvent, and separating the residue by using column chromatography, wherein the eluting solvent is: ethyl acetate/petroleum ether to give product V-2 (68% yield).
1 H NMR (400 MHz, CDCl 3 ) δ 7.65 (d, J = 8.3 Hz, 2H), 7.55 – 7.53 (m, 1H), 7.33 – 7.29 (m, 1H), 7.26 – 7.24 (m, 4H), 3.08 (s, 3H), 2.45 (s, 3H), 2.41 (s, 3H), 2.36 (s, 3H). 13 C NMR (101 MHz, CDCl 3 ) δ 159.08, 146.12, 143.85, 137.19, 134.73, 134.53, 130.75, 129.80, 129.52, 128.39, 126.75, 125.95, 37.13, 21.72, 20.68, 14.46.
Example 10
To a trifurcated reaction flask was added an alkynylamide I-3 of formula 3 (0.3 mmol), diphenyldiselenide (10 mol%), electrolyte (tetrabutylammonium tetrafluoroborate, 0.3 mmol) and acetonitrile II-1 (6.0 mL). Inserting an electrode into a reaction tube, electrifying (10 mA), stirring for 1h under an air atmosphere, after the reaction is finished, spin-drying the solvent by using a rotary evaporator, then adding 10 mL of ethyl acetate into the reaction system for extraction, washing an organic phase by using a saturated sodium chloride solution, drying by using anhydrous sodium sulfate, filtering, concentrating under reduced pressure to remove the solvent, and separating the residue by using column chromatography, wherein the elution solvent is: ethyl acetate/petroleum ether to give product V-3 (72% yield).
1 H NMR (400 MHz, CDCl 3 ) δ 7.76 (dd, J = 8.5, 1.9 Hz, 3H), 7.69 (s, 1H), 7.33 (t, J = 7.6 Hz, 3H), 7.15 (d, J = 7.6 Hz, 1H), 3.09 (s, 3H), 2.44 (d, J = 2.4 Hz, 6H), 2.40 (s, 3H). 13 C NMR (101 MHz, CDCl 3 ) δ 158.36, 145.72, 144.04, 138.40, 134.63, 133.23, 129.62, 129.58, 128.78, 128.68, 127.11, 125.71, 122.48, 37.25, 21.77, 21.72, 14.42.
Example 11
To a trifurcated reaction flask was added an alkynylamide I-4 of formula 4 (0.3 mmol), diphenyldiselenide (10 mol%), electrolyte (tetrabutylammonium tetrafluoroborate, 0.3 mmol) and acetonitrile II-1 (6.0 mL). Inserting an electrode into a reaction tube, electrifying (10 mA), stirring for 1h under an air atmosphere, after the reaction is finished, spin-drying the solvent by using a rotary evaporator, then adding 10 mL of ethyl acetate into the reaction system for extraction, washing an organic phase by using a saturated sodium chloride solution, drying by using anhydrous sodium sulfate, filtering, concentrating under reduced pressure to remove the solvent, and separating the residue by using column chromatography, wherein the elution solvent is: ethyl acetate/petroleum ether to give product V-4 (77% yield).
1 H NMR (400 MHz, CDCl 3 ) δ 7.81 (d, J = 8.7 Hz, 2H), 7.73 (d, J = 8.1 Hz, 2H), 7.56 (d, J = 8.6 Hz, 2H), 7.32 (d, J = 8.0 Hz, 2H), 3.08 (s, 3H), 2.44 (d, J = 2.9 Hz, 6H). 13 C NMR (101 MHz, CDCl 3 ) δ 158.73, 144.71, 144.24, 134.27, 133.89, 132.01, 129.66, 128.69, 126.73, 126.19, 122.78, 37.22, 21.78, 14.40.
Example 12
To a trifurcated reaction flask was added an alkynylamide I-5 of formula 5 (0.3 mmol), diphenyldiselenide (10 mol%), electrolyte (tetrabutylammonium tetrafluoroborate, 0.3 mmol) and acetonitrile II-1 (6.0 mL). Inserting an electrode into a reaction tube, electrifying (10 mA), stirring for 1h under an air atmosphere, after the reaction is finished, spin-drying the solvent by using a rotary evaporator, then adding 10 mL of ethyl acetate into the reaction system for extraction, washing an organic phase by using a saturated sodium chloride solution, drying by using anhydrous sodium sulfate, filtering, concentrating under reduced pressure to remove the solvent, and separating the residue by using column chromatography, wherein the elution solvent is: ethyl acetate/petroleum ether to give product V-5 (69% yield).
1 H NMR (400 MHz, CDCl 3 ) δ 7.94 (ddd, J = 8.3, 5.2, 2.6 Hz, 2H), 7.75 – 7.73 (m, 2H), 7.33 (d, J = 8.0 Hz, 2H), 7.14 (td, J = 8.9, 2.6 Hz, 2H), 3.09 (d, J = 2.7 Hz, 3H), 2.44 (d, J = 2.9 Hz, 6H). 13 C NMR (101 MHz, CDCl 3 ) δ 162.82 (d, J = 249.2 Hz), 158.38, 144.91, 144.20, 134.36, 133.06, 129.66, 128.72, 127.29 (d, J = 8.4 Hz), 123.59 (d, J = 3.5 Hz), 115.95 (d, J = 21.9 Hz), 37.26, 21.76, 14.35.
19 F NMR (377 MHz, CDCl 3 ) δ -111.80.
Example 13
To a trifurcated reaction flask was added an alkynylamide I-6 of formula 6 (0.3 mmol), diphenyldiselenide (10 mol%), electrolyte (tetrabutylammonium tetrafluoroborate, 0.3 mmol) and acetonitrile II-1 (6.0 mL). Inserting an electrode into a reaction tube, electrifying (10 mA), stirring for 1h under an air atmosphere, after the reaction is finished, spin-drying the solvent by using a rotary evaporator, then adding 10 mL of ethyl acetate into the reaction system for extraction, washing an organic phase by using a saturated sodium chloride solution, drying by using anhydrous sodium sulfate, filtering, concentrating under reduced pressure to remove the solvent, and separating the residue by using column chromatography, wherein the elution solvent is: ethyl acetate/petroleum ether to give product V-6 (74% yield).
1 H NMR (400 MHz, CDCl 3 ) δ 7.87 (d, J = 8.5 Hz, 2H), 7.77 (d, J = 8.2 Hz, 2H), 7.46 (d, J = 8.5 Hz, 2H), 7.32 (d, J = 8.0 Hz, 2H), 3.09 (s, 3H), 2.44 (s, 6H), 1.34 (s, 9H). 13 C NMR (101 MHz, CDCl 3 ) δ 158.17, 151.88, 145.86, 144.04, 134.62, 132.79, 129.64, 128.73, 125.81, 124.96, 124.41, 37.29, 34.88, 31.34, 21.79, 14.43.
Example 14
To a trifurcated reaction flask was added an alkynylamide I-7 of formula 7 (0.3 mmol), diphenyldiselenide (10 mol%), electrolyte (tetrabutylammonium tetrafluoroborate, 0.3 mmol) and acetonitrile II-1 (6.0 mL). Inserting an electrode into a reaction tube, electrifying (10 mA), stirring for 1h under an air atmosphere, after the reaction is finished, spin-drying the solvent by using a rotary evaporator, then adding 10 mL of ethyl acetate into the reaction system for extraction, washing an organic phase by using a saturated sodium chloride solution, drying by using anhydrous sodium sulfate, filtering, concentrating under reduced pressure to remove the solvent, and separating the residue by using column chromatography, wherein the elution solvent is: ethyl acetate/petroleum ether to give product V-7 (75% yield).
1 H NMR (400 MHz, CDCl 3 ) δ 7.88 – 7.84 (m, 2H), 7.76 (d, J = 8.3 Hz, 2H), 7.31 (d, J = 8.0 Hz, 2H), 6.97 – 6.93 (m, 2H), 4.07 (q, J = 7.0 Hz, 2H), 3.08 (s, 3H), 2.43 (s, 3H), 2.41 (s, 3H). 13 C NMR (101 MHz, CDCl 3 ) δ 159.23, 157.62, 145.71, 143.94, 134.48, 131.66, 129.52, 128.62, 126.72, 119.75, 114.68, 63.52, 37.20, 21.67, 14.83, 14.27.
Example 15
To a trifurcated reaction flask was added an alkynylamide I-8 (0.3 mmol) of formula 8, diphenyldiselenide (10 mol%), electrolyte (tetrabutylammonium tetrafluoroborate, 0.3 mmol) and acetonitrile II-1 (6.0 mL). Inserting an electrode into a reaction tube, electrifying (10 mA), stirring for 1h under an air atmosphere, after the reaction is finished, spin-drying the solvent by using a rotary evaporator, then adding 10 mL of ethyl acetate into the reaction system for extraction, washing an organic phase by using a saturated sodium chloride solution, drying by using anhydrous sodium sulfate, filtering, concentrating under reduced pressure to remove the solvent, and separating the residue by using column chromatography, wherein the elution solvent is: ethyl acetate/petroleum ether to give product V-8 (57% yield).
1 H NMR (400 MHz, CDCl 3 ) δ 7.89 (d, J = 7.3 Hz, 2H), 7.42 (t, J = 7.5 Hz, 2H), 7.33 (t, J = 7.4 Hz, 1H), 3.25 (s, 3H), 3.13 (s, 3H), 2.50 (s, 3H). 13 C NMR (101 MHz, CDCl 3 ) δ 158.87, 145.45, 133.19, 128.93, 128.90, 126.97, 125.19, 37.96, 37.01, 14.47.
Example 16
To a trifurcated reaction flask was added an alkynylamide I-9 of formula 9 (0.3 mmol), diphenyldiselenide (10 mol%), electrolyte (tetrabutylammonium tetrafluoroborate, 0.3 mmol) and acetonitrile II-1 (6.0 mL). Inserting an electrode into a reaction tube, electrifying (10 mA), stirring for 1h under an air atmosphere, after the reaction is finished, spin-drying the solvent by using a rotary evaporator, then adding 10 mL of ethyl acetate into the reaction system for extraction, washing an organic phase by using a saturated sodium chloride solution, drying by using anhydrous sodium sulfate, filtering, concentrating under reduced pressure to remove the solvent, and separating the residue by using column chromatography, wherein the elution solvent is: ethyl acetate/petroleum ether to give product V-9 (71% yield).
1 H NMR (400 MHz, CDCl 3 ) δ 8.11 (dd, J = 7.1, 0.6 Hz, 2H), 7.35 (ddd, J = 8.3, 7.2, 1.3 Hz, 2H), 7.30 – 7.23 (m, 4H), 7.22 – 7.16 (m, 5H), 2.62 (s, 3H). 13 C NMR (101 MHz, CDCl 3 ) δ 159.86, 143.92, 140.16, 129.95, 128.88, 128.50, 127.00, 126.33, 124.75, 124.23, 120.74, 120.45, 110.95, 14.59.
The invention aims to overcome the defects of the prior art and provide a green, efficient and low-cost synthesis method of a polysubstituted oxazole compound, and the method can prepare a target product with high selectivity and high yield under electrocatalysis. In addition, the reaction operation process is simple, the complex operation of no water and no oxygen is not needed, and meanwhile, the use of a noble metal catalyst is avoided, so that the method is convenient for industrial application and production. The embodiments described above are only preferred embodiments of the present invention and are not exhaustive of the possible implementations of the present invention. Any obvious modifications to the above would be obvious to those of ordinary skill in the art, but would not bring the invention so modified beyond the spirit and scope of the present invention.
Claims (10)
1. A preparation method of 2,4, 5-trisubstituted oxazole derivatives under electrocatalysis is characterized by comprising the following steps: mixing the alkynylamide derivative, the selenide compound, the electrolyte and the nitrile solvent, and then carrying out electrocatalytic reaction to obtain the 2,4, 5-trisubstituted oxazole derivative.
2. The method for preparing 2,4, 5-trisubstituted oxazole derivatives under electrocatalysis according to claim 1, wherein the ratio of the amounts of the acetylenic amide derivatives, the selenoether compounds and the nitrile solvents is 0.3 mmol (0.01-0.06 mmol) to (3-10 mL).
3. The electrocatalytic preparation method of 2,4, 5-trisubstituted oxazole derivatives according to claim 1, wherein the electrocatalytic reaction is carried out at a temperature of 0 to 40 ℃ for a time of 0.5 to 4 hours.
4. The method for preparing 2,4, 5-trisubstituted oxazole derivatives under electrocatalysis according to claim 1, wherein the nitrile solvent is one or more of acetonitrile, propionitrile, butyronitrile, isobutyronitrile, decanonitrile and benzonitrile.
5. The electrocatalytic preparation method of 2,4, 5-trisubstituted oxazole derivative according to claim 1, wherein the structural formula of said alkynylamide derivative is represented by formula (I) or formula (I-1):
the structural formula of the nitrile solvent is shown as a formula (II)
The structural formula of the selenide compound is shown as the formulas (III) and (IV):
the structural formula of the 2,4, 5-trisubstituted oxazole derivative is shown as a formula (V) or a formula (V-1)
In general formula (I), formula (I-1), (II), (III), (IV), (V) and formula (V-1): r is 1 Is H, halogen, alkoxy or alkyl; r 2 Is an alkyl group; r is 3 Is an alkyl group; r is 4 Is hydrogen, halogen or haloalkyl; r is 5 Is a substituted or unsubstituted naphthyl, benzyl or alkyl group.
6. The method for preparing 2,4, 5-trisubstituted oxazole derivatives under electrocatalysis according to claim 5, wherein R is 1 Is H, halogen, methoxy, tert-butyl or C 1 ~C 6 An alkyl group; r 2 Is tert-butyl, cyclobutyl, adamantyl, cyclohexyl, n-butyl or C 1 -C 6 An alkyl group; r is 3 Is methyl, ethyl or propyl; r 4 Is hydrogen, halogen or trifluoromethyl; r 5 Is a substituted or unsubstituted naphthyl, benzyl or C 1 ~C 6 An alkyl group.
7. The electrocatalytic process for the preparation of a 2,4, 5-trisubstituted oxazole derivative according to claim 1 wherein said electrolyte is tetrabutylammonium tetrafluoroborate.
8. The electrocatalytic process for the preparation of 2,4, 5-trisubstituted oxazole derivative according to claim 1 wherein the electrocatalytic reaction is carried out in air.
9. A 2,4, 5-trisubstituted oxazole derivative prepared by the electrocatalytic preparation method of a 2,4, 5-trisubstituted oxazole derivative according to claim 1.
10. The application of the mixture of the alkynylamide derivative, the selenide compound, the electrolyte and the nitrile solvent in preparing the 2,4, 5-trisubstituted oxazole derivative through electrocatalytic reaction.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115466975A (en) * | 2022-11-02 | 2022-12-13 | 淮北师范大学 | Synthetic method of 2-methyl-4-aryl-5-xanthene oxazole compound |
| CN117418243A (en) * | 2023-10-19 | 2024-01-19 | 上海陶术生物科技有限公司 | Method for synthesizing selenized pyrimido [1,2-b ] indazole derivative based on electrochemical method and application |
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2022
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115466975A (en) * | 2022-11-02 | 2022-12-13 | 淮北师范大学 | Synthetic method of 2-methyl-4-aryl-5-xanthene oxazole compound |
| CN117418243A (en) * | 2023-10-19 | 2024-01-19 | 上海陶术生物科技有限公司 | Method for synthesizing selenized pyrimido [1,2-b ] indazole derivative based on electrochemical method and application |
| CN117418243B (en) * | 2023-10-19 | 2024-09-24 | 上海陶术生物科技有限公司 | Method for synthesizing selenized pyrimido [1,2-b ] indazole derivative based on electrochemical method and application |
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