Preparation method and application of diselenide arylamine compound

Abstract

The invention discloses a preparation method and application of a double-selenium arylamine compound. The preparation method comprises the following steps: mixing a compound shown as a formula I, a compound shown as a formula II, a copper catalyst, an oxidizing agent and a solvent for reaction to obtain a compound shown as a formula III. The bis-selenium arylamine compound is prepared from the compound shown in the formula I and the compound shown in the formula II as raw materials through a one-step method, synthesis steps are simple, the raw materials are non-toxic, low in price and easy to obtain, and the synthesis method has the advantages of being good in functional group compatibility, high in atom economy and high in yield.

Description

Technical Field

[0001] The present invention relates to the technical field of organic synthesis, in particular to a preparation method of a bis-selenium aromatic amine compound and application thereof. Background Art

[0002] Aryl selenides are important intermediates widely used in the development of bioactive compounds, pharmaceuticals, and functional materials, exhibiting diverse pharmacological properties and biological activities. Compounds with C-Se bonds have a wide range of applications in functional polymer materials, pharmaceuticals, pesticides, and synthetic chemicals. Consequently, the synthesis of aryl selenides has attracted considerable attention, with C-Se bond formation being a major focus of synthetic chemistry research.

[0003] Previously reported synthesis methods for selenium-containing compounds have problems such as harsh reaction conditions, long reaction steps, the need to use equivalent amounts of toxic and hazardous reagents, poor selectivity of CH functionalization, and the fact that most products are monoselenide.

[0004] It is highly desirable to develop more efficient, green and environmentally friendly methods for synthesizing diselenide compounds. Summary of the Invention

[0005] The present invention aims to solve at least one of the technical problems existing in the prior art. To this end, the first aspect of the present invention provides a method for preparing a bis-selenium aromatic amine compound, which has the advantages of mild reaction conditions, good reaction selectivity, high product yield, and easy product separation.

[0006] The second aspect of the present invention also provides an application.

[0007] According to a first aspect of the present invention, a method for preparing a bis-selenium aromatic amine compound is provided, comprising the following steps:

[0008] The compound of formula I, the compound of formula II, a copper catalyst, an oxidant and a solvent are mixed and reacted to obtain a compound of formula III;

[0009] Wherein, the structural formulas of the compound of formula I, the compound of formula II and the compound of formula III are as follows:

[0010]

[0011] Wherein, R1 is selected from H, C 1～12 One of the alkyl, aromatic or heteroaromatic groups; X=C or O;

[0012] R2 is selected from C 1～12 Alkyl, C 1～12 Alkoxy, phenyl or C 1～6 an alkyl-substituted phenyl group;

[0013] R3 is selected from H or C 1～12of alkyl.

[0014] The method for preparing a bis-selenium aromatic amine compound provided in an embodiment of the present invention has at least the following beneficial effects:

[0015] The present invention uses a compound of formula I and a compound of formula II as raw materials to prepare a bis-selenium aromatic amine compound through a one-step method. Not only is the synthesis step simple, the raw materials are non-toxic, cheap and easily available, but the synthesis method also has the advantages of good functional group compatibility, high atom economy and high yield.

[0016] According to a preferred embodiment of the present invention, R1 is one or more substituents independently selected from H, C 1～6 of alkyl.

[0017] According to a preferred embodiment of the present invention, R2 is selected from C 1～6 Alkyl, C 1～6 Alkoxy, phenyl or C 1～6 an alkyl-substituted phenyl group.

[0018] According to a preferred embodiment of the present invention, the dotted line portion in the structural formula of the compound of formula I of the present invention indicates presence or absence; if the dotted line does not exist, R1 does not exist either; the ring formed by the dotted line includes a six-membered ring, a seven-membered ring or an eight-membered ring.

[0019] According to a preferred embodiment of the present invention, the oxidant includes at least one of iodine, iodized salt, persulfate or hydrogen peroxide.

[0020] According to a preferred embodiment of the present invention, the iodide salt includes at least one of sodium iodide, ammonium iodide, and potassium iodide.

[0021] According to a preferred embodiment of the present invention, the persulfate includes at least one of sodium persulfate, potassium persulfate, and ammonium persulfate.

[0022] According to a preferred embodiment of the present invention, the copper catalyst includes at least one of cupric chloride, cuprous chloride, cupric oxide, cuprous iodide, cupric bromide, copper acetate, copper sulfate, copper trifluoromethanesulfonate, and a nitrogen-doped carbon-supported copper catalyst.

[0023] According to a preferred embodiment of the present invention, the reaction temperature is 25-80°C.

[0024] According to a preferred embodiment of the present invention, the molar ratio of the compound of formula I to the compound of formula II is 1:(1-5).

[0025] According to a preferred embodiment of the present invention, the molar ratio of the copper catalyst to the compound of formula I is (0.02-0.08):1.

[0026] According to a preferred embodiment of the present invention, the molar ratio of the oxidant to the compound of formula I is (1-5):1.

[0027] According to a preferred embodiment of the present invention, the solvent is an organic solvent.

[0028] According to a preferred embodiment of the present invention, the organic solvent includes at least one of a nitrile solvent, an amide solvent, a pyridine solvent, an alcohol solvent and a sulfoxide solvent.

[0029] According to a preferred embodiment of the present invention, the nitrile solvent includes acetonitrile.

[0030] According to a preferred embodiment of the present invention, the amide solvent includes at least one of N-methylformamide, formamide, N-ethylformamide and N,N-dimethylformamide.

[0031] According to a preferred embodiment of the present invention, the pyridine solvent includes pyridine.

[0032] According to a preferred embodiment of the present invention, the alcohol solvent includes at least one of tert-amyl alcohol, isopropanol, isobutanol and methanol.

[0033] According to a preferred embodiment of the present invention, the sulfoxide solvent includes at least one of thionyl chloride, dimethyl sulfoxide, and diphenyl sulfoxide.

[0034] According to a preferred embodiment of the present invention, the reaction time is 1 to 24 hours.

[0035] According to a preferred embodiment of the present invention, the preparation method further comprises the following steps: after the reaction is completed, removing the solvent and purifying.

[0036] According to a preferred embodiment of the present invention, the purification method is column chromatography.

[0037] According to a preferred embodiment of the present invention, the stationary phase used in the column chromatography is silica gel, and the eluent used is a mixed solvent of petroleum ether and ethyl acetate, and the volume ratio of the petroleum ether to the ethyl acetate is petroleum ether:ethyl acetate=(5-30):1.

[0038] The second embodiment of the present invention further provides a use of a diselenylamine compound prepared by the preparation method described in the first aspect in the preparation of analgesic, antibacterial and antitumor drugs.

[0039] Definitions and General Terms

[0040] “C 1～12"Alkyl" means an alkyl group with a total carbon number of 1 to 12, including C 1～12 Straight chain alkyl, C 1～12 Branched alkyl and C 3～12 The cycloalkyl group may be, for example, a straight-chain alkyl group having 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms, a branched-chain alkyl group having 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms, or a cycloalkyl group having 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, cyclopropyl, methylcyclopropyl, ethylcyclopropyl, cyclopentyl, methylcyclopentyl, cyclohexyl, etc. 1～6 The term "alkyl" has the same meaning as "alkyl", except that the total number of carbon atoms is 1 to 6.

[0041] “C 1～12 "Alkoxy" means an alkoxy group having a total carbon number of 1 to 12, including C 1～12 Straight chain alkoxy, C 1～12 Branched alkoxy and C 3～12 The cycloalkoxy group may be, for example, a straight chain alkoxy group having 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms, a branched chain alkoxy group having 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms, or a cycloalkoxy group having 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms, such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, n-pentoxy, isopentoxy, n-hexyloxy, cyclopropyloxy, cyclohexyloxy, etc. 1～6 The "alkoxy" has the same meaning, except that the total number of carbon atoms is 1 to 6.

[0042] “C 5～8 The term "heterocyclic group" refers to a heterocyclic group having 5 to 8 carbon atoms, wherein at least one of the ring carbon atoms is substituted by oxygen or nitrogen.

[0043] Other features and advantages of the present invention will be set forth in the description which follows, and in part will be obvious from the description, or may be learned by practice of the present invention. BRIEF DESCRIPTION OF THE DRAWINGS

[0044] The above and / or additional aspects and advantages of the present invention will become apparent and readily understood from the following description of the embodiments with reference to the accompanying drawings, in which:

[0045] Figure 1 This is the hydrogen spectrum of the product prepared in Example 1;

[0046] Figure 2 The carbon spectrum of the product prepared in Example 1;

[0047] Figure 3 This is the hydrogen spectrum of the product prepared in Example 2;

[0048] Figure 4 This is the carbon spectrum of the product prepared in Example 2;

[0049] Figure 5 This is the hydrogen spectrum of the product prepared in Example 3;

[0050] Figure 6 This is the carbon spectrum of the product prepared in Example 3;

[0051] Figure 7 This is the hydrogen spectrum of the product prepared in Example 4;

[0052] Figure 8 This is the carbon spectrum of the product prepared in Example 4;

[0053] Figure 9 This is the hydrogen spectrum of the product prepared in Example 5;

[0054] Figure 10 This is the carbon spectrum of the product prepared in Example 5;

[0055] Figure 11 This is the hydrogen spectrum of the product prepared in Example 6;

[0056] Figure 12 This is the carbon spectrum of the product prepared in Example 6. DETAILED DESCRIPTION

[0057] The following are specific embodiments of the present invention, and the technical solutions of the present invention are further described in conjunction with the embodiments, but the present invention is not limited to these embodiments.

[0058] Unless otherwise specified, the reagents, methods and equipment used in the present invention are conventional reagents, methods and equipment in the art.

[0059] Example 1

[0060] This example provides a method for preparing a bis-selenium aromatic amine compound, the structural formula of which is as follows, comprising the following steps:

[0061]

[0062] 0.2 mmol of tetrahydroquinoline, 0.6 mmol of diphenyl diselenide, 10 mg of copper sulfate, 0.2 mmol of iodine, and 2 ml of dimethyl sulfoxide were added to a 50 mL Schlenk tube equipped with a magnetic stirrer. Under a 1 atm oxygen atmosphere (using an oxygen balloon), the Schlenk tube was closed and heated at 60°C for 16 h. After cooling to room temperature, the reaction mixture was filtered. Water (10 mL) and ethyl acetate (30 mL) were added to the resulting layered solution, and the aqueous layer was extracted with ethyl acetate (2 x 10 mL). The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated in vacuo. The desired product was then isolated and purified by column chromatography using silica gel as the stationary phase and a mixed solvent of petroleum ether and ethyl acetate (petroleum ether:ethyl acetate = 30:1, v / v) as the eluent. The yield of the desired product was 77%.

[0063] The hydrogen and carbon spectra of the obtained products are shown as follows: Figure 1 and Figure 2 The structural characterization data are as follows:

[0064] 1 H NMR(400MHz,Chloroform-d)δ7.80(s,1H),7.40–7.34(m,3H),7.25(dq,J=13.8 ,7.4,6.8Hz,8H),3.40–3.31(m,2H),2.81(t,J=6.3Hz,2H),2.00–1.86(m,2H);

[0065] 13 C NMR (101MHz, Chloroform-d) δ146.4,143.9,138.7,134.5,131.7,129.9,129.3,129.2,129.1,126.2,126.0,122.6,113.1,111.9,42.0,27.5,21.4.

[0066] HRMS(ESI):Calcd.For C 21 H 19 NSe2[M+1] + :446.0031;found:446.0027.

[0067] Example 2

[0068] Example 2 provides a preparation method of a diselenide compound, the structural formula and preparation method of which are as follows:

[0069]

[0070] 0.2 mmol of tetrahydroquinoline, 0.8 mmol of bis(4-methylphenyl) diselenide, 8 mg of copper chloride, 0.2 mmol of sodium iodide, and 2 ml of pyridine were added to a 50 mL Schlenk tube equipped with a magnetic stirrer. Under a 1 atm oxygen atmosphere (using an oxygen balloon), the Schlenk tube was closed and heated at 50°C for 10 hours. After cooling to room temperature, the reaction mixture was filtered. Water (10 mL) and ethyl acetate (30 mL) were added to the resulting layered solution, and the aqueous layer was extracted with ethyl acetate (2 x 10 mL). The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated in vacuo. The desired product was then isolated and purified by column chromatography using silica gel as the stationary phase and a mixed solvent of petroleum ether and ethyl acetate (petroleum ether:ethyl acetate = 8:1, v / v) as the eluent. The yield of the desired product was 65%.

[0071] The hydrogen and carbon spectra of the obtained products are shown as follows: Figure 3 and Figure 4 The structural characterization data are as follows:

[0072] 1 H NMR(400MHz,Chloroform-d)δ7.70(d,J=1.9Hz,1H),7.27(dd,J=8.7,3.2Hz,3H),7.17(d,J=8.1Hz,2 H),7.05(d,J=8.0Hz,4H),3.37–3.30(m,2H),2.76(t,J=6.3Hz,2H),2.32(s,6H),1.93–1.87(m,2H);

[0073] 13 C NMR (101MHz, Chloroform-d) δ146.0,142.9,137.9,135.9,130.6,130.2,130.0,129.8,129.6,127.6,122.4,113.9,112.5,42.0,27.5,21.4,21.0.

[0074] HRMS(ESI):Calcd.For C 23 H 23 NSe2[M+1] + :474.0233;found:474.0235.

[0075] Example 3

[0076] Example 3 provides a preparation method of a diselenide compound, the structural formula and preparation method of which are as follows:

[0077]

[0078] 0.2 mmol of 2,2,4-trimethyltetrahydroquinoline, 1 mmol of bis(phenyl) diselenide, 12 mg of copper bromide, 0.3 mmol of sodium persulfate, and 2 ml of N,N-dimethylformamide were added to a 50 mL Schlenk tube equipped with a magnetic stirrer. Under a 1 atm oxygen atmosphere (using an oxygen balloon), the Schlenk tube was closed and heated at 70°C for 16 h. After cooling to room temperature, the reaction mixture was filtered. Water (10 mL) and ethyl acetate (30 mL) were added to the resulting layered solution, and the aqueous layer was extracted with ethyl acetate (2 x 10 mL). The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated in vacuo. The desired product was then isolated and purified by column chromatography using silica gel as the stationary phase and a mixed solvent of petroleum ether and ethyl acetate (petroleum ether:ethyl acetate = 30:1, v / v) as the eluent. The yield of the desired product was 71%.

[0079] The hydrogen and carbon spectra of the obtained products are shown as follows: Figure 5 and Figure 6 The structural characterization data are as follows:

[0080] 1 H NMR(400MHz,Chloroform-d)δ7.78(s,1H),7.51(s,1H),7.32(d,J=8.1Hz,2H),7.28(s,1H),7.21(dt,J=14.6,7.5Hz,7H), 2.92(s,1H),1.75(d,J=7.7Hz,1H),1.42(s,1H),1.37(d,J=6.7Hz,3H),1.31(d,J=11.2Hz,1H),1.17(s,3H),1.09(s,3H);

[0081] 13 C NMR(101MHz,Chloroform-d)δ145.3,143.7,136.3,134.5,131.5,129.6,129.6,12 9.2,129.0,126.8,126.5,125.8,112.9,112.5,49.7,43.8,31.2,28.4,28.1,19.9.

[0082] HRMS(ESI):Calcd.For C 24 H 25 NSe2[M+1] + :488.0386; found:488.0382.

[0083] Example 4

[0084] Example 4 provides a preparation method of a diselenide compound, the structural formula and preparation method of which are as follows:

[0085]

[0086] 0.2 mmol of benzomorpholine, 0.4 mmol of bis(phenyl) diselenide, 10 mg of copper acetate, 0.24 mmol of ammonium iodide, and 2 ml of pyridine were added to a Schlenk tube (50 mL) equipped with a magnetic stirrer. Under an oxygen atmosphere of 1 atm (using an oxygen balloon), the Schlenk tube was closed and heated at 80°C for 16 h. After cooling to room temperature, the reaction mixture was filtered. Water (10 ml) and ethyl acetate (30 ml) were added to the resulting layered solution, and the aqueous layer was extracted with ethyl acetate (2 x 10 ml). The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated in vacuo. The target product was then isolated and purified by column chromatography. The stationary phase of the column chromatography used was silica gel, and the eluent was a mixed solvent of petroleum ether and ethyl acetate (petroleum ether:ethyl acetate = 10:1, v / v). The target product yield was 64%.

[0087] The hydrogen and carbon spectra of the obtained products are shown as follows: Figure 7 and Figure 8 The structural characterization data are as follows:

[0088] 1 H NMR(400MHz,Chloroform-d)δ7.49(d,J=1.9Hz,1H),7.37(dd,J=8.1,1.5Hz,2H),7.27–7. 23(m,5H),7.23–7.17(m,3H),7.12(d,J=1.8Hz,1H),4.23–4.20(m,2H),3.48–3.43(m,2H);

[0089] 13 C NMR (101MHz, Chloroform-d) δ143.8,137.1,136.1,133.4,131.1,130.7,129.3,129.3,129.1,126.4,126.4,124.7,115.6,113.2,64.7,40.7;

[0090] HRMS(ESI):Calcd.For C 20 H 17 NOSe2[M+1] + :447.9713; found:447.9716.

[0091] Example 5

[0092] Example 5 provides a preparation method of a diselenide compound, the structural formula and preparation method of which are as follows:

[0093]

[0094] 0.2 mmol of 2,3,4,5-tetrahydro-1H-benzo[b]azepine, 0.6 mmol of bis(phenyl) diselenide, 8 mg of copper trifluoromethanesulfonate, 0.1 mmol of potassium persulfate, and 2 mL of methanol were added to a 50 mL Schlenk tube equipped with a magnetic stirrer. Under a 1 atm oxygen atmosphere (using an oxygen balloon), the Schlenk tube was closed and heated at 60°C for 12 h. After cooling to room temperature, the reaction mixture was filtered. Water (10 mL) and ethyl acetate (30 mL) were added to the resulting layered solution, and the aqueous layer was extracted with ethyl acetate (2 x 10 mL). The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated in vacuo. The desired product was then isolated and purified by column chromatography using silica gel as the stationary phase and a mixture of petroleum ether and ethyl acetate (petroleum ether:ethyl acetate = 30:1, v / v) as the eluent. The yield of the desired product was 65%.

[0095] The hydrogen and carbon spectra of the obtained products are shown as follows: Figure 9 and Figure 10 The structural characterization data are as follows:

[0096] H NMR(400MHz,Chloroform-d)δ7.80(d,J=2.0Hz,1H),7.42(d,J=2.0Hz,1H),7.38(dd,J=7.9,1.6Hz,2H),7.28–7.2 2(m,6H),7.21(dd,J=5.3,3.0Hz,2H),2.96–2.91(m,2H),2.82–2.76(m,2H),1.78–1.72(m,2H),1.71–1.66(m,2H);

[0097] 13 C NMR(101MHz,Chloroform-d)δ152.3,142.1,139.3,134.7,133.1,131.9,130. 9,129.8,129.3,129.2,126.5,126.5,119.8,119.20,48.1,36.0,30.7,26.4.

[0098] HRMS(ESI):Calcd.For C 22 H 21 NSe2[M+1] + :460.0078;found:460.0077.

[0099] Example 6

[0100] Example 6 provides a preparation method of a diselenide compound, the structural formula and preparation method are as follows:

[0101]

[0102] 0.2 mmol N,N-dimethylaniline, 0.4 mmol bis(phenyl) diselenide, 12 mg copper acetate, 0.24 mmol iodine, and 2 ml N-methylformamide were added to a 50 mL Schlenk tube equipped with a magnetic stirrer. Under a 1 atm oxygen atmosphere (using an oxygen balloon), the Schlenk tube was closed and heated at 90°C for 16 h. After cooling to room temperature, the reaction mixture was filtered. Water (10 mL) and ethyl acetate (30 mL) were added to the resulting layered solution, and the aqueous layer was extracted with ethyl acetate (2 x 10 mL). The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated in vacuo. The desired product was then isolated and purified by column chromatography using silica gel as the stationary phase and a mixed solvent of petroleum ether and ethyl acetate (petroleum ether:ethyl acetate = 5:1, v / v) as the eluent. The yield of the desired product was 60%.

[0103] The hydrogen and carbon spectra of the obtained products are shown as follows: Figure 11 and Figure 12 The structural characterization data are as follows:

[0104] 1 H NMR (400MHz, Chloroform-d) δ7.55(d,J=7.5Hz,3H),7.35–7.29(m,3H),7.24(d,J=15.8Hz,4H),7.13(t,J=7.1Hz,2H),6.75(s,1H),3.31(s,6H);

[0105] 13 C NMR (126MHz, Chloroform-d) δ160.2,159.3,155.1,138.3,137.5,135.5,132.0,130.4,125.0,124.0,121.0,115.3,114.8,110.8,55.2.

[0106] HRMS(ESI):Calcd.For C 20 H 19 NSe2[M+1] + :433.9926; found:433.9928.

[0107] Application Examples

[0108] The prepared organic selenium compound was prepared into a selenoquinoxalinone compound. The preparation process is as follows: a diselenide tetrahydroquinoxaline compound was reacted in the presence of copper chloride and oxygen at 100°C for 6 hours to obtain an aromatized diselenide quinoxaline compound. This was then reacted at room temperature in the presence of [bis(trifluoroacetoxy)iodo]benzene, acetonitrile, and water to produce a selenoquinoxalinone compound. The specific formula is as follows:

[0109]

[0110] According to the research results of Wang Yongxiang's research group in 2016 (European Journal of Medicinal Chemistry, Volume 117, 2016, Pages 19-32, DOI: 10.1016 / j.ejmech.2016.04.017.), it is specifically disclosed that the compound of formula A effectively and specifically blocks the mechanical allodynia and thermal hyperalgesia in rats caused by spinal nerve ligation without affecting the activity of NMDA receptors, prevents and reverses morphine analgesia, and relieves the tonic pain caused by formalin. Moreover, the drug has oral application potential and is a very good analgesic, as shown below. In contrast, the selenoquinoxalinone compound synthesized by the present invention not only has a similar structure, but also introduces selenium on the original basis, which may be helpful to improve its biological activity, and then has a more significant effect on analgesia. The organic selenium compounds obtained in other embodiments can be prepared into other compounds with reference to the same conditions or similar conditions, or with reference to other prior arts, and then applied to the synthesis of drugs such as analgesia, antibacterial, and antitumor.

[0111]

[0112] In addition, there are many technologies (such as Zhenda Tan, Yantang Liang, Jian Yang, Liang Cao, Huanfeng Jiang, and Min Zhang; Org. Lett. 2018, 20, 20, 6554–6558. or Zhixia Jing, Jianxi Du, Chengtao Wang, Keyume Ablajan, Tetrahedron, Volume 156, 2024, 133941, ISSN 0040-4020. etc.) that record that organic selenium compounds with similar structures have good biological activity and application value in the pharmaceutical field. Therefore, it can be inferred that the structural compounds of the present invention also have potential biological activity and application value in the pharmaceutical field.

[0113] The above is a detailed description of the embodiments of the present invention, but the present invention is not limited to the above embodiments. Various changes can be made within the knowledge of ordinary technicians in the relevant technical field without departing from the scope of the present invention.

Claims

1. A method for preparing a bis-selenium aromatic amine compound, characterized in that: The steps include: The compound of formula I, the compound of formula II, a copper catalyst, an oxidant and a solvent are mixed and reacted to obtain a compound of formula III; Wherein, the structural formulas of the compound of formula I, the compound of formula II and the compound of formula III are as follows: Wherein, R1 is selected from H, C 1～12 One of the alkyl, aromatic or heteroaromatic groups; X=C or O; R2 is selected from C 1～12 Alkyl, C 1～12 Alkoxy, phenyl or C 1～6 an alkyl-substituted phenyl group; R3 is selected from H or C 1～12 of alkyl.

2. The preparation method according to claim 1, characterized in that R1 is one or more substituents; independently selected from H, C 1～6 of alkyl.

3. The preparation method according to claim 1, characterized in that R2 is selected from C 1～6 Alkyl, C 1～6 Alkoxy, phenyl or C 1～6 an alkyl-substituted phenyl group.

4. The preparation method according to claim 1, characterized in that C 5～8 The heterocyclic group includes a heterocyclic group doped with at least one of N and O.

5. The preparation method according to claim 1, characterized in that The oxidant includes at least one of iodine, iodized salt, persulfate or hydrogen peroxide.

6. The preparation method according to claim 1, characterized in that The copper catalyst includes at least one of cupric chloride, cuprous chloride, cupric oxide, cuprous iodide, cupric bromide, copper acetate, copper sulfate, copper trifluoromethanesulfonate, and a nitrogen-doped carbon-supported copper catalyst.

7. The preparation method according to claim 1, characterized in that The reaction temperature is 25-80°C.

8. The preparation method according to claim 1, characterized in that The molar ratio of the compound of formula I to the compound of formula II is 1:(1-5).

9. The preparation method according to claim 1, characterized in that The molar ratio of the copper catalyst to the compound of formula I is (0.02-0.08):

1.

10. Use of the bis-selenium aromatic amine compound prepared by the preparation method according to any one of claims 1 to 9 in the preparation of analgesic, antibacterial and antitumor drugs.

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