CN115074760B - Electrochemical synthesis method of 5-aminopyrazole-4-thiocyanate compound - Google Patents

Electrochemical synthesis method of 5-aminopyrazole-4-thiocyanate compound Download PDF

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CN115074760B
CN115074760B CN202210742555.8A CN202210742555A CN115074760B CN 115074760 B CN115074760 B CN 115074760B CN 202210742555 A CN202210742555 A CN 202210742555A CN 115074760 B CN115074760 B CN 115074760B
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aminopyrazole
thiocyanate
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CN115074760A (en
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钱朋
姜思琪
刘娇娇
汪文雁
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Fuyang Normal University
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Abstract

The invention discloses an electrochemical synthesis method of a 5-aminopyrazole-4-thiocyanate compound, which relates to the technical field of electrochemical synthesis and comprises the following steps: (1) electrocatalytic reaction: respectively adding thiocyanate, 5-aminopyrazole compounds, acid and solvent into a reaction tank, installing a catalytic electrode, and electrifying and stirring for reaction; (2) separation and purification: and (3) separating and purifying the solution after the electrocatalytic reaction is completed to obtain the 5-aminopyrazole-4-thiocyanate compound. According to the method, thiocyanate and 5-aminopyrazole compounds are used as reaction raw materials, and the 5-aminopyrazole-4-thiocyanate compounds are synthesized by a one-pot method under electrochemical conditions.

Description

Electrochemical synthesis method of 5-aminopyrazole-4-thiocyanate compound
Technical field:
the invention relates to the technical field of electrochemical synthesis, in particular to an electrochemical synthesis method of a 5-aminopyrazole-4-thiocyanate compound.
The background technology is as follows:
pyrazole is a five-membered heterocyclic compound containing two linked nitrogen atoms, a derivative of which is widely found in synthetic chemicals. Because of the high-efficiency broad-spectrum biological activity and wide application in the fields of medicines and agrochemicals, the compound has been widely paid attention to by workers in the related fields of organic chemistry, medicinal chemistry, biology and the like for many years, and especially the compound of N-aryl-5-aminopyrazole-4-thiocyanate with antifungal activity has the efficacy of resisting the trichophyton floccosum and trichophyton rubrum. The research shows that the inhibition effect of the molecule on the two fungi is no more than that of the clinical standard medicine ketoconazole. Thus, research on the synthetic methods thereof has been an important point of research by organic chemists. However, due to the presence of amino groups in the reaction substrate, it is difficult to be compatible in an oxidation system, and few studies are currently conducted on the synthesis of 5-aminopyrazole-4-thiocyanate compounds.
In 2020, the Choudhury group reported hydrogen peroxide-promoted C (sp 2) -H bond thiocyanate of N-aryl-5-aminopyrazole compounds, synthesizing a series of N-aryl-5-aminopyrazole-4-thiocyanate compounds (D.Ali, A.K.Panday, L.H.Choudhury.J.Org.Chem.2020,85,13610). Although this method can well achieve its synthesis, a large amount of hydrogen peroxide (8 equivalents) is required. The use of a large amount of chemical oxidizing agents can lead to complex reaction systems and low atomic economy, and can cause a large amount of waste liquid discharge in the industrial production process.
The invention comprises the following steps:
the invention aims to solve the technical problem of providing an electrochemical synthesis method of a 5-aminopyrazole-4-thiocyanate compound, which adopts a green electrochemical synthesis method to prepare the 5-aminopyrazole-4-thiocyanate compound in a reaction environment without adding metal and chemical oxidant so as to overcome the defects in the prior art.
The invention aims to provide an electrochemical synthesis method of a 5-aminopyrazole-4-thiocyanate compound, which comprises the following steps:
(1) Electrocatalytic reaction: respectively adding thiocyanate, 5-aminopyrazole compounds, acid and solvent into a reaction tank, installing a catalytic electrode, and electrifying and stirring for reaction;
(2) And (3) separating and purifying: and (3) separating and purifying the solution after the electrocatalytic reaction is completed to obtain the 5-aminopyrazole-4-thiocyanate compound.
The 5-aminopyrazole-4-thiocyanate compound has a structure shown as follows:
wherein R is 1 Is hydrogen、C 1 ～C 5 Alkyl, aryl; r is R 2 Is aryl or ester.
The beneficial effects of the invention are as follows: the invention provides an electrochemical synthesis method of a 5-aminopyrazole-4-thiocyanate compound, which adopts thiocyanate and 5-aminopyrazole compound as reaction raw materials, and synthesizes the 5-aminopyrazole-4-thiocyanate compound by a one-pot method under electrochemical conditions.
Description of the drawings:
FIG. 1 shows the product of example 1 of the present invention 1 H NMR；
FIG. 2 shows the product of example 1 of the present invention 13 C NMR；
FIG. 3 shows the product obtained in example 2 of the present invention 1 H NMR；
FIG. 4 shows the product obtained in example 2 of the present invention 13 C NMR；
FIG. 5 shows the product of example 3 of the present invention 1 H NMR；
FIG. 6 shows the product of example 3 of the present invention 13 C NMR；
FIG. 7 shows the product obtained in example 4 of the present invention 1 H NMR；
FIG. 8 shows the product obtained in example 4 of the present invention 13 C NMR；
FIG. 9 shows the product obtained in example 5 of the present invention 1 H NMR；
FIG. 10 shows the product obtained in example 5 of the present invention 13 C NMR；
FIG. 11 shows the product of example 6 of the present invention 1 H NMR；
FIG. 12 shows the product of example 6 of the present invention 13 C NMR。
The specific embodiment is as follows:
the invention is further described below with reference to specific embodiments and illustrations in order to make the technical means, the creation features, the achievement of the purpose and the effect of the implementation of the invention easy to understand.
The invention provides an electrochemical synthesis method of a 5-aminopyrazole-4-thiocyanate compound, which comprises the following steps:
(1) Electrocatalytic reaction: respectively adding thiocyanate, 5-aminopyrazole compounds, acid and solvent into a reaction tank, installing a catalytic electrode, and electrifying and stirring for reaction;
(2) And (3) separating and purifying: and (3) separating and purifying the solution after the electrocatalytic reaction is completed to obtain the 5-aminopyrazole-4-thiocyanate compound.
The 5-aminopyrazole-4-thiocyanate compound has a structure shown as follows:
wherein R is 1 Is hydrogen, C 1 ～C 5 Alkyl, aryl; r is R 2 Is aryl or ester.
Preferably, the thiocyanate is one of potassium thiocyanate, ammonium thiocyanate and sodium thiocyanate.
Preferably, the 5-aminopyrazole compound has a structure as shown below:
wherein R is 1 Is hydrogen, C 1 ～C 5 Alkyl, aryl; r is R 2 Is aryl or ester.
Preferably, the mass ratio of the 5-aminopyrazole compound to the thiocyanate is 1:1-1:4.
Preferably, the initial concentration of the 5-aminopyrazole compound is 0.05-0.2 mol/L.
Preferably, the acid is one of acetic acid (acetic acid), benzoic acid, hydrochloric acid, sulfuric acid and diphenyl phosphoric acid, and the amount of the substance is 30-120% of that of the 5-aminopyrazole compound.
Preferably, the temperature of the stirring reaction is 0 to 80 ℃.
Preferably, the solvent is one or more of dimethyl sulfoxide, N-dimethylformamide, methanol, ethanol, N-methylpyrrolidone, N-dimethylacetamide, acetonitrile, water and 1, 2-dichloroethane.
Preferably, the electrode is a conventional commercially available electrode material such as a platinum electrode, a carbon electrode, a nickel electrode, a copper electrode, or the like.
Preferably, the separation and purification method is one of column chromatography, liquid chromatography, distillation and recrystallization. Further preferably, the separation and purification method is column chromatography. The solution after completion of the reaction was dried under reduced pressure, and the residue was separated by silica gel column chromatography.
The eluent of the column chromatography is petroleum ether/ethyl acetate, which is not to say that other eluent systems cannot be used, so long as the reagent meeting the eluting purpose can be used.
The chemical reaction formula of the 5-aminopyrazole-4-thiocyanate compound is as follows:
the invention realizes the reaction of the 5-aminopyrazole compound and thiocyanate under the electrochemical condition for the first time, and the 5-aminopyrazole-4-thiocyanate compound is obtained with high selectivity. The method belongs to a green method for efficiently synthesizing 5-aminopyrazole-4-thiocyanate compounds.
In the examples, the 5-aminopyrazole and thiocyanate are both analytically pure reagents purchased directly from Yu Annai Ji Chemie, jiu Ding Chemie, alatine and Alamas, and the solvents or eluents used were purchased from Guo Yao Cheng without additional treatment.
Example 1
A10 mL undivided cell was charged with 3-methyl-1-phenyl-1H-pyrazol-5-amine (0.3 mmoL,52.0 mg), potassium thiocyanate (0.6 mmol,58.3 mg), acetic acid (0.3 mmol,18.2 mg), acetonitrile (2.5 mL), and water (0.5 mL), a platinum sheet electrode served as both anode and cathode, and the reaction was stirred at room temperature with energization (I=5mA) and was followed by TLC. After the completion of the reaction, the residue obtained by spin-drying was subjected to a column chromatography using an ethyl acetate/petroleum ether system as an eluent to obtain the product 3-methyl-1-phenyl-4-thiocyano-1H-pyrazol-5-amine compound in 94% yield.
The resulting product 3-methyl-1-phenyl-4-thiocyano-1H-pyrazol-5-amine was subjected to structural analysis by a nuclear magnetic resonance spectrometer, and the results are shown in FIGS. 1 to 2. FIG. 1 is a schematic illustration of the 3-methyl-1-phenyl-4-thiocyano-1H-pyrazol-5-amine product prepared in example 1 of the present invention 1 H nuclear magnetic resonance [ ] 1 H-NMR) spectra; FIG. 2 is a schematic illustration of the 3-methyl-1-phenyl-4-thiocyano-1H-pyrazol-5-amine product prepared in example 1 of the invention 13 C nuclear magnetic resonance 13 C-NMR) spectrum. 1 H NMR(DMSO-d 6 ,400MHz,ppm):δ＝7.53-7.49(m,4H),7.41-7.36(m,1H),6.34(br,2H),2.19(s,3H)； 13 C NMR(DMSO-d 6 ,100MHz,ppm):δ＝150.6,150.3,138.3,129.4,127.2,123.4,112.4,75.1,12.0。
Example 2
A10 mL undivided cell was charged with 3-tert-butyl-1-phenyl-1H-pyrazol-5-amine (0.3 mmoL,64.6 mg), potassium thiocyanate (0.6 mmol,58.3 mg), acetic acid (0.3 mmol,18.2 mg), acetonitrile (2.5 mL) and water (0.5 mL), a platinum sheet electrode served as both anode and cathode, and the reaction was stirred at room temperature with energization (I=5mA) and was followed by TLC. After the completion of the reaction, the residue obtained by spin-drying was subjected to a column chromatography using an ethyl acetate/petroleum ether system as an eluent to obtain the product 3-tert-butyl-1-phenyl-4-thiocyano-1H-pyrazol-5-amine compound in 91% yield.
The resulting product 3-tert-butyl-1-phenyl-4-thiocyano-1H-pyrazol-5-amine was subjected to structural analysis by a nuclear magnetic resonance spectrometer, and the results are shown in FIGS. 3 to 4. FIG. 3 is a schematic illustration of 3-tert-butyl-1-phenyl-4-thiocyano-1H prepared in example 2 of the present invention-pyrazol-5-amine products 1 H nuclear magnetic resonance [ ] 1 H-NMR) spectra; FIG. 4 is a schematic illustration of the 3-tert-butyl-1-phenyl-4-thiocyano-1H-pyrazol-5-amine product prepared in example 2 of the invention 13 C nuclear magnetic resonance 13 C-NMR) spectrum. 1 H NMR(CDCl 3 ,400MHz,ppm):δ＝7.53-7.47(m,4H),7.40-7.36(m,1H),4.44(br,2H),1.48(s,9H)； 13 C NMR(CDCl 3 ,100MHz,ppm):δ＝161.0,149.5,137.9,129.7,128.0,123.8,111.5,74.8,33.4,29.2。
Example 3
1, 3-diphenyl-1H-pyrazol-5-amine (0.3 mmoL,70.5 mg), potassium thiocyanate (0.6 mmole, 58.3 mg), acetic acid (0.3 mmole, 18.2 mg), acetonitrile (2.5 mL) and water (0.5 mL) were placed in a 10mL undivided electrolytic cell, and a platinum sheet electrode was used as both the anode and the cathode, and the reaction was stirred by energizing (I=5mA) at room temperature, followed by TLC. After the reaction, the residue obtained by spin-drying was subjected to a column chromatography using an ethyl acetate/petroleum ether system as an eluent to obtain the product 1, 3-diphenyl-4-thiocyano-1H-pyrazol-5-amine compound in 80% yield.
The resulting 1, 3-diphenyl-4-thiocyano-1H-pyrazol-5-amine product was subjected to structural analysis by a nuclear magnetic resonance spectrometer, the results of which are shown in FIGS. 5 to 6, and FIG. 5 is a 1, 3-diphenyl-4-thiocyano-1H-pyrazol-5-amine product prepared in example 3 of the present invention 1 H nuclear magnetic resonance [ ] 1 H-NMR) spectra; FIG. 6 is a schematic illustration of the 1, 3-diphenyl-4-thiocyano-1H-pyrazol-5-amine product prepared in example 3 of the invention 13 C nuclear magnetic resonance 13 C-NMR) spectrum. 1 H NMR(CDCl 3 ,400MHz,ppm):δ＝7.92-7.89(m,2H),7.59-7.42(m,8H),4.58(br,2H)； 13 C NMR(CDCl 3 ,100MHz,ppm):δ＝152.7,149.4,137.6,131.3,129.8,128.9,128.5,128.5,127.9,124.0,111.2,76.0。
Example 4
1-phenyl-1H-pyrazol-5-amine (0.3 mmoL,47.7 mg), potassium thiocyanate (0.6 mmol,58.3 mg), acetic acid (0.3 mmol,18.2 mg), acetonitrile (2.5 mL) and water (0.5 mL) were placed in a 10mL undivided electrolytic cell, and a platinum sheet electrode was used as both the anode and the cathode, and the reaction was stirred at room temperature by energizing (I=5mA) and followed by TLC. After the completion of the reaction, the residue obtained by spin-drying was subjected to chromatography using ethyl acetate/petroleum ether system as eluent to obtain the product 1-phenyl-4-thiocyano-1H-pyrazol-5-amine compound in 77% yield.
The resulting product 1-phenyl-4-thiocyano-1H-pyrazol-5-amine was subjected to structural analysis by a nuclear magnetic resonance spectrometer, and the results are shown in FIGS. 7 to 8. FIG. 7 is a schematic illustration of the 1-phenyl-4-thiocyano-1H-pyrazol-5-amine product prepared in example 4 of the invention 1 H nuclear magnetic resonance [ ] 1 H-NMR) spectra; FIG. 8 is a schematic illustration of the 1-phenyl-4-thiocyano-1H-pyrazol-5-amine product prepared in example 4 of the invention 13 C nuclear magnetic resonance 13 C-NMR) spectrum. 1 HNMR(CDCl 3 ,400MHz,ppm):δ＝7.59(s,1H),7.55-7.50(m,4H),7.46-7.42(m,1H),4.50(br,2H)； 13 C NMR(CDCl 3 ,100MHz,ppm):δ＝148.1,143.5,137.7,129.8,128.6,123.9,111.0,77.7。
Example 5
3-methyl-1- (p-methyl) phenyl-1H-pyrazol-5-amine (0.3 mmoL,56.1 mg), potassium thiocyanate (0.6 mmol,58.3 mg), acetic acid (0.3 mmol,18.2 mg), acetonitrile (2.5 mL) and water (0.5 mL) were placed in a 10mL undivided electrolytic cell, and a platinum sheet electrode was used as both the anode and the cathode, and the reaction was stirred at room temperature by energizing (I=5mA) and detected by TLC. After the completion of the reaction, the residue obtained by spin-drying was subjected to a column chromatography using an ethyl acetate/petroleum ether system as an eluent to obtain the product 3-methyl-1- (p-methyl) phenyl-4-thiocyano-1H-pyrazol-5-amine compound in a yield of 85%.
The obtained product 3-methyl-1- (p-methyl) phenyl-4-thiocyano-1H-pyrazol-5-amine was subjected to structural analysis, and the results are shown in FIGS. 9 to 10. FIG. 9 is a schematic illustration of the 3-methyl-1- (p-methyl) phenyl-4-thiocyano-1H-pyrazol-5-amine product prepared in example 5 of the present invention 1 H nuclear magnetic resonance [ ] 1 H-NMR) spectra; FIG. 10 is a schematic illustration of the 3-methyl-1- (p-methyl) phenyl-4-thiocyano-1H-pyrazol-5-amine product prepared in example 5 of the present invention 13 C nuclear magnetic resonance 13 C-NMR) spectrum. 1 H NMR(CDCl 3 ,400MHz,ppm):δ＝7.35-7.32(m,2H),7.28(d,J＝8.0Hz,2H),4.43(br,2H),2.40(s,3H),2.32(s,3H)； 13 C NMR(CDCl 3 ,100MHz,ppm):δ＝151.4,148.4,138.3,135.1,130.2,123.8,111.0,76.8,21.1,12.1。
Example 6
A10 mL undivided cell was charged with tert-butyl-5-amino-3-methyl-1H-pyrazole-1-carboxylate (0.3 mmoL,59.1 mg), potassium thiocyanate (0.6 mmol,58.3 mg), acetic acid (0.3 mmol,18.2 mg), acetonitrile (2.5 mL) and water (0.5 mL), the platinum sheet electrode served as both anode and cathode, and the reaction was stirred at room temperature with electricity (I=5mA) and monitored by TLC. After the reaction, the residue obtained by spin-drying was subjected to a column chromatography using an ethyl acetate/petroleum ether system as an eluent to obtain a product tert-butyl-5-amino-3-methyl-4-thiocyano-1H-pyrazole-1-carboxylate compound in 54% yield.
The structure analysis of the obtained product tert-butyl-5-amino-3-methyl-4-thiocyano-1H-pyrazole-1-carboxylic acid ester was carried out by a nuclear magnetic resonance spectrometer, and the results are shown in FIGS. 9 to 10. FIG. 9 is a schematic illustration of the tert-butyl-5-amino-3-methyl-4-thiocyano-1H-pyrazole-1-carboxylate product prepared in example 5 of the present invention 1 H nuclear magnetic resonance [ ] 1 H-NMR) spectra; FIG. 10 is a schematic illustration of the tert-butyl-5-amino-3-methyl-4-thiocyano-1H-pyrazole-1-carboxylate product prepared in example 5 of the present invention 13 C nuclear magnetic resonance 13 C-NMR) spectrum. 1 H NMR(CDCl 3 ,400MHz,ppm):δ＝6.05(br,2H),2.30(s,3H),1.65(s,9H)； 13 C NMR(CDCl 3 ,100MHz,ppm):δ＝154.0,153.3,149.8,110.1,86.6,76.5,27.9,12.5。
The energizing stirring reaction time in the embodiment of the invention can be arbitrary, and the 5-aminopyrazole-4-thiocyanate compound can be prepared only by energizing, the optimal energizing time is about 5 hours, and the yield of the obtained product is highest. The 5-aminopyrazole-4-thiocyanate compound can be prepared at any time, the yield is only changed, the yield gradually increases from the beginning of electrifying to 5h, and when the yield is more than 5h, the yield is reduced, which is possibly the result of the fact that the generated product is converted into other byproducts due to the overlong electrifying catalysis time.
The foregoing has shown and described the basic principles and main features of the present invention and the advantages of the present invention. It will be understood by those skilled in the art that the present invention is not limited to the embodiments described above, and that the above embodiments and descriptions are merely illustrative of the principles of the present invention, and various changes and modifications may be made without departing from the spirit and scope of the invention, which is defined in the appended claims. The scope of the invention is defined by the appended claims and equivalents thereof.

Claims (7)

1. An electrochemical synthesis method of a 5-aminopyrazole-4-thiocyanate compound is characterized by comprising the following steps:
(1) Electrocatalytic reaction: respectively adding thiocyanate, 5-aminopyrazole compounds, acid and solvent into a reaction tank, installing a catalytic electrode, and electrifying and stirring for reaction;
(2) And (3) separating and purifying: separating and purifying the solution after the electrocatalytic reaction is completed to obtain a 5-aminopyrazole-4-thiocyanate compound;
the 5-aminopyrazole-4-thiocyanate compound has a structure shown as follows:
wherein R is 1 Is hydrogen, C 1 ～C 5 Alkyl, aryl;R 2 is aryl or ester;
the thiocyanate is one of potassium thiocyanate, ammonium thiocyanate and sodium thiocyanate;
the 5-aminopyrazole compound has a structure shown as follows:
wherein R is 1 Is hydrogen, C 1 ～C 5 Alkyl, aryl; r is R 2 Is aryl or ester;
the solvent is acetonitrile and water;
the current i=5ma of the energized stirring reaction.
2. The electrochemical synthesis method according to claim 1, wherein: the mass ratio of the 5-aminopyrazole compound to the thiocyanate is 1:1-1:4.
3. The electrochemical synthesis method according to claim 1, wherein: the initial concentration of the 5-aminopyrazole compound is 0.05-0.2 mol/L.
4. The electrochemical synthesis method according to claim 1, wherein: the acid is one of acetic acid, benzoic acid, hydrochloric acid, sulfuric acid and diphenyl phosphoric acid, and the mass of the acid is 30-120% of that of the 5-aminopyrazole compound.
5. The electrochemical synthesis method according to claim 1, wherein: the temperature of the stirring reaction is 0-80 ℃.
6. The electrochemical synthesis method according to claim 1, wherein: the electrode is a conventional commercial electrode material.
7. The electrochemical synthesis method according to claim 1, wherein: the separation and purification method is one of column chromatography, liquid chromatography, distillation and recrystallization.
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CN108002969A (en) * 2017-12-01 2018-05-08 赣南师范大学 A kind of preparation method of thiocyanate ester compound

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