CN114276311B - Method for synthesizing aryl oxazole compound by using nickel complex as catalyst - Google Patents
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Abstract
The invention relates to a method for synthesizing an aryl oxazole compound by using a nickel complex as a catalyst, which comprises the following steps: taking a nickel complex containing an ortho-position carborane-based benzothiazole structure as a catalyst, taking benzoxazole and halogenated aromatic compounds as raw materials, and carrying out an oxidative coupling reaction at room temperature in the presence of alkali to obtain the aryl oxazole compound. Compared with the prior art, the method utilizes the nickel complex containing the ortho-position carborane-based benzothiazole structure to efficiently catalyze a multi-component reaction one-pot method to synthesize the aryl oxazole compound at room temperature, so that the aryl oxazole compound is synthesized at room temperature, the catalyst has low use equivalent weight, the reaction condition is mild, the substrate universality is high, the raw materials are cheap and easy to obtain, and the product yield is high.
Description
Technical Field
The invention belongs to the technical field of preparation of aryl oxazole compounds, and relates to a method for synthesizing an aryl oxazole compound by using a nickel complex as a catalyst.
Background
The structural element of the aryl azole exists widely in substances and drug molecules with physiological activity, such as the anti-inflammatory analgesic flurbiprofen has the structure. Among the methods for synthesizing the compounds, the method for catalyzing C-H bond arylation of azole compounds by using transition metals is a simple, efficient and high-atom-economy method. Reaction systems using a noble metal palladium and a rhodium compound as a catalyst have been reported in many cases in this field (chem. Rev.2007,107, 174), but these reaction systems are expensive in catalyst price and require the use of a complex ligand. Subsequent studies have gradually focused on the design synthesis of inexpensive metal catalysts, such as nickel-catalyzed arylation of benzothiazole and benzimidazole (chem.sci.2015, 6,6792 org.lett.2009,11, 1733).
Kalyani et al reported a nickel-catalyzed arylation reaction of benzoxazoles, but this reaction required the use of air-sensitive Ni (COD) 2 The catalyst is a catalyst (J.org.chem.2019, 84, 13092), the catalyst usage equivalent is large, and the reaction temperature is high, and the factors limit the industrial application of the system.
Therefore, it is important to develop a method for catalytically synthesizing an aryl oxazole compound with simplicity, high efficiency and mild reaction conditions.
Disclosure of Invention
The invention aims to provide a method for synthesizing an aryl oxazole compound by using a nickel complex as a catalyst. The nickel complex adopted by the invention is insensitive to air and water, has stable property, shows high-efficiency catalytic activity in the reaction of catalyzing the oxidative coupling of benzoxazole and halogenated aromatic compounds to synthesize the aryl oxazole compounds, and has the advantages of simple and green preparation method, high yield, mild reaction conditions and good universality.
The purpose of the invention can be realized by the following technical scheme:
a method for synthesizing an aryl oxazole compound by using a nickel complex catalyst comprises the following steps: taking a nickel complex containing an ortho-position carborane-based benzothiazole structure as a catalyst, taking benzoxazole and halogenated aromatic compounds as raw materials, and carrying out an oxidative coupling reaction at room temperature in the presence of alkali to obtain an aryloxazole compound; the structural formula of the nickel complex containing the ortho-carborane-based benzothiazole structure is shown as follows:
wherein "·" is a boron hydrogen bond.
Further, the method specifically comprises the following steps: dissolving a nickel complex containing an ortho-position carborane-based benzothiazole structure, benzoxazole, a halogenated aromatic compound and alkali in an organic solvent, reacting at room temperature for 100-300min, and separating and purifying to obtain the aryl oxazole compound.
Further, the halogenated aromatic hydrocarbon compound is one of chlorobenzene, 4-methoxy chlorobenzene, 4-methyl chlorobenzene, 4-cyano chlorobenzene, 2-methyl chlorobenzene and 3-chloropyridine.
Further, the base is potassium carbonate or potassium phosphate.
Further, the organic solvent is toluene.
Furthermore, the molar ratio of the nickel complex containing the ortho-carborane-based benzothiazole structure to the benzoxazole to the halogenated aromatic hydrocarbon compound to the base is (0.001-0.002): 1.1.
Further, the preparation method of the nickel complex containing the ortho-carborane-based benzothiazole structure comprises the following steps:
1) Adding n-BuLi (n-butyllithium) solution to ortho-carborane (o-C) at-80 deg.C to-75 deg.C 2 B 10 H 12 ) Stirring the solution for 25-35min, and reacting at room temperature for 30-60min;
2) Adding bromobenzothiazole, and reacting at room temperature for 6-8h;
3) Adding NiCl 2 Reacting at room temperature for 3-5h, and post-treating to obtain the nickel complex.
Further, in the step 1), the n-BuLi solution is an n-hexane solution of n-BuLi, and the vicinal carborane solution is a tetrahydrofuran solution of vicinal carborane.
Further, in step 3), the post-treatment process is as follows: standing and filtering after the reaction is finished, decompressing and pumping the solvent to obtain a crude product, and then carrying out column chromatography separation on the crude product; in the process of column chromatography separation, an eluent is a mixed solvent of petroleum ether and tetrahydrofuran, and the volume ratio of the petroleum ether to the tetrahydrofuran is (5-10): 1.
Further, the n-BuLi, the ortho-carborane, the bromobenzothiazole and the NiCl 2 The molar ratio of (2.2-3.0) to (1), (0.8-1.2) to (0.8-1.2).
Compared with the prior art, the invention has the following characteristics:
1) According to the invention, the nickel complex containing an ortho-position carborane-based benzothiazole structure is used for efficiently catalyzing a multi-component reaction at room temperature to synthesize the aryl oxazole compound by a one-pot method, so that the synthesis of the aryl oxazole compound at room temperature is realized, the catalyst has low use equivalent, the reaction condition is mild, the substrate universality is high, the raw materials are cheap and easy to obtain, and the product yield is high;
2) The synthesis process of the nickel complex containing the ortho-position carborane-based benzothiazole structure is simple and green, the selectivity and the yield are high, and the prepared nickel complex has stable physical and chemical properties, thermal stability and high catalytic efficiency.
Detailed Description
The present invention will be described in detail with reference to specific examples. The present embodiment is implemented on the premise of the technical solution of the present invention, and a detailed implementation manner and a specific operation process are given, but the scope of the present invention is not limited to the following embodiments.
The invention provides a method for synthesizing an aryl oxazole compound by using a nickel complex as a catalyst, which comprises the following steps: taking a nickel complex containing an ortho-position carborane alkyl benzothiazole structure as a catalyst, taking benzoxazole and halogenated aromatic compounds as raw materials, and carrying out an oxidative coupling reaction at room temperature in the presence of alkali to obtain an aryloxazole compound; the structural formula of the nickel complex containing the ortho-carborane-based benzothiazole structure is shown as follows:
wherein "·" is a boron hydrogen bond.
The method specifically comprises the following steps: dissolving a nickel complex containing an ortho-position carborane-based benzothiazole structure, benzoxazole, a halogenated aromatic compound and alkali in an organic solvent, reacting at room temperature for 100-300min, and separating and purifying to obtain the aryl oxazole compound.
Wherein the halogenated aromatic hydrocarbon compound is one of chlorobenzene, 4-methoxy chlorobenzene, 4-methyl chlorobenzene, 4-cyano chlorobenzene, 2-methyl chlorobenzene and 3-chloropyridine. The base is potassium carbonate or potassium phosphate. The organic solvent is toluene. The molar ratio of the nickel complex containing an ortho-carborane-based benzothiazole structure to the benzoxazole to the halogenated aromatic hydrocarbon compound to the alkali is (0.001-0.002): 1.1.
The preparation method of the nickel complex containing the ortho-carborane-based benzothiazole structure comprises the following steps:
1) Adding the n-BuLi solution into the ortho-carborane solution at a temperature of between 80 ℃ below zero and 75 ℃ below zero, stirring and reacting at room temperature for 30 to 60min;
2) Adding bromobenzothiazole, and reacting at room temperature for 6-8h;
3) Adding NiCl 2 Reacting at room temperature for 3-5h, and carrying out post-treatment to obtain the nickel complex.
In the step 1), the n-BuLi solution is n-hexane solution of n-BuLi, and the ortho-carborane solution is tetrahydrofuran solution of ortho-carborane.
In the step 3), the post-treatment process is as follows: standing and filtering after the reaction is finished, decompressing and pumping out the solvent to obtain a crude product, and then carrying out column chromatography separation on the crude product; in the process of column chromatography separation, an eluent is a mixed solvent of petroleum ether and tetrahydrofuran, and the volume ratio of the petroleum ether to the tetrahydrofuran is (5-10): 1.
n-BuLi, ortho-carborane, bromobenzothiazole, niCl 2 The molar ratio of (2.2-3.0) to (1), (0.8-1.2) to (0.8-1.2).
Example 1:
synthesizing a nickel complex containing an ortho-carborane-based benzothiazole structure:
slowly dropwise adding n-BuLi in n-hexane (1.6 mmol) to o-C containing ortho-carborane at-78 deg.C 2 B 10 H 12 (0.64 mmol) in tetrahydrofuran, stirred at this temperature for 30 minutes, slowly warmed to room temperature and allowed to continue to react for 1 hour, after which bromobenzothiazole (0.64 mmol) was added and allowed to continue to react at room temperature for 6 hours. Then adding NiCl 2 (0.64 mmol) was added to the reaction system and reacted for another 3 hours. After the reaction is finished, standing and filtering, decompressing and draining the solvent, and performing column chromatography separation on the obtained crude product (according to the volume ratio, petroleum ether/tetrahydrofuran =6: 1) to obtain a brown target product, namely the nickel complex containing the ortho-carborane-based benzothiazole structure (yield 78%), wherein the reaction formula is as follows:
wherein "·" represents a boron hydrogen bond B-H.
1 H NMR(400MHz,CDCl 3 ,25℃):δ＝7.96(d,J＝7.0Hz,1H),7.66(t,J＝7.0Hz,1H),7.52 (d, J =7.0Hz, 1H), 7.30 (t, J =7.0Hz, 1H) 9 B 10 H 14 ClNiNS: c29.17, H3.81, N3.78; experimental values: c29.22, H3.86 and N3.70.
Example 2:
the nickel complex is used for catalyzing and synthesizing the aryl oxazole compound, and the specific process is as follows:
using the nickel complex prepared in example 1 as a catalyst, dissolving the nickel complex (0.001 mmol), benzoxazole (1.0 mmol), chlorobenzene (1.1 mmol) and potassium carbonate (1.2 mmol) in 2mL of toluene, reacting at room temperature for 100 minutes, concentrating the reaction solution after the reaction is finished, directly separating by silica gel column chromatography, and drying until the mass is unchanged to obtain the corresponding product C 13 H 9 NO (90% yield), reaction formula:
1 H NMR(400MHz,CDCl 3 ) δ:8.12 (d, J =8.0hz, 2h), 7.44 (s, 1H), 7.36 (d, J =8.0hz, 1h), 7.10-7.01 (m, 5H). HRMS theoretical value C 13 H 9 NO(M) + :195.0684, actual measurements: 195.0688.
example 3:
the nickel complex is used for catalyzing and synthesizing the aryl oxazole compound, and the specific process is as follows:
using the nickel complex prepared in example 1 as a catalyst, dissolving nickel complex (0.0015 mmol), benzoxazole (1.0 mmol), 4-methoxychlorobenzene (1.1 mmol) and potassium carbonate (1.2 mmol) in 2mL of toluene, reacting at room temperature for 200 minutes, concentrating the reaction solution after the reaction is finished, directly separating by silica gel column chromatography, and drying until the mass is unchanged to obtain the corresponding product C 14 H 11 NO 2 (yield 93%), the reaction formula:
1 H NMR(400MHz,CDCl 3 )δ:8.19(d,J＝7.5Hz,2H),7.56(s,1H),7.45(d,J＝8.0hz, 1H), 7.14-7.02 (m, 4H), 3.87 (s, 3H). HRMS theoretical value C 14 H 11 NO 2 (M) + :225.0790, actual measured value: 225.0796.
example 4:
the nickel complex is used for catalyzing and synthesizing the aryl oxazole compound, and the specific process is as follows:
using the nickel complex prepared in example 1 as a catalyst, dissolving the nickel complex (0.001 mmol), benzoxazole (1.0 mmol), 4-methylchlorobenzene (1.1 mmol) and potassium phosphate (1.2 mmol) in 2mL of toluene, reacting at room temperature for 300 minutes, concentrating the reaction solution after the reaction is finished, separating by silica gel column chromatography directly, and drying until the mass is unchanged to obtain the corresponding product C 14 H 11 NO (92% yield), reaction formula:
1 H NMR(400MHz,CDCl 3 ) δ:8.22 (d, J =7.5hz, 2h), 7.50 (s, 1H), 7.42 (d, J =8.0hz, 1h), 7.18-7.08 (m, 4H), 2.53 (s, 3H). HRMS theoretical value C 14 H 11 NO(M) + :209.0841, actual measurements: 209.0840.
example 5:
the nickel complex is used for catalyzing and synthesizing the aryl oxazole compound, and the specific process is as follows:
using the nickel complex prepared in example 1 as a catalyst, dissolving nickel complex (0.001 mmol), benzoxazole (1.0 mmol), 4-cyanobenzene (1.1 mmol) and potassium carbonate (1.2 mmol) in 2mL of toluene, reacting at room temperature for 180 minutes, concentrating the reaction solution after the reaction is finished, separating the reaction solution by silica gel column chromatography directly, and drying until the mass is unchanged to obtain the corresponding product C 14 H 8 N 2 O (93% yield), reaction formula:
1 H NMR(400MHz,CDCl 3 )δ:8.28(d,J＝7.0Hz,2H),7.55(s,1H),7.43(d,J＝8.0Hz,1H),7.227.12 (m, 4H). HRMS theoretical value C 14 H 8 N 2 O(M) + :220.0637, actual measurement: 220.0642.
example 6:
the nickel complex is used for catalyzing and synthesizing the aryl oxazole compound, and the specific process is as follows:
using the nickel complex prepared in example 1 as a catalyst, dissolving the nickel complex (0.001 mmol), benzoxazole (1.0 mmol), 2-methylchlorobenzene (1.1 mmol) and potassium phosphate (1.2 mmol) in toluene 2mL, reacting at room temperature for 220 minutes, concentrating the reaction solution after completion, separating by silica gel column chromatography, and drying until the mass is unchanged to obtain the corresponding product C 14 H 11 NO (90% yield), the reaction:
1 H NMR(400MHz,CDCl 3 ) δ:8.26 (d, J =7.0hz, 2h), 7.55 (s, 1H), 7.49 (d, J =7.0hz, 1h), 7.06-6.99 (m, 4H), 2.55 (s, 3H). HRMS theoretical value C 14 H 11 NO(M) + :209.0841, actual measurements: 209.0846.
example 7:
the nickel complex is used for catalyzing and synthesizing the aryl oxazole compound, and the specific process is as follows:
taking the nickel complex prepared in example 1 as a catalyst, dissolving the nickel complex (0.001 mmol), benzoxazole (1.0 mmol), 3-chloropyridine (1.1 mmol) and potassium carbonate (1.2 mmol) in 2mL of toluene, reacting at room temperature for 240 minutes, directly separating the concentrated reaction solution by silica gel column chromatography, and drying until the mass is unchanged to obtain the corresponding product C 12 H 8 N 2 O (92% yield), the reaction formula:
1 H NMR(400MHz,CDCl 3 )δ:9.47(s,1H),8.76(d,J＝5.0Hz,1H),8.50(d,J＝8.0Hz,1H),7.58(s,1H),7.49-7.45(m,2H),721 (d, J =8.0hz, 1h), 2.50 (s, 3H). HRMS theoretical value C 12 H 8 N 2 O(M) + :196.0637, actual measurement: 196.0642.
the embodiments described above are described to facilitate an understanding and use of the invention by those skilled in the art. It will be readily apparent to those skilled in the art that various modifications to these embodiments may be made, and the generic principles described herein may be applied to other embodiments without the use of the inventive faculty. Therefore, the present invention is not limited to the above embodiments, and those skilled in the art should make improvements and modifications within the scope of the present invention based on the disclosure of the present invention.
Claims (9)
1. A method for synthesizing an aryl oxazole compound by using a nickel complex catalyst is characterized by comprising the following steps: taking a nickel complex containing an ortho-position carborane alkyl benzothiazole structure as a catalyst, taking benzoxazole and halogenated aromatic compounds as raw materials, and carrying out an oxidative coupling reaction at room temperature in the presence of alkali to obtain an aryloxazole compound; the structural formula of the nickel complex containing the ortho-carborane-based benzothiazole structure is shown as follows:
wherein ". -" is a boron hydrogen bond;
the halogenated aromatic hydrocarbon compound is one of chlorobenzene, 4-methoxy chlorobenzene, 4-methyl chlorobenzene, 4-cyano chlorobenzene, 2-methyl chlorobenzene and 3-chloropyridine.
2. The method for catalytically synthesizing the aryl oxazole compound by using the nickel complex as claimed in claim 1, which comprises the following steps: dissolving a nickel complex containing an ortho-position carborane-based benzothiazole structure, benzoxazole, a halogenated aromatic compound and alkali in an organic solvent, reacting at room temperature for 100-300min, and separating and purifying to obtain the aryl oxazole compound.
3. The method for catalytically synthesizing the aryl oxazole compound by using the nickel complex as claimed in claim 2, wherein the base is potassium carbonate or potassium phosphate.
4. The method for catalytically synthesizing the aryl oxazole compound by using the nickel complex as claimed in claim 2, wherein the organic solvent is toluene.
5. The method for catalytically synthesizing the aryl oxazole compound by using the nickel complex as claimed in claim 2, wherein the molar ratio of the nickel complex containing the ortho-position carborane-based benzothiazole structure, the benzoxazole, the halogenated aromatic compound and the base is (0.001-0.002): 1.1.
6. The method for synthesizing the aryl oxazole compound by using the nickel complex as the catalyst according to claim 1, wherein the method for preparing the nickel complex containing the ortho-carborane-based benzothiazole structure comprises the following steps:
1) At-80 deg.C to-75 deg.CnAdding a BuLi solution into an ortho-carborane solution, stirring, and reacting at room temperature for 30-60min;
2) Adding bromobenzothiazole, and reacting at room temperature for 6-8h;
3) Adding NiCl 2 Reacting at room temperature for 3-5h, and carrying out post-treatment to obtain the nickel complex.
7. The method for synthesizing the aryl oxazole compound by using the nickel complex as the catalyst according to claim 6, wherein in the step 1), the aryl oxazole compound is synthesized by using the nickel complex as the catalystn-The BuLi solution isn-The solution of BuLi in n-hexane is a tetrahydrofuran solution of ortho-carborane.
8. The method for synthesizing the aryl oxazole compound by using the nickel complex as the catalyst according to claim 6, wherein in the step 3), the post-treatment process comprises the following steps: standing and filtering after the reaction is finished, decompressing and pumping out the solvent to obtain a crude product, and then carrying out column chromatography separation on the crude product; in the process of column chromatography separation, an eluent is a mixed solvent of petroleum ether and tetrahydrofuran, and the volume ratio of the petroleum ether to the tetrahydrofuran is (5-10): 1.
9. The method for synthesizing the aryl oxazole compound by using the nickel complex as the catalyst according to claim 6, wherein the method is characterized in thatn-BuLi, ortho-carborane, bromobenzothiazole, niCl 2 The molar ratio of (2.2-3.0) to (1), (0.8-1.2) to (0.8-1.2).
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