Method for photocatalytic synthesis of diaryl hydrazine compounds
By using a photocatalytic synthesis method, which involves reacting a specific photosensitizer and a basic reagent under visible light, the problems of high catalyst cost and limited substituent compatibility in existing diaryl synthesis methods have been solved. This method enables the efficient synthesis of diaryl hydrazine compounds and has promising application prospects.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- BENGBU COLLEGE
- Filing Date
- 2025-12-26
- Publication Date
- 2026-05-12
AI Technical Summary
Existing methods for the synthesis of diaryl compounds suffer from high catalyst costs and limited substituent compatibility, making it difficult to efficiently construct diarylhydrazine compounds.
A photocatalytic synthesis method was adopted, using azobenzene compounds, alkyl NHP ester reagents, photosensitizers, and basic reagents to react under visible light to generate diarylhydrazine compounds. Specifically, 2,4,5,6-tetra(carbazole-9-yl)-1,3-dicyanobenzene and bis[2-(2,4-difluorophenyl)-5-trifluoromethylpyridine][2-2'-bi(4-tert-butylpyridine)]iridium hexafluorophosphate were used as photosensitizers, N,N-diisopropylethylamine and potassium phosphate were used as basic reagents, and tetrahydrofuran was used as a solvent. The reaction conditions were mild and the substrate applicability was broad.
The method achieves efficient synthesis of diarylhydrazine compounds, with readily available raw materials, simple operation, mild reaction, and wide substrate applicability. The synthesis method has good application prospects.
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Abstract
Description
Technical Field
[0001] This invention relates to the field of organic synthesis technology, and specifically to a method for photocatalytic synthesis of diarylhydrazine compounds. Background Technology
[0002] Diarylhydrazines are a class of compounds of significant value in medicinal chemistry, functional materials, and organic synthesis. Their derivatives have shown promising bioactivity in the development of anticancer, anti-inflammatory, and antidiabetic drugs. However, existing methods for the synthesis of diaryl compounds still face many limitations. Traditional methods typically rely on the coupling reaction of aryl halides with hydrazine reagents, or use azo compounds as starting materials to achieve a reduction reaction via metal reducing agents (such as SnCl2, NaBH4, etc.).
[0003] In recent years, photocatalysis has attracted widespread attention in organic synthesis as a mild, green, and tunable reaction method. Although existing reports on the photocatalytic reduction of azo compounds can achieve the transformation of certain systems, they are mostly limited to specific substrates or require special catalytic systems, and still have shortcomings such as high catalyst cost and limited substituent compatibility.
[0004] Therefore, developing a novel photocatalytic method that is mild, has a broad substrate range, and can efficiently construct diarylhydrazine compounds is of great significance for expanding the synthetic strategies and applications of these compounds. Summary of the Invention
[0005] The technical problem to be solved by this invention is how to efficiently construct diarylhydrazine compounds.
[0006] The present invention solves the above-mentioned technical problems through the following technical means: A method for photocatalytic synthesis of diarylhydrazine compounds includes the following steps: mixing an azobenzene compound, an alkyl NHPI ester reagent, a photosensitizer, a basic reagent, and a solvent, and reacting the mixture under visible light irradiation to obtain the diarylhydrazine compound; The photosensitizer is one or a mixture of two of 2,4,5,6-tetra(carbazole-9-yl)-1,3-dicyanophenyl and bis[2-(2,4-difluorophenyl)-5-trifluoromethylpyridine][2-2'-bi(4-tert-butylpyridine)]iridium hexafluorophosphate; the alkaline reagent is one or a mixture of N,N-diisopropylethylamine, potassium phosphate, and 1,8-diazabicyclo[5.4.0]undec-7-ene DBU. The structural formula of the azobenzene compound is as follows: ; The structural formula of the alkyl NHP ester reagent is as follows:
[0007] The structural formula of the diarylhydrazine compounds is as follows: ; In the formula, R is selected from one or more of hydrogen, alkyl, and halogen, and R' is selected from cyclohexyl, adamantyl, 1-([1,1'-biphenyl]-4-yl)propane-1-one ( One or more of the following.
[0008] Preferably, the alkyl group (including straight-chain, branched and cycloalkyl) has one or more carbon atoms from 1 to 6, and the halogen is one or more of fluorine, chlorine, bromine and iodine.
[0009] Preferably, the azobenzene compound has one of the following structural formulas: , , .
[0010] Preferably, the alkyl NHP ester reagent has one of the following structural formulas: , , .
[0011] Preferably, the diarylhydrazine compound has one of the following structural formulas: , , ; In the formula, R is selected from one or more of hydrogen, alkyl, and halogen.
[0012] Preferably, the molar ratio of the azobenzene compound to the alkyl NHPI ester reagent is 1:1 to 5; the molar ratio of the azobenzene compound to the photosensitizer is 1:0.01 to 0.10; and the molar ratio of the azobenzene compound to the basic reagent is 1:1 to 3.
[0013] Preferably, the molar ratio of the azobenzene compound to the alkyl NHPI ester reagent is 1:2; the molar ratio of the azobenzene compound to the photosensitizer is 1:0.04; and the molar ratio of the azobenzene compound to the basic reagent is 1:2.5.
[0014] Preferably, the solvent is at least one selected from tetrahydrofuran, acetonitrile, toluene, dichloroethane, methanol, N,N-dimethylformamide, chloroform, dioxane, and dichloromethane.
[0015] Preferably, the wavelength of the visible light is 380~525 nm.
[0016] Preferably, the visible light wavelength is at least one of 380 nm to 390 nm, 420 nm to 430 nm, 450 nm to 455 nm, and 520 nm to 525 nm.
[0017] Preferably, the reaction temperature is 10 ℃ to 80 ℃, and the reaction time is 8 h to 18 h.
[0018] Preferably, the reaction is carried out at room temperature.
[0019] Preferably, the ratio of the azobenzene compound to the solvent is 0.1 mmol: 2 mL.
[0020] Preferably, the reaction is carried out at a stirring speed of 300 rpm to 700 rpm.
[0021] Preferably, the reaction product is further separated and purified after the reaction is completed.
[0022] Preferably, the specific operations of separation and purification include: extracting the reaction product with dichloromethane, drying with anhydrous Na2SO4, distilling under reduced pressure, and purifying the crude product obtained by reduced pressure distillation by column chromatography.
[0023] Preferably, the eluent used in the column chromatography is composed of petroleum ether and ethyl acetate in a volume ratio of 1:0 to 20:1.
[0024] This invention also proposes a diarylhydrazine compound with the following structural formula: or .
[0025] The principle of this invention is as follows: Under visible light irradiation, alkyl NHPI ester reagents interact with photocatalysts to generate alkyl radicals, which then undergo a free radical tandem process with various azobenzenes to generate the final diarylhydrazine compounds.
[0026] The beneficial effects of this invention are: it synthesizes a series of diarylhydrazine compounds and drug molecules containing different substituents. The synthetic method has advantages such as readily available raw materials, simple operation, mild reaction, and wide substrate applicability. Attached Figure Description
[0027] Figure 1 The hydrogen spectrum of the target product obtained in Example 1 of this invention; Figure 2 The carbon spectrum of the target product obtained in Example 1 of this invention; Figure 3 The hydrogen spectrum of the target product obtained in Example 2 of this invention; Figure 4 The carbon spectrum of the target product obtained in Example 2 of this invention; Figure 5 The hydrogen spectrum of the target product obtained in Example 3 of this invention; Figure 6 The carbon spectrum of the target product obtained in Example 3 of this invention; Figure 7 The hydrogen spectrum of the target product obtained in Example 4 of this invention; Figure 8 The carbon spectrum of the target product obtained in Example 4 of this invention; Figure 9 The hydrogen spectrum of the target product obtained in Example 5 of this invention; Figure 10 This is the carbon spectrum of the target product obtained in Example 5 of the present invention. Detailed Implementation
[0028] To make the objectives, technical solutions, and advantages of the embodiments of the present invention clearer, the technical solutions of the embodiments of the present invention will be clearly and completely described below in conjunction with the embodiments of the present invention. Obviously, the described embodiments are only some embodiments of the present invention, not all embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without creative effort are within the scope of protection of the present invention.
[0029] Unless otherwise specified, all test materials and reagents used in the following examples are commercially available.
[0030] Unless otherwise specified in the embodiments, the techniques or conditions described in the literature in this field or in accordance with the product manual may be followed.
[0031] Substituted azobenzene and The synthetic method was described in Angew. Chem. Int. Ed. 2010, 49, 6174-6177, and specifically included the following steps: In a round-bottom flask equipped with a stir bar, CuBr (4.2 mg, 0.03 mmol), pyridine (7.1 mg, 0.09 mmol), and m-chloroaniline or p-bromoaniline (1 mmol) were dissolved in toluene (4 mL). The reaction mixture was stirred vigorously at 60 °C for 20 hours. After cooling to room temperature, the mixture was concentrated under vacuum, and the residue was purified by column chromatography (eluent: petroleum ether) to obtain substituted azobenzene.
[0032] Alkyl NHP ester raw materials , The synthetic method comprises the following steps: In a round-bottom flask, carboxylic acid (cyclohexylcarboxylic acid or 3-(4-biphenylcarbonyl)propionic acid) (2.0 mmol), N-hydroxyphthalimide (326.3 mg, 2.0 mmol), and DMAP (12.2 mg, 0.1 mmol) are added. Dichloromethane (10 mL) is added, and the mixture is stirred vigorously. DCC (22.7 mg, 1.1 mmol) is then added, and stirring continues until the acid is completely consumed (as detected by thin-layer chromatography). The residue is extracted multiple times with water, dried over anhydrous Na₂SO₄, concentrated under vacuum, and purified by column chromatography (eluent: petroleum ether and ethyl acetate, v / v ratio 20–5:1) to obtain the target alkyl NHPI ester starting material.
[0033] adamantyl NHP ester raw material The synthesis includes the following steps: A solution of N-hydroxyphthalimide (5.0 g, 30.7 mmol), triethylamine (3.1 g, 30.7 mmol), and 4-dimethylaminopyridine (0.34 g, 2.8 mmol) in dichloromethane (70 mL) was cooled in an ice-water bath. A dichloromethane solution of adamantyl chloride (7.8 g, 39.5 mmol) was slowly added dropwise. After stirring for 3 hours following the addition, the residue was extracted repeatedly with water and dried over anhydrous sodium sulfate. The crude product was eluted with dichloromethane and purified by column chromatography to obtain the final product.
[0034] Example 1 A diarylhydrazine compound, the preparation method of which includes the following steps: 0.1 mmol of azobenzene 0.2 mmol of alkyl NHP ester 0.004 mmol of 2,4,5,6-tetra(carbazole-9-yl)-1,3-dicyanophenyl (4CZIPN) and 0.25 mmol of N,N-diisopropylethylamine were dispersed in 2 mL of dichloromethane and reacted at room temperature for 12 h under visible light at a wavelength of 380 nm–390 nm with stirring at 500 rpm. The reaction solution was extracted three times with dichloromethane, and the combined organic phases were dried over anhydrous sodium sulfate, filtered, and the filtrate was subjected to vacuum distillation. The crude product obtained by vacuum distillation was purified by column chromatography using petroleum ether as the eluent to obtain diarylhydrazine compounds (yield: 72%).
[0035] The proton and carbon spectra of the target product in this embodiment are as follows: Figure 1 and Figure 2 As shown, the spectral data is as follows: 1H NMR (600 MHz, Chloroform- d ) δ 7.23 –7.19 (m, 4H), 6.89 –6.87 (m,4H), 6.79 (t, J = 7.2 Hz, 2H), 5.40 (s, 1H), 3.84 – 3.79 (m, 1H), 1.92 –1.82(m, 4H), 1.67 (d, J = 12.6 Hz, 1H), 1.46 – 1.33 (m, 3H), 1.31 –1.28 (m, 1H), 1.18 – 1.10 (m, 1H). 13 C NMR (151 MHz, CDCl3) δ 149.50, 149.37, 129.26, 129.24, 119.04, 118.69, 113.67, 111.77, 59.51, 25.75. The mass spectrometry data of the diarylhydrazine compounds in this embodiment are as follows: HRMS (APCI) calcd for C 18 H 23 N2[M+H] + Found: 267.1856. In summary, the structural formula of the target product in this embodiment is as follows: .
[0036] Example 2 A diarylhydrazine compound, the preparation method of which includes the following steps: 0.1 mmol 0.2 mmol 0.004 mmol of 2,4,5,6-tetra(carbazole-9-yl)-1,3-dicyanophenylbenzene (abbreviated as 4CZIPN) and 0.25 mmol of N,N-diisopropylethylamine were dispersed in 2 mL of dichloromethane and reacted at room temperature for 12 h under visible light at a wavelength of 380 nm to 390 nm with stirring at 500 rpm. The reaction solution was extracted three times with dichloromethane, and the combined organic phases were dried over anhydrous sodium sulfate, filtered, and the filtrate was subjected to vacuum distillation. The crude product obtained by vacuum distillation was purified by column chromatography using petroleum ether as the eluent to obtain diarylhydrazine compounds (yield: 72%).
[0037] The proton and carbon spectra of the target product in this embodiment are as follows: Figure 3 and Figure 4 As shown, the spectral data is as follows: 1 H NMR (600 MHz, Chloroform- d ) δ 7.13 – 7.08 (m, 2H), 6.83 (d, J = 6.8Hz, 2H), 6.77 (t, J = 9.2 Hz, 2H), 6.72 – 6.68 (m, 2H), 5.46 (s, 1H), 3.77 –3.73 (m, 1H), 1.92 – 1.83 (m, 4H), 1.67 (d, J = 12.9 Hz, 1H), 1.57 (s, 1H),1.37 – 1.33 (m, 2H), 1.27 (d, J = 18.4 Hz, 1H), 1.15 – 1.08 (m, 1H). 13 C NMR (151 MHz, CDCl3) δ 150.36, 150.19, 135.23, 130.37, 130.32, 119.36, 119.05, 113.69, 111.90, 111.74, 109.92, 60.01, 25.60. The mass spectrometry data of the diarylhydrazine compounds in this embodiment are as follows: HRMS (APCI) calcd for C 18 H 21 Cl2N2, [M+H] + Found: 355.1077, Found: 355.1076. In summary, the structural formula of the target product in this embodiment is as follows: .
[0038] Example 3 A diarylhydrazine compound, the preparation method of which includes the following steps: 0.1 mmol 0.2 mmol 0.004 mmol of 2,4,5,6-tetra(carbazole-9-yl)-1,3-dicyanophenyl (4CZIPN) and 0.25 mmol of N,N-diisopropylethylamine were dispersed in 2 mL of dichloromethane and reacted at room temperature for 12 h under visible light at a wavelength of 380 nm–390 nm with stirring at 500 rpm. The reaction solution was extracted three times with dichloromethane, and the combined organic phases were dried over anhydrous sodium sulfate, filtered, and the filtrate was subjected to vacuum distillation. The crude product obtained by vacuum distillation was purified by column chromatography using petroleum ether as the eluent to obtain diarylhydrazine compounds (yield: 60%).
[0039] The proton and carbon spectra of the target product in this embodiment are as follows: Figure 5 and Figure 6 As shown, the spectral data is as follows: 1 H NMR (600 MHz, Chloroform-d) δ 7.22 – 7.19 (m, 4H), 6.63 (d, J = 8.4Hz, 4H), 5.32 (s, 1H), 3.65 (t, J = 10.8 Hz, 1H), 1.75 – 1.74 (m, 3H), 1.59(d, J = 13.2 Hz, 1H), 1.51 (d, J = 6.6 Hz, 1H), 1.30 – 1.24 (m, 3H), 1.20 (d,J = 18.6 Hz, 2H), 1.03 (s, 1H). 13 C NMR (151 MHz, CDCl3) δ 148.12, 148.08, 132.09, 132.05, 115.40, 113.43, 111.07, 110.82, 59.86, 25.62. The mass spectrometry data of the diarylhydrazine compounds in this embodiment are as follows: HRMS (APCI) calcd for C 18 H 21 Br2N2, [M+H] + : 423.0066, Found: 423.0066. In summary, the structural formula of the target product in this embodiment is as follows: .
[0040] Example 4 A diarylhydrazine compound, the preparation method of which includes the following steps: 0.1 mmol 0.2 mmol 0.004 mmol of 2,4,5,6-tetra(carbazole-9-yl)-1,3-dicyanophenyl (4CZIPN) and 0.25 mmol of N,N-diisopropylethylamine were dispersed in 2 mL of dichloromethane and reacted at room temperature for 12 h under visible light at a wavelength of 380 nm–390 nm and a stirring speed of 500 rpm. The reaction solution was extracted three times with dichloromethane, and the combined organic phases were dried over anhydrous sodium sulfate, filtered, and the filtrate was subjected to vacuum distillation. The crude product obtained by vacuum distillation was purified by column chromatography using a mixture of petroleum ether and ethyl acetate in a volume ratio of 1:0–20:1 to obtain diarylhydrazine compounds (yield: 72%).
[0041] The proton and carbon spectra of the target product in this embodiment are as follows: Figure 7 and 8 As shown, the spectral data is as follows: 1 H NMR (600 MHz, Chloroform-d) δ 7.26 – 7.22 (m, 4H), 7.13 – 7.08 (m,3H), 6.92 (d, J = 7.8 Hz, 2H), 6.66 (t, J = 7.2 Hz, 1H), 5.75 (s, 1H), 2.06(s, 3H), 1.80 (s, 5H), 1.63 – 1.55 (m, 7H). 13 C NMR (151 MHz, Chloroform-d) δ 149.59, 147.34, 128.81, 128.05, 127.15, 125.21, 118.34, 112.72, 58.69, 39.64, 36.54, 29.56. The mass spectrometry data of the compound in this embodiment are as follows: HRMS (APCI) calcd for C 22 H 27 N2, [M+H] + Found: 319.2169, Found: 319.2165 In summary, the structural formula of the target product in this embodiment is as follows: .
[0042] Example 5 A diarylhydrazine compound, the preparation method of which includes the following steps: 0.1 mmol 0.2 mmol 0.004 mmol of 2,4,5,6-tetra(carbazole-9-yl)-1,3-dicyanophenyl (4CZIPN) and 0.25 mmol of N,N-diisopropylethylamine were dispersed in 2 mL of dichloromethane and reacted at room temperature for 12 h under visible light at a wavelength of 380 nm–390 nm and a stirring speed of 500 rpm. The reaction solution was extracted three times with dichloromethane, and the combined organic phases were dried over anhydrous sodium sulfate, filtered, and the filtrate was subjected to vacuum distillation. The crude product obtained by vacuum distillation was purified by column chromatography using a mixture of petroleum ether and ethyl acetate in a volume ratio of 1:0–9:1 to obtain diarylhydrazine compounds (yield: 65%).
[0043] The proton and carbon spectra of the target product in this embodiment are as follows: Figure 9 and Figure 10 As shown, the spectral data is as follows: 1 H NMR (600 MHz, Chloroform- d ) δ 7.96 (d, J = 8.4 Hz, 2H), 7.62 (dd, J = 19.2, 7.8 Hz, 4H), 7.46 (t, J = 7.8 Hz, 2H), 7.40 (d, J = 7.2 Hz, 1H), 7.24(t, J = 7.8 Hz, 2H), 7.18 (t, J = 7.8 Hz, 2H), 6.96 (d, J = 8.4 Hz, 2H), 6.83 –6.80 (m, 4H), 5.89 (s, 1H), 4.00 (t, J = 6.6 Hz, 2H), 3.40 (t, J = 6.0 Hz, 2H). 13 C NMR (151 MHz, Chloroform- d ) δ199.00, 149.24, 147.83, 145.89, 139.75, 135.40, 129.37, 129.34, 128.93, 128.64, 128.26, 127.23, 127.21, 119.75, 118.93, 112.97, 112.45, 47.41, 35.53. The mass spectrometry data of the diarylhydrazine compounds in this embodiment are as follows: HRMS (APCI) calcd for C 27 H 25 N₂O, [M+H] + Found: 393.1962, Found: 393.1961. In summary, the structural formula of the target product in this embodiment is as follows: .
[0044] Comparative Example 1 The difference from Example 1 is that the photosensitizer 2,4,5,6-tetra(carbazole-9-yl)-1,3-dicyanobenzene in Example 1 was replaced with 3,6-di-tert-butyl-9-trimethyl-10-phenylacridine perchlorate, 2',4',5',7'-tetrabromo-3',6'-dihydroxy-3H-spiro[isobenzofuran-1,9'-oxanthracene]-3-one or 2',4',5',7'-tetrabromo-3-oxo-3H-spirocyclic[isobenzofuran-1,9'-oxanthracene]-3',6'-bis(phenol) disodium salt, and the remaining steps were the same as in Example 1; no product was detected.
[0045] Replacing the photosensitizer 2,4,5,6-tetra(carbazole-9-yl)-1,3-dicyanophenyl in Example 1 with bis[2-(2,4-difluorophenyl)-5-trifluoromethylpyridine][2-2'-bi(4-tert-butylpyridine)]iridium hexafluorophosphate as a catalyst yields the product with a yield of 67%.
[0046] Comparative Example 2 The difference from Example 1 is that the alkaline substance N,N-diisopropylethylamine required for the reaction in Example 1 is replaced with one of sodium hydroxide, potassium carbonate, triethylamine, or sodium tert-butoxide. The remaining steps are the same as in Example 1, but only trace amounts of product are obtained or the product is not detected.
[0047] Replacing N,N-diisopropylethylamine in Example 1 with potassium phosphate or 1,8-diazabicyclo[5.4.0]undec-7-ene as the alkaline substance for the reaction yields the product, but the yield is significantly reduced to 36% and 24%, respectively.
[0048] Example 6 The difference from Example 1 is that the wavelength in Example 1 is replaced with one of the visible light wavelengths of 420-430 nm, 450-455 nm, and 520-525 nm. The remaining steps are the same as in Example 1, and the product can also be obtained, but the reaction yield will be significantly reduced, with yields of 52%, 60%, and 40%, respectively.
[0049] The above embodiments are only used to illustrate the technical solutions of the present invention, and are not intended to limit it. Although the present invention has been described in detail with reference to the foregoing embodiments, those skilled in the art should understand that modifications can still be made to the technical solutions described in the foregoing embodiments, or equivalent substitutions can be made to some of the technical features. Such modifications or substitutions do not cause the essence of the corresponding technical solutions to deviate from the spirit and scope of the technical solutions of the embodiments of the present invention.
Claims
1. A method for photocatalytic synthesis of diarylhydrazine compounds, characterized in that, Includes the following steps: A mixture of azobenzene compound, alkyl NHP ester reagent, photosensitizer, basic reagent and solvent is reacted under visible light to obtain diarylhydrazine compounds. The photosensitizer is one or a mixture of two of 2,4,5,6-tetra(carbazole-9-yl)-1,3-dicyanophenyl and bis[2-(2,4-difluorophenyl)-5-trifluoromethylpyridine][2-2'-bi(4-tert-butylpyridine)]iridium hexafluorophosphate; the alkaline reagent is one or a mixture of N,N-diisopropylethylamine, potassium phosphate, and 1,8-diazabicyclo[5.4.0]undec-7-ene. The structural formula of the azobenzene compound is as follows: ； The structural formula of the alkyl NHP ester reagent is as follows: The structural formula of the diarylhydrazine compounds is as follows: ； In the formula, R is selected from one or more of hydrogen, alkyl, and halogen, and R' is selected from one or more of cyclohexyl, adamantyl, and 1-([1,1'-biphenyl]-4-yl)propane-1-one.
2. The method for photocatalytic synthesis of diarylhydrazine compounds according to claim 1, characterized in that, The azobenzene compound has one of the following structural formulas: 、 、 。 3. The method for photocatalytic synthesis of diarylhydrazine compounds according to claim 1, characterized in that, The alkyl NHP ester reagent has one of the following structural formulas: 、 、 。 4. The method for photocatalytic synthesis of diarylhydrazine compounds according to claim 1, characterized in that, The structural formula of the diarylhydrazine compound is one of the following structural formulas: 、 、 ； In the formula, R is selected from one or more of hydrogen, alkyl, and halogen.
5. The method for photocatalytic synthesis of diarylhydrazine compounds according to claim 1, characterized in that, The molar ratio of the azobenzene compound to the alkyl NHPI ester reagent is 1:1~5; the molar ratio of the azobenzene compound to the photosensitizer is 1:0.01~0.10; and the molar ratio of the azobenzene compound to the basic reagent is 1:1~3.
6. The method for photocatalytic synthesis of diarylhydrazine compounds according to claim 1, characterized in that, The solvent is at least one selected from tetrahydrofuran, acetonitrile, toluene, dichloroethane, methanol, N,N-dimethylformamide, chloroform, dioxane, and dichloromethane.
7. The method for photocatalytic synthesis of diarylhydrazine compounds according to claim 1, characterized in that, The wavelength of the visible light is 380~525 nm.
8. The method for photocatalytic synthesis of diarylhydrazine compounds according to claim 1, characterized in that, The reaction temperature is 10 ℃ to 80 ℃, and the reaction time is 8 h to 18 h.
9. The method for photocatalytic synthesis of diarylhydrazine compounds according to any one of claims 1-8, characterized in that, The ratio of the azobenzene compound to the solvent is 0.1 mmol: 2 mL.
10. A diarylhydrazine compound, characterized in that, Its structural formula is or .