CN109457268A - A kind of method of electro-catalysis benzamide compound synthesis benzoxazoles - Google Patents
A kind of method of electro-catalysis benzamide compound synthesis benzoxazoles Download PDFInfo
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Abstract
A kind of method that the present invention discloses electro-catalysis benzamide compound synthesis benzoxazoles, in tetrabutyl ammonium hexafluorophosphate (TBAPF6) be passed through constant current in aqueous solution and make benzamide compound cyclization generates the reaction of benzoxazoles under alkaline condition, invent a kind of environmental-friendly, easy to operate, safety is cheap, efficiently prepares the method for benzoxazoles.Compared with prior art, the method is not only able to be applicable in a large amount of functional group, and yield is high, and by-product is few, and easy to operate, safety, low in cost, environmental protection；
Description
Technical field
The invention belongs to the electro-catalysis benzamide compound of constant current synthesis benzoxazoles is passed through in a kind of water
Method.
Background technique
Benzoxazoles is a kind of double bond containing nitrogen oxygen five member ring heterocyclic compound, is had extensively in fields such as medicine, material, pesticides
General application.The synthetic method of benzoxazoles is mainly raw material and carboxylic acid or acyl chlorides in metal catalytic using o-aminophenol at present
Agent or high molecular material support the lower method for carrying out cyclization, also there is a method for carrying out self-condensation using benzamide, but this
A method is longer commonly using the metallic catalyst of some Nano grades or reaction time.Summary, which is got, sees that synthesis benzo is disliked at present
Time-consuming for the method for azoles, and using material complexity, economic benefit is low.
Electrochemistry auxiliary synthetic method refers under constant current conditions, directly gives reactant energy, promotes reaction faster
Energy barrier is more easily crossed over, makes to react the synthetic method faster carried out, utilizes electrochemistry auxiliary synthetic method preparation
Sample often has the potentiality of mass production, is the powerful for being synthesized to industrialization large-scale production on a small quantity from laboratory.
In recent years, sustainability, low power consuming, low pollution Green Chemistry conceptually propose so that water this be easy to get, be honest and clean
Valence, be easy to get, nonflammable and nontoxic solvent has obtained widely paying close attention to.Serving as reaction medium using water can be improved instead
It answers rate and is easily isolated product, can simplify laboratory operating procedures, save the cost meets the theory of sustainable development.
Summary of the invention
The object of the present invention is to provide a kind of methods of electro-catalysis benzamide compound synthesis benzoxazoles.
The object of the present invention is achieved like this, The technical solution adopted by the invention is as follows:
The purpose is that substituted benzamide and alkali are added in flask in tetrabutyl ammonium hexafluorophosphate (TBAPF6) in aqueous solution
It is passed through constant current to be reacted, reaction equation is as follows:
According to the present invention, substrate (I) is substituted benzamide, can synthesize benzoxazoles class compound in this reaction system.
Wherein R1For 3 or 4 on benzamide substitutions, can for hydrogen atom, halogen atom, hydroxyl, methyl, ethyl,
Propyl, butyl, isopropyl, methoxyl group, acetyl group, nitro or cyano；
Products therefrom (II) according to the present invention, wherein R1It is on benzamide 3,4 substitutions can be former for hydrogen atom, halogen
Son, hydroxyl, methyl, ethyl, propyl, butyl, isopropyl, methoxyl group, acetyl group, nitro or cyano.Wherein R2For amino, first
Base, ethyl, propyl, butyl, methylamino, ethylamino, the third amino, fourth amino, phenyl, benzyl, phenethyl, phenylpropyl, benzene fourth
Base, benzene hydroxyl, Phenoxymethyl, phenylacetyl group, benzene nitro, benzene cyano, halogen phenyl, pyridine, piperazine, thiazole or acetyl group.
Electrode can be used C-C electrode, Pt-Pt electrode, Pt-Ag electrode or Pt-C in above-mentioned specific steps
Electrode, preferably Pt-Pt electrode.
Alkali used in above-mentioned specific steps can be potassium hydroxide, sodium hydroxide or cesium carbonate, preferably cesium carbonate.
TBAPF in above-mentioned specific steps6Concentration of aqueous solution is 10-20 mmol/L, preferably 10 mmol/L.
The usage amount of alkali is the 10-30% of the molal weight of reaction substrate substituted benzamide in above-mentioned specific steps,
Preferably 20%.
The constant current being passed through in above-mentioned specific steps is 10-30 mA, preferably 20 mA.
The reaction time is 5-30 min, preferably 10 min in above-mentioned specific steps.
The volume of reaction dissolvent will affect conductivity in above-mentioned specific steps, and every mol reaction substrate substituted benzamide adds
Enter the TBAPF of 1-3 ml6Aqueous solution, preferably 2 ml.
Advantages of the present invention are as follows: the present invention, which provides, to be passed through constant current in a kind of water and synthesized using benzamide compound
The method of benzoxazoles, benzamide compound and alkali are in TBAPF6Constant current is passed through in aqueous solution to be reacted.This hair
Bright is that one kind is environmental-friendly, and easy to operate, safety is cheap, efficiently prepares the method for benzoxazoles class compound.With existing skill
Art is compared, and the method is not only able to be applicable in a large amount of functional group, and yield is high, and by-product is few, and easy to operate, safety, cost
It is cheap, environmental protection.
Specific embodiment
The following examples will be further described the present invention, but not thereby limiting the invention.
Embodiment 1: the TBAPF of 1 mmol of benzamide, 10 mmol/L benzoxazoles: are added in flask6Aqueous solution 2
Ml, 0.2 mmol of cesium carbonate react 10 min under Pt-Pt electrode under 20 mA constant currents, ethyl acetate extraction is depressurized dense
Contracting, product silica gel post separation obtain white solid, yield 99%.
Embodiment 2:2-methylbenzoxazole: the preparation method is the same as that of Example 1, and electrode replaces Pt using Pt-Ag electrode
- Pt electrode, addition areNMethyl benzamide obtains white solid, yield 94%.
Embodiment 3:2-ethyl benzoxazoles: the preparation method is the same as that of Example 1, and electrode replaces Pt-using C-C electrode
Pt electrode, addition areNEthyl benzamide obtains white solid, yield 94%.
Embodiment 4:2-propyl benzoxazoles: the preparation method is the same as that of Example 1, and electrode replaces Pt-using Pt-C electrode
Pt electrode, addition areNPropyl benzamide obtains white solid, yield 95%.
Embodiment 5:2-butyl benzoxazoles: the preparation method is the same as that of Example 1, and addition isNButyl benzamide,
Obtain white solid, yield 96%.
Embodiment 6:2-amino benzoxazoles: the preparation method is the same as that of Example 1, and addition is benzoyl hydrazine, obtains white solid
Body, yield 97%.
Embodiment 7:2-methylamino benzoxazoles: the preparation method is the same as that of Example 1, and addition isN(amino methyl) benzene
Formamide obtains white-yellowish solid, yield 96%.
Embodiment 8:2-ethylamino benzoxazoles: the preparation method is the same as that of Example 1, and addition isN(amino-ethyl) benzene
Formamide obtains white-yellowish solid, yield 97%.
Embodiment 9:2-the third amino benzoxazoles: the preparation method is the same as that of Example 1, and addition is N-(aminopropyl) benzene
Formamide obtains white-yellowish solid, yield 94%.
Embodiment 10:2-fourth amino benzoxazoles: the preparation method is the same as that of Example 1, and addition isN(aminobutyl)
Benzamide obtains white-yellowish solid, yield 95%.
Embodiment 11:2-phenyl benzoxazoles: the preparation method is the same as that of Example 1, and addition is N-phenylbenzamaide,
Obtain white solid, yield 96%.
Embodiment 12:2- p - Benzyl benzoxazoles: the preparation method is the same as that of Example 1, and addition isN –pToluene
Yl-benzamide obtains white solid, yield 96%.
Embodiment 13:2- o - Benzyl benzoxazoles: the preparation method is the same as that of Example 1, and addition isN –oToluene
Yl-benzamide obtains white solid, yield 95%.
Embodiment 14:2- m - Benzyl benzoxazoles: the preparation method is the same as that of Example 1, and addition isN –mToluene
Yl-benzamide obtains white solid, yield 97%.
Embodiment 15:2- p - Phenethyl benzoxazoles: the preparation method is the same as that of Example 1, and addition isN(4-second
Base phenyl) benzamide, obtain white solid, yield 96%.
Embodiment 16:2- o - Phenethyl benzoxazoles: the preparation method is the same as that of Example 1, and addition isN(2-second
Base phenyl) benzamide, obtain white solid, yield 94%.
Embodiment 17:2- m - Phenethyl benzoxazoles: the preparation method is the same as that of Example 1, and addition isN(3-second
Base phenyl) benzamide, obtain white solid, yield 92%.
Embodiment 18:2- o - Phenylpropyl benzoxazoles: the preparation method is the same as that of Example 1, and addition isN(2-the third
Base phenyl) benzamide, obtain white solid, yield 94%.
Embodiment 19:2- m - Phenylpropyl benzoxazoles: the preparation method is the same as that of Example 1, and addition isN(3-the third
Base phenyl) benzamide, obtain white solid, yield 96%.
Embodiment 20:2- p - Phenylpropyl benzoxazoles: the preparation method is the same as that of Example 1, and addition isN(4-the third
Base phenyl) benzamide, obtain white solid, yield 97%.
Embodiment 21:2- o - Benzene butyl benzoxazoles: the preparation method is the same as that of Example 1, and addition isN(2-fourths
Base phenyl) benzamide, obtain white solid, yield 98%.
Embodiment 22:2- m - Benzene butyl benzoxazoles: the preparation method is the same as that of Example 1, and addition isN(3-fourths
Base phenyl) benzamide, obtain white solid, yield 96%.
Embodiment 23:2- p - Benzene butyl benzoxazoles: the preparation method is the same as that of Example 1, and addition isN(4-fourths
Base phenyl) benzamide, obtain white solid, yield 94%.
Embodiment 24:2-(2-methoxyphenyl) benzoxazoles: the preparation method is the same as that of Example 1, and addition isN –
(2-methoxyphenyl) benzamide, obtains white solid, yield 96%.
Embodiment 25:2-(3-methoxyphenyl) benzoxazoles: the preparation method is the same as that of Example 1, and addition isN –
(3-methoxyphenyl) benzamide, obtains white solid, yield 94%.
Embodiment 26:2-(4-methoxyphenyl) benzoxazoles: the preparation method is the same as that of Example 1, and addition isN –
(4-methoxyphenyl) benzamide, obtains white solid, yield 94%.
Embodiment 27:2-(2-acetylphenyl) benzoxazoles: the preparation method is the same as that of Example 1, and addition isN(2
Acetylphenyl) benzamide, obtain white solid, yield 94%.
Embodiment 28:2-(3-acetylphenyl) benzoxazoles: the preparation method is the same as that of Example 1, and addition isN(3
Acetylphenyl) benzamide, obtain white solid, yield 94%.
Embodiment 29:2-(4-acetylphenyl) benzoxazoles: the preparation method is the same as that of Example 1, and addition isN(4
Acetylphenyl) benzamide, obtain yellow solid, yield 93%.
Embodiment 30:2-(2-nitrobenzophenone) benzoxazoles: the preparation method is the same as that of Example 1, and addition isN(2-
Nitrobenzophenone) benzamide, obtain yellow solid, yield 96%.
Embodiment 31:2-(3-nitrobenzophenone) benzoxazoles: the preparation method is the same as that of Example 1, and addition isN(3-
Nitrobenzophenone) benzamide, obtain yellow solid, yield 97%.
Embodiment 32:2-(4-nitrobenzophenone) benzoxazoles: the preparation method is the same as that of Example 1, and addition isN(4-
Nitrobenzophenone) benzamide, obtain yellow solid, yield 94%.
Embodiment 33:2-(2-cyano-phenyl) benzoxazoles: the preparation method is the same as that of Example 1, and addition isN(2-
Cyano-phenyl) benzamide, obtain faint yellow solid, yield 96%.
Embodiment 34:2-(3-cyano-phenyl) benzoxazoles: the preparation method is the same as that of Example 1, and addition isN(3-
Cyano-phenyl) benzamide, obtain faint yellow solid, yield 94%.
Embodiment 35:2-(4-cyano-phenyl) benzoxazoles: the preparation method is the same as that of Example 1, and addition isN(4-
Cyano-phenyl) benzamide, obtain faint yellow solid, yield 96%.
Embodiment 36:2-(2-hydroxy phenyl) benzoxazoles: the preparation method is the same as that of Example 1, and addition isN(2-
Hydroxy phenyl) benzamide, obtain yellow solid, yield 96%.
Embodiment 37:2-(3-hydroxy phenyl) benzoxazoles: the preparation method is the same as that of Example 1, and addition isN(3-
Hydroxy phenyl) benzamide, obtain yellow solid, yield 95%.
Embodiment 38:2-(4-hydroxy phenyl) benzoxazoles: the preparation method is the same as that of Example 1, and addition isN(4-
Hydroxy phenyl) benzamide, obtain yellow solid, yield 94%.
Embodiment 39:2-(4-fluorophenyl) benzoxazoles: the preparation method is the same as that of Example 1, and addition isN(4-fluorine
Phenyl) benzamide, obtain white solid, yield 93%.
Embodiment 40:2-(3-fluorophenyl) benzoxazoles: the preparation method is the same as that of Example 1, and addition isN(3-fluorine
Phenyl) benzamide, obtain white solid, yield 92%.
Embodiment 41:2-(2-fluorophenyl) benzoxazoles: the preparation method is the same as that of Example 1, and addition isN(2-fluorine
Phenyl) benzamide, obtain white solid, yield 92%.
Embodiment 42:2-(4-chlorphenyl) benzoxazoles: the preparation method is the same as that of Example 1, and addition isN(4-chlorine
Phenyl) benzamide, obtain white solid, yield 93%.
Embodiment 43:2-(3-chlorphenyl) benzoxazoles: the preparation method is the same as that of Example 1, and addition isN(3-chlorine
Phenyl) benzamide, obtain white solid, yield 93%.
Embodiment 44:2-(2-chlorphenyl) benzoxazoles: the preparation method is the same as that of Example 1, and addition isN(2-chlorine
Phenyl) benzamide, obtain white solid, yield 92%.
Embodiment 45:2-(4-bromophenyl) benzoxazoles: the preparation method is the same as that of Example 1, and addition isN(4-bromines
Phenyl) benzamide, obtain white solid, yield 95%.
Embodiment 46:2-(3-bromophenyl) benzoxazoles: the preparation method is the same as that of Example 1, and addition isN(3-bromines
Phenyl) benzamide, obtain white solid, yield 90%.
Embodiment 47:2-(2-bromophenyl) benzoxazoles: the preparation method is the same as that of Example 1, and addition isN(2-bromines
Phenyl) benzamide, obtain white solid, yield 92%.
Embodiment 48:2-pyridyl group benzoxazoles: the preparation method is the same as that of Example 1, and addition isNPyridyl group benzoyl
Amine obtains yellow solid, yield 95%.
Embodiment 49:2-thiazolyl benzoxazoles: the preparation method is the same as that of Example 1, and addition isNThiazolyl benzoyl
Amine obtains yellow solid, yield 94%.
Embodiment 50:2-piperazinyl benzoxazoles: the preparation method is the same as that of Example 1, and addition isNPiperazinyl phenyl formyl
Amine obtains white liquid, yield 96%.
Embodiment 51:2-acetyl group benzoxazoles: the preparation method is the same as that of Example 1, and addition isNAcetylbenzene formyl
Amine obtains faint yellow solid, yield 94%.
Embodiment 52:7-hydroxy benzo oxazole: the preparation method is the same as that of Example 1, and addition is 2-hydroxybenzamides,
Obtain white liquid, yield 94%.
Embodiment 53:6-hydroxybenzamide: the preparation method is the same as that of Example 1, and addition is 3-hydroxybenzamides,
Obtain white solid, yield 97%.
Embodiment 54:5-hydroxybenzamide: the preparation method is the same as that of Example 1, and addition is 4-hydroxybenzamides,
Obtain white solid, yield 96%.
Embodiment 55:7-fluorine benzoxazoles: the preparation method is the same as that of Example 1, and addition is 2-fluorobenzamides, obtains white
Color liquid, yield 95%.
Embodiment 56:6-fluorine benzoxazoles: the preparation method is the same as that of Example 1, and addition is 3-fluorobenzamides, obtains white
Color solid, yield 96%.
Embodiment 57:5-fluorine benzoxazoles: the preparation method is the same as that of Example 1, and addition is 4-fluorobenzamides, obtains white
Color solid, yield 95%.
Embodiment 58:7-chlorobenzene diozaiole: the preparation method is the same as that of Example 1, and addition is 2-chlorobenzamides, obtains white
Color liquid, yield 94%.
Embodiment 59:6-chlorobenzene diozaiole: the preparation method is the same as that of Example 1, and addition is 3-chlorobenzamides, obtains white
Color solid, yield 95%.
Embodiment 60:5-chlorobenzene diozaiole: the preparation method is the same as that of Example 1, and addition is 4-chlorobenzamides, obtains white
Color solid, yield 93%.
Embodiment 61:7-bromine benzoxazoles: the preparation method is the same as that of Example 1, and addition is 2-brombenzamides, obtains white
Color liquid, yield 94%.
Embodiment 62:6-bromine benzoxazoles: the preparation method is the same as that of Example 1, and addition is 3-brombenzamides, obtains white
Color solid, yield 93%.
Embodiment 63:5-bromine benzoxazoles: the preparation method is the same as that of Example 1, and addition is 4-brombenzamides, obtains white
Color solid, yield 97%.
Embodiment 64:7-methylbenzoxazole: the preparation method is the same as that of Example 1, and addition is 2-methyl benzamides,
Obtain white liquid, yield 95%.
Embodiment 65:6-methylbenzoxazole: the preparation method is the same as that of Example 1, and addition is 3-methyl benzamides,
Obtain white solid, yield 96%.
Embodiment 66:5-methylbenzoxazole: the preparation method is the same as that of Example 1, and addition is 4-methyl benzamides,
Obtain white solid, yield 96%.
Embodiment 67:7-ethyl benzoxazoles: the preparation method is the same as that of Example 1, and addition is 2-ethyl benzamides,
Obtain white liquid, yield 96%.
Embodiment 68:6-ethyl benzoxazoles: the preparation method is the same as that of Example 1, and addition is 3-ethyl benzamides,
Obtain white solid, yield 94%.
Embodiment 69:5-ethyl benzoxazoles: the preparation method is the same as that of Example 1, and addition is 4-ethyl benzamides,
Obtain white solid, yield 95%.
Embodiment 70:7-propyl benzoxazoles: the preparation method is the same as that of Example 1, and addition is 2-propyl benzamides,
Obtain white liquid, yield 92%.
Embodiment 71:6-propyl benzoxazoles: the preparation method is the same as that of Example 1, and addition is 3-propyl benzamides,
Obtain white solid, yield 92%.
Embodiment 72:5-propyl benzoxazoles: the preparation method is the same as that of Example 1, and addition is 4-propyl benzamides,
Obtain white solid, yield 93%.
Embodiment 73:7-butyl benzoxazoles: the preparation method is the same as that of Example 1, and addition is 2-butyl benzamides,
Obtain white liquid, yield 96%.
Embodiment 74:6-butyl benzoxazoles: the preparation method is the same as that of Example 1, and addition is 3-butyl benzamides,
Obtain white solid, yield 91%.
Embodiment 75:5-butyl benzoxazoles: the preparation method is the same as that of Example 1, and addition is 4-butyl benzamides,
Obtain white solid, yield 93%.
Embodiment 76:7-isopropyl benzoxazoles: the preparation method is the same as that of Example 1, and addition is 2-cumene first
Amide obtains white liquid, yield 92%.
Embodiment 77:6-isopropyl benzoxazoles: the preparation method is the same as that of Example 1, and addition is 3-cumene first
Amide obtains white solid, yield 90%.
Embodiment 78:5-isopropyl benzoxazoles: the preparation method is the same as that of Example 1, and addition is 4-cumene first
Amide obtains white solid, yield 91%.
Embodiment 79:7-methoxyl group benzoxazoles: the preparation method is the same as that of Example 1, and addition is 2-methoxybenzene first
Amide obtains white liquid, yield 90%.
Embodiment 80:6-methoxyl group benzoxazoles: the preparation method is the same as that of Example 1, and addition is 3-methoxybenzene first
Amide obtains white solid, yield 89%.
Embodiment 81:5-methoxyl group benzoxazoles: the preparation method is the same as that of Example 1, and addition is 4-methoxybenzene first
Amide obtains white solid, yield 91%.
Claims (8)
1. a kind of method of electro-catalysis benzamide compound synthesis benzoxazoles, such as chemical equation (A), specific steps
It is as follows: substituted benzamide, alkali and tetrabutyl ammonium hexafluorophosphate (TBAPF being added in flask6) aqueous solution, it then passes to constant
Electric current is reacted, and ethyl acetate extraction is concentrated under reduced pressure, uses silica gel post separation product；
(A)
Wherein R1For 3 on benzamide, substitution on 4 is hydrogen atom, halogen atom, hydroxyl, methyl, ethyl, propyl, fourth
Base, isopropyl, methoxyl group, acetyl group, nitro or cyano；R2For amino, methyl, ethyl, propyl, butyl, methylamino, second ammonia
Base, the third amino, fourth amino, phenyl, benzyl, phenethyl, phenylpropyl, benzene butyl, benzene hydroxyl, Phenoxymethyl, phenylacetyl group, benzene
Nitro, benzene cyano, halogen phenyl, pyridine, piperazine, thiazole or acetyl group.
2. the method as described in claim 1, it is characterised in that it is C-C that this, which is passed through the reaction electrode that constant current is reacted,
Electrode, Pt-Pt electrode, Pt-Ag electrode or Pt-C electrode, preferably Pt-Pt electrode.
3. the method as described in claim 1, it is characterised in that the alkali that the reaction uses is potassium hydroxide, sodium hydroxide or carbonic acid
Caesium, preferably cesium carbonate.
4. the method as described in claim 1, it is characterised in that TBAPF in specific steps6Concentration of aqueous solution is 10-20
Mmol/L, preferably 10 mmol/L.
5. the method as described in claim 1, it is characterised in that the usage amount of alkali is reaction substrate substituted benzoyl in specific steps
The 10-30% of the molal weight of amide, preferably 20%.
6. the method as described in claim 1, it is characterised in that the constant current being passed through in specific steps is 10-30 mA, excellent
Select 20 mA.
7. the method as described in claim 1, it is characterised in that the time reacted in specific steps be 5-30 min, preferably 10
min。
8. method as described in claim 1 or 4, it is characterised in that the volume of reaction dissolvent will affect conduction in specific steps
The TBAPF of 1-3 ml is added in rate, every mol reaction substrate substituted benzamide6Aqueous solution, preferably 2 ml.
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| CN113818033A (en) * | 2021-10-14 | 2021-12-21 | 诚达药业股份有限公司 | Electrochemical synthesis method of 2-substituted benzoxazole derivative |
| CN114990592A (en) * | 2022-05-27 | 2022-09-02 | 中国农业大学 | Method for synthesizing multi-substituted oxazole through electrocatalysis |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110184621A (en) * | 2019-06-28 | 2019-08-30 | 福建医科大学 | A method of using bromide as bromating agent, the electro-catalysis in water phase prepares more bromophenol compounds |
| CN110528020A (en) * | 2019-09-19 | 2019-12-03 | 青岛科技大学 | The preparation method of isoxazole and isoquinolinone derivatives under a kind of electro-catalysis |
| CN110528020B (en) * | 2019-09-19 | 2021-05-14 | 青岛科技大学 | Preparation method of isoxazolo isoquinolinone derivative under electrocatalysis |
| CN113818033A (en) * | 2021-10-14 | 2021-12-21 | 诚达药业股份有限公司 | Electrochemical synthesis method of 2-substituted benzoxazole derivative |
| CN113818033B (en) * | 2021-10-14 | 2022-10-14 | 诚达药业股份有限公司 | Electrochemical synthesis method of 2-substituted benzoxazole derivative |
| CN114990592A (en) * | 2022-05-27 | 2022-09-02 | 中国农业大学 | Method for synthesizing multi-substituted oxazole through electrocatalysis |
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