CN114990592A - Method for synthesizing multi-substituted oxazole through electrocatalysis - Google Patents
Method for synthesizing multi-substituted oxazole through electrocatalysis Download PDFInfo
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Abstract
The invention relates to electrochemical catalysis, and belongs to the field of organic synthesis. A method for synthesizing multi-substituted oxazole by electrocatalysis comprises the steps of adding acetonitrile into electrolyte, adding an aryl ethyl ketone derivative and an activator into an anode region, taking a carbon electrode as an anode and a platinum electrode as a cathode, and applying a voltage of 2.0-3.0V to start electrocatalytic oxidation to obtain an oxazole compound. In the reaction for synthesizing the oxazole by adopting the electrocatalysis, nitrogen atoms do not need to be introduced into the precursor molecules in advance in an amino or amide mode, the complexity of the design and the preparation of the precursor molecules is reduced, the range of electrocatalysis synthesis products of the oxazole is expanded, and the cost and the difficulty of the synthesis of the complex oxazole molecules are reduced. In the embodiment, a template reaction in electrocatalytic synthesis of 47 oxazoles is selected, and the universal yield is over 85%.
Description
Technical Field
The invention relates to electrochemical catalysis, in particular to a method for synthesizing polysubstituted oxazole through electrocatalysis.
Background
Heterocyclic compounds are very important compounds in organic chemistry, and oxazole compounds as five-membered oxygen-containing azole heterocyclic compounds with good biological activity are easy to form hydrogen bonds, coordinate with metal ions, generate hydrophobic effect, pi-pi accumulation, electrostatic effect and the like, so that various non-covalent bond interactions can be generated, certain special properties are shown, and the oxazole compounds have wide application potential and great development value in the fields of medicine, pesticide, chemistry, physics, material science and the like. As in agriculture, oxazoles are used to prepare various pesticides. At present, part of oxazole derivatives enter the market of pesticides and herbicides, for example, etoxazole (oxazoline derivatives) which is an insecticide can block the biosynthesis process of chitin in spiders. The oxazole compound has wide bioactivity, such as antifungal activity, antibacterial activity, anticancer activity, antiviral activity, antituberculosis activity, hypoglycemic activity, anticonvulsant activity, antiphlogistic and analgesic activity, etc. owing to the action of the oxazole compound with various enzymes and receptors in organisms, and is one of the important fields for research and development of new medicines. At present, more compounds containing oxazole rings are widely used in clinic as medicines, such as linezolid, and play an irreplaceable role in overcoming clinical drug resistance and treating infectious diseases. The oxazole compound is also a multifunctional intermediate for synthesizing natural products such as steroids, gibberellin and the like, has irreplaceable effects in many aspects, and can be applied to the fields of fluorescent whitening, luminescence, imaging and the like after being combined with other compounds. In addition, because the oxazole compound has a unique rigid structure, the substituent group of the oxazole compound can extend in a proper direction, and part of the oxazole compound shows the antitumor activity, the oxazole compound is widely applied to the pharmaceutical industry in modern medicine, and the oxazole compound has excellent results in the research of the antitumor field.
Many methods have been reported for synthesizing polysubstituted oxazoles, including (1) copper-catalyzed amidation of a vinyl halide ring; (2) catalytic cycloisomerization of propiolamide; (3) iodine/copper catalyzed serial oxidation cyclization reaction; (4) silver-mediated cycloaddition of isocyanides to acid chlorides, and the like. These are traditional transition metal catalyzed synthesis reactions with well established conditions, systematic systems, but some of these methods require toxic reagents, can produce byproducts that are difficult to control, and can cause environmental pollution, and also require exogenous oxidants, which increase process costs, even some of which are more harsh, require high temperatures and pressures, and add energy costs.
More importantly, in the precursor molecules for the electrocatalytic synthesis of oxazole in the prior art, nitrogen atoms must be introduced in advance in the form of amino or amide, which greatly limits the range of electrocatalytic synthesis products of oxazole.
Therefore, it is urgently needed to develop an effective method and strategy to realize the electrocatalytic oxazole synthesis process, so that the electrocatalytic oxazole synthesis process can be popularized to the field of organic synthesis by rectifying and reforming without the dilemma of introducing nitrogen-containing functional groups in advance.
Disclosure of Invention
The technical problem to be solved by the invention is to provide a method for synthesizing multi-substituted oxazole by electrocatalysis, and the synthesis of complex branches of the multi-substituted oxazole can be realized by a simple precursor compound on the premise of higher catalytic activity and catalytic selectivity.
Technical scheme
A method for synthesizing multi-substituted oxazole by electrocatalysis comprises the following steps of adding acetonitrile into electrolyte, adding aryl ethyl ketone derivative and activator into an anode region, taking a carbon electrode as an anode and a platinum electrode as a cathode, applying a voltage of 2.0-3.0V to start electrocatalytic oxidation, and obtaining an oxazole compound:
further, the structural formula of the arylethanone derivative comprises:
R 1 selected from phenyl, substituted by one or more R 0 Substituted phenyl, 2-naphthalene ring, 1-thiophene, 2-furan, 1-pyridine;
R 2 selected from hydrogen atoms, straight or branched chains, unsubstituted or substituted by 1 to 5 halogen atomsSubstituted C1-10 alkyl, substituted by zero or one or more R 0 Substituted phenyl, 2-naphthalene ring, 1-thiophene, 2-furan, 1-pyridine;
the R is 0 Selected from halogen, CN, nitro, C which is straight-chain or branched and is unsubstituted or substituted by 1 to 5 halogen atoms 1～10 Alkyl, straight or branched chain and unsubstituted or substituted by 1 to 5 halogen atoms 1～10 Alkoxy group of (2).
Further, R is 1 Selected from the group consisting of 0 Substituted phenyl, 2-naphthalene ring, 1-thiophene, 2-furan, 1-pyridine, R 2 Selected from the group consisting of 0 Substituted phenyl; the R is 0 Selected from halogen, CN, nitro, C which is straight-chain or branched and is unsubstituted or substituted by 1-5 halogen atoms 1～10 Alkyl, straight or branched chain and unsubstituted or substituted by 1 to 5 halogen atoms 1～10 Alkoxy group of (2).
Further, R is 1 Selected from the group consisting of 0 When it is a substituted phenyl radical, R 2 Selected from the group consisting of 0 Substituted phenyl, 2-naphthyl, 1-thiophene, 2-furan, 1-pyridine; the R is 0 Selected from halogen, CN, nitro, C which is straight-chain or branched and is unsubstituted or substituted by 1-5 halogen atoms 1～10 Alkyl, straight or branched chain and unsubstituted or substituted by 1 to 5 halogen atoms 1～10 Alkoxy group of (2).
Further, R is 1 Selected from C by one or more straight or branched chains 1～10 When the alkyl group of (1) is substituted with phenyl, R 2 Selected from a hydrogen atom or a methyl group.
Further, the voltage is preferably 2.3-2.7V, and more preferably 2.5V.
Further, the activator is selected from the group consisting of: acetic anhydride, pivalic anhydride, p-toluenesulfonic anhydride, trifluoroacetic anhydride, trifluoromethanesulfonic anhydride and methanesulfonic anhydride.
Further, the electrolyte is selected from one or more of tetrabutylammonium tetrafluoroborate, tetrabutylammonium hexafluorophosphate, lithium perchlorate, tetraethylammonium hexafluorophosphate and tetramethylammonium tetrafluoroborate.
Furthermore, the concentration of the diaryl ethyl ketone compound, the propiophenone compound and the acetophenone compound is 0.04-0.12M, the concentration of the activating agent is 0.1-0.5M, and the concentration of the electrolyte is 0.1-0.5M.
Further, the electrocatalysis reaction time is 8-25 h.
Advantageous effects
The method for the electrocatalysis of carboxylic acid cyanidation has the following beneficial effects:
1. in the reaction for synthesizing oxazole by adopting electrocatalysis, nitrogen atoms do not need to be introduced into the precursor molecules in advance in an amino or amide mode, so that the complexity of the design and preparation of the precursor molecules is greatly reduced, the range of electrocatalysis synthesis products of oxazole is expanded, and the cost and difficulty of the synthesis of complex oxazole molecules are reduced. In the embodiment, a template reaction in electrocatalytic synthesis of 47 oxazoles is selected, and the universal yield is over 85%.
2. No additional catalyst is needed, and the reaction is efficient enough;
3. the reaction environment is mild and simple, and harsh conditions such as high temperature and high pressure are not involved;
4. expensive reagents are not needed, and raw materials are not affected by the electrical steric hindrance of groups and are generally and easily obtained;
5. the reaction is suitable for synthesizing most of complex oxazole molecules and is easy for large-scale production.
Drawings
FIG. 1 is a diagram of a reaction apparatus according to the present invention;
FIG. 2 is a schematic view of an electrode according to the present invention;
FIG. 3 is a hydrogen spectrum (one) of a series of diphenylethanones of the present invention;
FIG. 4 is a carbon spectrum of a series of diphenylethanones of the present invention (II);
FIG. 5 is the hydrogen spectrum (III) of a series of diphenylethanones of the present invention;
FIG. 6 is a carbon spectrum (IV) of a series of diphenylethanones of the present invention;
FIG. 7 is a hydrogen spectrum (V) of a series of diphenylethanones of the present invention;
FIG. 8 is a carbon spectrum (VI) of a series of diphenylethanones of the present invention;
FIG. 9 is a hydrogen spectrum (VII) of propiophenone of the series of the present invention;
FIG. 10 is a carbon spectrum (eight) of a series of propiophenones of the present invention;
FIG. 11 is a hydrogen spectrum (nine) of acetophenone according to the present invention;
FIG. 12 is a carbon spectrum (ten) of acetophenone of the present invention series.
Detailed Description
The invention is described in detail below with reference to the accompanying drawings 1-12 and examples.
Example 1 electrocatalytic Synthesis of Diarylethanones
As shown in the reaction formula, the invention comprises a method for synthesizing the polysubstituted oxazole by using diaryl ethyl ketone compounds as raw materials. Adding 0.4mmol (positive electrode) of diarylethanone, 0.4M (positive electrode) of electrolyte and 10mL (negative electrode) of acetonitrile solvent into an electrolytic cell, fully stirring to obtain a colorless solution at the negative electrode region and a solution or suspension at the positive electrode region, adding 2.0mmol of activating agent into the positive electrode region, and continuously stirring to further dissolve the active agent into the solution at the positive electrode region. Carbon (+) | platinum (-) electrode material was mounted on the cell and a voltage of 2.50V was applied. After 8-25 h, the reaction is finished, the combined reaction solution of the immersed electrodes is subjected to desolventizing treatment, and the product of the polysubstituted oxazole is separated by column chromatography, is generally yellow oily liquid, and has the yield of more than 85%.
The method is suitable for diaryl ethyl ketone substituted by alkyl, alkoxy, halogen, cyano, nitro and the like, is also suitable for derivative diaryl ethyl ketone of naphthalene ring and heteroaromatic ring framework (furan, thiophene, pyridine and the like), and can also obtain a polysubstituted oxazole product in moderate to good yield.
By replacing the acetophenone derivatives of different substituents, the corresponding polysubstituted oxazole products are obtained in the following table (1):
by replacing the acetophenone derivatives of different substituents, the corresponding polysubstituted oxazole products yield is given in table (2) below:
EXAMPLE 2 electrocatalytic Synthesis of polysubstituted oxazoles from propiophenones
As shown in the reaction formula, the invention comprises a method for synthesizing the polysubstituted oxazole by using the propiophenone compound as a raw material. Adding 0.4mmol (positive pole) of the propiophenone compound, 0.4M (positive pole and negative pole) of electrolyte and 10mL (positive pole and negative pole) of solvent acetonitrile into an electrolytic cell, fully stirring to obtain a colorless solution at the negative pole region and a solution or suspension at the positive pole region, adding 2.0mmol of an activating agent into the positive pole region, continuously stirring, and further dissolving the positive pole region into a solution. Carbon (+) | platinum (-) electrode material was mounted on the cell and a voltage of 2.50V was applied. After 8-25 h, the reaction is finished, the combined reaction solution of the washed electrodes is subjected to desolventizing treatment, and the product of the substituted oxazole is separated by column chromatography, generally yellow oily liquid is obtained, and the yield is more than 85%.
The method is suitable for alkyl substituted phenyl ketone compounds, and can obtain a polysubstituted oxazole product with medium to good yield.
By replacing acetophenone derivatives of different substituents, the yields of the corresponding polysubstituted oxazole products are as in the following table (3):
EXAMPLE 3 electrocatalytic Synthesis of Polysubstituted oxazoles of acetophenone Compounds
As shown in the reaction formula, the invention comprises a method for synthesizing multi-substituted oxazole by taking acetophenone compounds as raw materials. Adding 0.4mmol (positive pole) of acetophenone compounds, 0.4M (positive and negative poles) of electrolytes and 10mL (positive and negative poles) of acetonitrile solvents into an electrolytic cell, fully stirring to obtain a colorless solution at the negative pole region and a solution or suspension at the positive pole region, adding 2.0mmol of an activating agent into the positive pole region, continuously stirring, and further dissolving the positive pole region into a solution. Carbon (+) | platinum (-) electrode material was mounted on the cell and a voltage of 2.50V was applied. After 8-25 h, the reaction is finished, the combined reaction solution of the washed electrodes is subjected to desolventizing treatment, and the product of the substituted oxazole is separated by column chromatography, generally yellow oily liquid is obtained, and the yield is more than 85%.
The method is suitable for alkyl substituted acetophenone compounds, and can obtain a polysubstituted oxazole product with moderate to good yield.
By replacing acetophenone derivatives of different substituents, the yields of the corresponding polysubstituted oxazole products are as in the following table (4):
discussion: it can be seen from the electrocatalytic synthesis of 47 polysubstituted oxazole products and corresponding yield data cumulatively provided by the above embodiment that the technical scheme adopts electrocatalytic synthesis of precursor molecules of oxazole without introducing nitrogen atoms in advance in an amino or amide manner, thereby greatly reducing the complexity of the precursor molecules, expanding the range of electrocatalytic synthesis products of oxazole, and reducing the cost and difficulty of the synthesis of complex oxazole molecules. And the general yield in the electrocatalytic synthesis of the 47 oxazoles is above 85%.
Claims (10)
1. A method for synthesizing multi-substituted oxazole by electrocatalysis is characterized by comprising the steps of adding acetonitrile into electrolyte, adding aryl ethyl ketone derivatives and activators in an anode region, using a carbon electrode as an anode and a platinum electrode as a cathode, and applying a voltage of 2.0-3.0V to start electrocatalysis oxidation to obtain an oxazole compound.
2. The method for electrocatalytic synthesis of polysubstituted oxazoles according to claim 1, wherein the arylethanone derivative structural formula comprises:
R 1 selected from phenyl, substituted by one or more R 0 Substituted phenyl, 2-naphthalene ring, 1-thiophene, 2-furan, 1-pyridine;
R 2 selected from hydrogen atoms, C which is linear or branched and unsubstituted or substituted by 1 to 5 halogen atoms 1～10 With zero or one or more R 0 Substituted phenyl, 2-naphthalene ring, 1-thiophene, 2-furan, 1-pyridine;
the R is 0 Selected from halogen, CN, nitro, C which is straight-chain or branched and is unsubstituted or substituted by 1-5 halogen atoms 1～10 Alkyl, straight or branched chain and unsubstituted or substituted by 1 to 5 halogen atoms 1～10 An alkoxy group of (2).
3. The process for the electrocatalytic synthesis of polysubstituted oxazoles of claim 2, wherein said R is 1 Selected from the group consisting of 0 Substituted phenyl, 2-naphthalene ring, 1-thiophene, 2-furan, 1-pyridine, R 2 Selected from the group consisting of 0 Substituted phenyl; said R is 0 Selected from halogen, CN, nitro, C which is straight-chain or branched and is unsubstituted or substituted by 1-5 halogen atoms 1～10 Alkyl, straight or branched chain and unsubstituted or substituted by 1 to 5 halogen atoms 1～10 Alkoxy group of (2).
4. Such as rightThe method for the electrocatalytic synthesis of polysubstituted oxazoles of claim 2, wherein R is 1 Selected from the group consisting of 0 When it is a substituted phenyl radical, R 2 Selected from the group consisting of 0 Substituted phenyl, 2-naphthalene ring, 1-thiophene, 2-furan, 1-pyridine; the R is 0 Selected from halogen, CN, nitro, C which is straight-chain or branched and is unsubstituted or substituted by 1-5 halogen atoms 1～10 Alkyl, straight or branched chain and unsubstituted or substituted by 1 to 5 halogen atoms 1～10 Alkoxy group of (2).
5. The process for the electrocatalytic synthesis of polysubstituted oxazoles of claim 2, wherein said R is 1 Selected from C by one or more straight or branched chains 1～10 When the alkyl group of (1) is substituted with phenyl, R 2 Selected from a hydrogen atom or a methyl group.
6. The process for the electrocatalytic synthesis of a polysubstituted oxazole according to any one of claims 1 to 5 wherein said voltage is between 2.3V and 2.7V.
7. The process for the electrocatalytic synthesis of polysubstituted oxazoles according to any one of claims 1 to 5, wherein said activator is selected from the group consisting of: acetic anhydride, pivalic anhydride, p-toluenesulfonic anhydride, trifluoroacetic anhydride, trifluoromethanesulfonic anhydride and methanesulfonic anhydride.
8. The method for electrocatalytic synthesis of a polysubstituted oxazole according to any one of the claims 1 to 5 wherein said electrolyte is selected from the group consisting of tetrabutylammonium tetrafluoroborate, tetrabutylammonium hexafluorophosphate, lithium perchlorate, tetraethylammonium hexafluorophosphate, tetramethylammonium tetrafluoroborate, alone or in combination.
9. The method for electrocatalytic synthesis of polysubstituted oxazole according to any one of claims 1 to 5 wherein the concentration of said diarylethanone compounds and propiophenone and acetophenone compounds is 0.04 to 0.12M, the concentration of the activator is 0.1 to 0.5M and the concentration of the electrolyte is 0.1 to 0.5M.
10. The method for electrocatalytic synthesis of polysubstituted oxazoles according to any one of claims 1 to 5, wherein the electrocatalytic reaction time is comprised between 8 and 25 hours.
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| 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 |
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