Method and application of synthesizing tellurium-containing oxazolidinone compounds by electrochemical fixation of carbon dioxide

Abstract

The invention discloses a method and application of synthesizing tellurium-containing oxazolidinone compounds by electrochemically fixing carbon dioxide. The synthesis method comprises dissolving propargylamine or propargylamide, ditellurium compound, additive, catalyst and electrolyte in a solvent under the atmosphere of CO2 gas; using a platinum sheet as an anode and a stainless steel sheet as a cathode, stirring and reacting at a constant current of 10-20 mA and room temperature; extracting the mixture with ethyl acetate after the reaction, drying the organic layer with anhydrous sodium sulfate, filtering, decompressing and drying the solvent, and purifying the residue by silica gel column chromatography to obtain the target product. The invention also discloses the application of tellurium-containing oxazolidinone compounds in the preparation of anti-tumor active drugs. Compared with the traditional synthesis method, the controllable, green and efficient advantages of organic electrochemistry in complex molecular synthesis are utilized, and the target product is obtained by using electrons instead of redox reagents, and the electrochemical fixation of carbon dioxide is also realized, which has a green development prospect.

Description

Technical Field

[0001] The invention relates to the field of organic compound synthesis, and relates to a method for synthesizing oxazolidinone compounds, in particular to a method for synthesizing tellurium-containing oxazolidinone compounds by electrochemically fixing carbon dioxide and an application thereof. Background Art

[0002] Inorganic tellurium AS101 (Cancer Res., 2004, 64, 1853-1860; Eur. J. Chem. 2015, 6, 374-380.) has profound anti-inflammatory properties in animal models. 2,3-Di(benzoyl)naphthoquinone (J. Med. Chem., 2010, 53, 6954-6963.) has significant antioxidant activity; the use of organic tellurium compounds as 20S proteasome inhibitors can effectively inhibit β2-trypsin-like activity (Eur. J. Med. Chem., 2014, 73, 280-285.). Organic tellurium compounds can also be used as inhibitors of cysteine ​​cathepsins V and S (Bioorg. Med. Chem. Lett., 2011, 19, 2009-2014.). Oxazolidinone compounds are widely used in antibacterial drugs (Chem. Rev., 2005, 105, 529-542.), monoamine oxidase inhibitors (J. Med. Chem., 2011, 54, 8228-8232.), chiral auxiliary agents (Tetrahedron: Asymmetry, 2004, 15, 387-399.), and chemical intermediates (Acids. Chem. Rev., 2004, 104, 5823-5846.).

[0003] CO2 has become an important C1 source in organic synthesis due to its abundance, availability and sustainability, and a variety of transformation methods have been developed to construct important heterocyclic compounds. Oxazolidinone compounds can be prepared by cyclization reactions of CO2 with various N-nucleophiles such as allylamine, propylamine, and o-alkynylaniline (Org. Lett., 2022, 24, 6755-6760; Chem. Commun., 2022, 58, 6332-6335; J. Org. Chem., 2020, 85, 14109-14120). This strategy is an important improvement on the traditional method of using toxic C1 reagents (CO or phosgene). At present, a variety of strategies have been developed to convert CO2 into differently substituted oxazolidinone compounds, such as introducing functional groups such as alkyl, aryl, and trifluoromethyl into propargylamine and CO2 to synthesize differently substituted oxazolidinone skeletons, making them more valuable for utilization.

[0004] The cyclization reaction between propargylamine and CO2 is an important strategy for constructing oxazolidinone compounds. Organic tellurium compounds, especially the synthesis of tellurium heterocyclic compounds, often require harsh reaction conditions, complex reaction steps and strong reduction catalysts (ACS Catal., 2020, 10, 2707-2712; Org. Lett., 2022, 24, 2863-2867; Angew. Chem. Int. Ed., 2019, 58, 12604-12608; Org. Chem. Front., 2022, 9, 3199-3203). At present, the synthesis of tellurium-containing oxazolidinone compounds through the cyclization reaction between propargylamine and CO2 is a new technology that is innovative and challenging. Summary of the invention

[0005] The purpose of the present invention is to provide a method and application of synthesizing new tellurium-containing oxazolidinone compounds by electrochemical fixation of carbon dioxide, so as to solve the shortcomings of the prior art such as the need for additional redox agents and harsh reaction conditions. The present invention adopts organic electrochemistry and uses electrons as redox agents, which is not only low-cost, but also can obtain the target product in a controllable, green and efficient manner by adjusting the current and voltage. Tellurium compounds are inserted into oxazolidinone compounds for the first time. The new compounds have obvious anti-tumor drug activity and realize electrochemical fixation of carbon dioxide, which has a green development prospect.

[0006] The technical solution for achieving the purpose of the present invention is:

[0007] A method for synthesizing tellurium-containing oxazolidinone compounds by electrochemically fixing carbon dioxide, comprising:

[0008] Propylamine or propylamide, ditellurium compound, additive, catalyst and electrolyte are dissolved in a solvent under a CO2 gas atmosphere; a platinum sheet is used as an anode and a stainless steel (SS) sheet is used as a cathode, and a stirring reaction is carried out at a constant current of 10 to 20 mA and room temperature for 2 to 5 hours; after the reaction is completed, the mixture is extracted with ethyl acetate, the organic layer is dried with anhydrous sodium sulfate, filtered, the solvent is dried under reduced pressure, and the residue is purified by silica gel column chromatography to obtain the target product.

[0009] The general formula of the synthesis method is:

[0010]

[0011] Wherein: 1 is a propargylamine compound, 2 is a propargylamide compound; R 1 , R 2 , R 3 , R 4All are aromatic, aliphatic or alkyl; anode: platinum (Pt); cathode: stainless steel (SS).

[0012] Furthermore, the additive is potassium carbonate, cesium carbonate or triethylamine.

[0013] Furthermore, the catalyst is cupric acetate, cuprous acetate or cupric bromide.

[0014] Furthermore, the electrolyte is lithium perchlorate, tetrabutylammonium tetrafluoroborate or tetrabutylammonium hexafluorophosphate.

[0015] Furthermore, the solvent is acetonitrile, N,N-dimethylformamide or dimethyl sulfoxide.

[0016] Furthermore, the molar ratio of propargylamine or propargylamide, ditellurium compound, additive, electrolyte and catalyst is 1:1.5-2.5:1.5-2:1.5-2.5:0.1-0.3.

[0017] Preferably, the molar ratio of the propargylamine or propargylamide, the ditellurium compound, the additive, the electrolyte and the catalyst is 1:1.5:2:2:0.2.

[0018] Furthermore, while stirring the reaction, the reaction is monitored by thin layer chromatography (TLC) until the reaction is completed. TLC can quickly monitor the reaction rate. The reaction rate of each substrate is different. Too long a reaction time may lead to the generation of by-products or excessive electrode wear.

[0019] Furthermore, the column chromatography is silica gel column chromatography, and the volume ratio of the eluent petroleum ether to ethyl acetate is 20:1 to 10:1.

[0020] Furthermore, the platinum sheet is 1 cm long and 1 cm wide; the stainless steel sheet is 1 cm long and 1 cm wide.

[0021] Organic tellurium compounds have good antioxidant and antitumor activities, and their introduction into organic molecules can significantly improve the activity of these bioactive compounds. The present invention uses carbon dioxide as a C1 source to react with alkynamines and tellurides under electrochemical conditions to synthesize various tellurium-substituted oxazolidinone compounds. The reaction involves a wide range of substrates, and glycine derivatives and dopamine derivatives can participate in the reaction. The in vitro cytotoxicity of the products to human cancer cell lines was evaluated by the MTT method (MTT is 3-(4,5-Dimethylthiazol-2-y1)-2,5-diphenyltetrazolium bromide). The results showed that most compounds showed good inhibitory activity against tumor cell lines.

[0022] The invention generates a corresponding tellurium active intermediate by electrolyzing telluride to activate the carbon-carbon triple bond in the alkynamine, thereby realizing the fixation of carbon dioxide and synthesizing the corresponding tellurium-substituted new oxazolidinone compound.

[0023] Compared with traditional redox chemistry, organic electrochemistry uses electrons as redox reagents. It is not only low-cost, but also can obtain various target products in a controllable, green and efficient manner by adjusting current, voltage and other aspects, showing great synthetic advantages in the synthesis of complex molecules. DETAILED DESCRIPTION

[0024] The method for synthesizing tellurium-containing oxazolidinone compounds by electrochemically fixing carbon dioxide of the present invention is further described below in conjunction with examples, but the present invention is not limited thereto.

[0025] Embodiment 1:

[0026] Synthesis and Characterization of (E)-3-Benzyl-5-((Benzoyl)methylene)oxazolidin-2-one:

[0027] 0.3mmol of N-benzylpropyl-2-alkyn-1-amine, 0.45mmol of diphenylditellurium, 0.6mmol of cesium carbonate, 0.06mmol of copper bromide and 0.6mmol of tetrabutyl tetrafluoroborate ammonium were placed in a 10mL three-necked round-bottom flask, and then the three-necked flask was ventilated three times to fill the interior with CO2 gas. 5mL of acetonitrile was added to dissolve, a platinum sheet (1cm x 1cm) was used as an anode, a stainless steel sheet (1cm x 1cm) was used as a cathode, and the reaction was stirred at 20mA constant current and room temperature for 3h, and monitored by thin layer chromatography. After the reaction was completed, the mixture was extracted with ethyl acetate (20mL). The organic layer was dried over anhydrous sodium sulfate, filtered, the solvent was dried under reduced pressure, and the residue was purified by silica gel column chromatography to obtain the target product (E)-3-benzyl-5-((benzoyl)methylene)oxazolidin-2-one, which was a yellow solid with a yield of 80%. The structural formula is:

[0028]

[0029] The NMR and mass spectrometry data of the compound:

[0030] 1 H NMR (400MHz, Chloroform-d) δ7.52–7.48(m,2H),7.36–7.31(m,3H),7.26–7.15(m,6H),6.40–6.37(t,J=2.5Hz,1H),4.45(s,2H),4.09(d,J=2.5Hz,2H); 13 C NMR(101MHz,Chloroform-d)δ155.63,153.36,135.76,134.80,129.69,129.09,128.39,128.24,127.79,113.55,69.48,50.19,47.96.HRMS(ESI,m / z)calculated for C 17 H 15 NO2TeH + [M+H] + :396.0165; found:396.0169.

[0031] Embodiment 2:

[0032] Synthesis and Characterization of (E)-3-(4-methylbenzyl)-5-((benzoylmethylene)oxazolidin-2-one:

[0033] 0.3mmol of N-(4-methylbenzyl)prop-2-yn-1-amine, 0.45mmol of diphenylditellurium, 0.6mmol of cesium carbonate, 0.06mmol of cupric acetate and 0.6mmol of tetrabutyl tetrafluoroborate ammonium were placed in a 10mL three-necked round-bottom flask, and then the three-necked flask was ventilated three times to fill the interior with CO2 gas. 5mL of acetonitrile was added to dissolve, a platinum sheet (1cm x1cm) was used as an anode, a stainless steel sheet (1cm x 1cm) was used as a cathode, and the reaction was stirred at 20mA constant current and room temperature for 3h, and monitored by thin layer chromatography. After the reaction was completed, the mixture was extracted with ethyl acetate (20mL). The organic layer was dried over anhydrous sodium sulfate, filtered, the solvent was dried under reduced pressure, and the residue was purified by column chromatography to obtain the target product (E)-3-(4-methylbenzyl)-5-((benzoylmethylene)oxazolidin-2-one, which was yellow oily with a yield of 65%, and the structural formula was:

[0034]

[0035] The NMR and mass spectrometry data of the compound:

[0036] 1 H NMR(400MHz,Chloroform-d)δ7.55–7.46(m,2H),7.26–7.19(m,3H),7.17–7.12(m, 4H),6.41–6.36(t,J=2.6Hz,1H),4.42(s,2H),4.09(d,J=2.5Hz,2H),2.36(s,3H); 13 CNMR(101MHz,Chloroform-d)δ155.65,153.52,138.25,135.77,131.77,129.79,129 .73,128.31,127.80,113.62,69.38,50.16,47.75,21.28.HRMS(ESI,m / z)calculated forC 18 H 17 NO2TeH + [M+H] + :410.0400; found:410.0397.

[0037] Embodiment 3:

[0038] Synthesis and Characterization of (E)-3-(3-methylbenzyl)-5-((benzoyl)methylene)oxazolidin-2-one:

[0039] 0.3mmol of N-(3-methylbenzyl)prop-2-yn-1-amine, 0.45mmol of diphenylditellurium, 0.6mmol of cesium carbonate, 0.06mmol of copper acetate and 0.6mmol of tetrabutyl tetrafluoroborate ammonium were placed in a 10mL three-necked round-bottom flask, and then the three-necked flask was evacuated and ventilated three times to fill the interior with CO2 gas. 5mL of acetonitrile was added to dissolve, a platinum sheet (1cm x1cm) was used as an anode, a stainless steel sheet (1cm x 1cm) was used as a cathode, and the reaction was stirred at 20mA constant current and room temperature for 4h, and monitored by thin layer chromatography. After the reaction was completed, the mixture was extracted with ethyl acetate (20mL). The organic layer was dried over anhydrous sodium sulfate, filtered, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to obtain the target product (E)-3-(3-methylbenzyl)-5-((benzoyl)methylene)oxazolidin-2-one as a yellow oil with a yield of 77%. The structural formula is:

[0040]

[0041] The NMR and mass spectrometry data of the compound:

[0042] 1 H NMR(400MHz,Chloroform-d)δ7.53–7.49(m,2H),7.25–7.17(m,4H),7.15–7.13(m,1H),7 .07–7.03(m,2H),6.38(t,J=2.6Hz,1H),4.41(s,2H),4.10(d,J=2.6Hz,2H),2.35(s,3H). 13 C NMR(101MHz,Chloroform-d)δ155.49,153.37,140.65,138.74,135.61,134.64,129.57,129. 02,128.82,127.65,125.19,113.56,69.30,50.08,47.79,21.37.HRMS(ESI,m / z)calculated for C 18 H 17 NO2TeH + [M+H] + :410.0400; found:410.0397.

[0043] Embodiment 4:

[0044] Synthesis and Characterization of (E)-3-(2-methylbenzyl)-5-((benzoyl)methylene)oxazolidin-2-one:

[0045] 0.3mmol of N-(2-methylbenzyl)prop-2-yn-1-amine, 0.45mmol of diphenylditellurium, 0.6mmol of cesium carbonate, 0.06mmol of copper bromide and 0.6mmol of tetrabutyl tetrafluoroborate ammonium were placed in a 10mL three-necked round-bottom flask, and then the three-necked flask was evacuated and ventilated three times to fill the interior with CO2 gas. 5mL of dimethyl sulfoxide was added to dissolve, a platinum sheet (1cm x1cm) was used as an anode, and a stainless steel sheet (1cm x 1cm) was used as a cathode. The reaction was stirred at 20mA constant current and room temperature for 4h, and monitored by thin layer chromatography. After the reaction was completed, the mixture was extracted with ethyl acetate (20mL). The organic layer was dried over anhydrous sodium sulfate, filtered, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to obtain the target product (E)-3-(2-methylbenzyl)-5-((benzoyl)methylene)oxazolidin-2-one as a yellow oil with a yield of 73%. The structural formula is:

[0046]

[0047] The NMR and mass spectrometry data of the compound:

[0048] 1 H NMR(400MHz,Chloroform-d)δ7.47–7.43(m,2H),7.19–7.16(m,2H),7.14–7.12(m,3H),7 .09–7.06(m,2H),6.31(t,J=2.6Hz,1H),4.42(s,2H),3.97(d,J=2.6Hz,2H),2.26(s,3H). 13 C NMR(101MHz,Chloroform-d)δ155.19,153.21,140.63,136.72,135.70,132.46,130.90,129. 58,128.95,127.69,126.36,113.51,69.39,50.09,45.96,19.09.HRMS(ESI,m / z)calculated for C 18 H 17 NO2TeH + [M+H] + :410.0400; found:410.0397.

[0049] Embodiment 5:

[0050] Synthesis and Characterization of (E)-3-(4-methoxybenzyl)-5-((benzoyl)methylene)oxazolidin-2-one:

[0051] 0.3mmol of N-(4-methoxybenzyl)prop-2-yn-1-amine, 0.45mmol of diphenylditellurium, 0.6mmol of cesium carbonate, 0.06mmol of copper acetate and 0.6mmol of tetrabutyl tetrafluoroborate ammonium were placed in a 10mL three-necked round-bottom flask, and then the three-necked flask was evacuated and ventilated three times to fill the interior with CO2 gas. 5mL of N,N-dimethylformamide was added to dissolve, a platinum sheet (1cm x 1cm) was used as an anode, and a stainless steel sheet (1cm x 1cm) was used as a cathode. The reaction was stirred at a constant current of 20mA and room temperature for 4h, and monitored by thin layer chromatography. After the reaction was completed, the mixture was extracted with ethyl acetate (20mL). The organic layer was dried over anhydrous sodium sulfate, filtered, the solvent was dried under reduced pressure, and the residue was purified by silica gel column chromatography to obtain the target product (E)-3-(4-methoxybenzyl)-5-((benzoyl)methylene)oxazolidin-2-one as a yellow solid with a yield of 84%. The structural formula is:

[0052]

[0053] The NMR and mass spectrometry data of the compound:

[0054] 1 H NMR(400MHz,Chloroform-d)δ7.53–7.48(m,2H),7.25–7.22(m,1H),7.21–7.16(m,4H),6.90 –6.86(m,2H),6.40–6.35(t,J=2.6Hz,1H),4.40(s,2H),4.08(d,J=2.6Hz,2H),3.81(s,3H); 13 C NMR(101MHz,Chloroform-d)δ159.71,155.60,153.53,135.79,129.74,127.81,126.85,114.48,113.61,69.38,55.44,50.09,47.45.HRMS(ESI,m / z)calculated for C 18 H 17 NO3TeH + [M+H] + :426.0349; found:426.0320.

[0055] Embodiment 6:

[0056] Synthesis and Characterization of (E)-5-((Benzoyl)methylene)-3-(4-(trifluoromethyl)benzyl)oxazolidin-2-one:

[0057] 0.3mmol of N-(4-(trifluoromethyl)benzyl)prop-2-yn-1-amine, 0.45mmol of diphenylditellurium, 0.6mmol of triethylamine, 0.06mmol of copper acetate and 0.6mmol of lithium perchlorate were placed in a 10mL three-necked round-bottom flask, and then the three-necked flask was evacuated and ventilated three times to fill the interior with CO2 gas. 5mL of N,N-dimethylformamide was added to dissolve, and a platinum sheet (1cm x 1cm) was used as an anode and a stainless steel sheet (1cm x 1cm) was used as a cathode. The reaction was stirred at a constant current of 20mA and room temperature for 4h, and monitored by thin layer chromatography. After the reaction was completed, the mixture was extracted with ethyl acetate (20mL). The organic layer was dried over anhydrous sodium sulfate, filtered, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to obtain the target product (E)-5-((benzoyl)methylene)-3-(4-(trifluoromethyl)benzyl)oxazolidin-2-one as a yellow solid with a yield of 70%. The structural formula is:

[0058]

[0059] The NMR and mass spectrometry data of the compound:

[0060] 1 H NMR (400 MHz, Chloroform-d) 1 H NMR(400MHz,Chloroform-d)δ7.64–7.61(m,2H),7.54–7.49(m,2H),7.39–7.36(m, 2H),7.25–7.16(m,3H),6.43(t,J=2.5Hz,1H),4.52(s,2H),4.10(d,J=2.5Hz,2H); 13 C NMR(101MHz,Chloroform-d)δ155.71,152.83,138.94,135.93,130.09(CF, 2 J C-F =30.42Hz),129.76,128.51,127.93,120.14(CF, 3 J C-F =3.71Hz),113.40,70.05,50.28,47.55; 19 F NMR(376MHz,Chloroform-d)δ-62.60.HRMS(ESI,m / z)calculated for C 18 H 14 F3NO2TeH + [M+H] +:464.0117; found:464.0114.

[0061] Embodiment 7:

[0062] Synthesis and Characterization of (E)-3-(4-bromobenzyl)-5-((benzoyl)methylene)oxazolidin-2-one:

[0063] 0.3mmol of N-(4-bromobenzyl)prop-2-yn-1-amine, 0.45mmol of diphenylditellurium, 0.6mmol of potassium carbonate, 0.06mmol of copper acetate and 0.6mmol of tetrabutyl hexafluorophosphate ammonium were placed in a 10mL three-necked round-bottom flask, and then the three-necked flask was evacuated and ventilated three times to fill the interior with CO2 gas. 5mL of dimethyl sulfoxide was added to dissolve, a platinum sheet (1cm x1cm) was used as an anode, and a stainless steel sheet (1cm x 1cm) was used as a cathode. The reaction was stirred at 20mA constant current and room temperature for 4h, and monitored by thin layer chromatography. After the reaction was completed, the mixture was extracted with ethyl acetate (20mL). The organic layer was dried over anhydrous sodium sulfate, filtered, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to obtain the target product (E)-3-(4-bromobenzyl)-5-((benzoyl)methylene)oxazolidin-2-one as a yellow solid with a yield of 73%. The structural formula is:

[0064]

[0065] The NMR and mass spectrometry data of the compound:

[0066] 1 H NMR(400MHz,Chloroform-d)δ7.52–7.46(m,4H),7.25–7.22(m,1H),7.20–7.17(m, 2H),7.13–7.10(m,2H),6.40(t,J=2.5Hz,1H),4.40(s,2H),4.06(d,J=2.5Hz,2H). 13 CNMR(101MHz,Chloroform-d)δ155.57,152.99,140.77,135.84,133.85,132.24,129.93,129.71,127.85,122.45,113.44,50.11,47.35.HRMS(ESI,m / z)calculated forC 17 H 14 BrNO3TeH + [M+H] + :473.9270; found:473.9288.

[0067] Embodiment 8:

[0068] Synthesis and Characterization of (E)-5-((Benzoyl)methylene)-3-(thiophen-2-ylmethyl)oxazolidin-2-one:

[0069] 0.3mmol of N-(thiophene-2-methyl)prop-2-yn-1-amine, 0.45mmol of diphenylditellurium, 0.6mmol of potassium carbonate, 0.06mmol of cuprous acetate and 0.6mmol of tetrabutylammonium hexafluorophosphate were placed in a 10mL three-necked round-bottom flask, and then the three-necked flask was evacuated and ventilated three times to fill the interior with CO2 gas. 5mL of acetonitrile was added to dissolve, a platinum sheet (1cm x1cm) was used as an anode, and a stainless steel sheet (1cm x 1cm) was used as a cathode. The reaction was stirred at 20mA constant current and room temperature for 2h, and monitored by thin layer chromatography. After the reaction was completed, the mixture was extracted with ethyl acetate (20mL). The organic layer was dried over anhydrous sodium sulfate, filtered, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to obtain the target product (E)-5-((benzoyl)methylene)-3-(thiophen-2-ylmethyl)oxazolidin-2-one as a yellow solid with a yield of 72%. The structural formula is:

[0070]

[0071] The NMR and mass spectrometry data of the compound:

[0072] 1 H NMR(400MHz,Chloroform-d)δ7.55–7.51(m,2H),7.30–7.28(m,1H),7.25–7.18(m, 3H),7.01–6.97(m,2H),6.41(t,J=2.6Hz,1H),4.65(s,2H),4.18(d,J=2.6Hz,2H). 13 CNMR(101MHz,Chloroform-d)δ155.23,153.19,136.87,135.90,129.78,127.89,127.70,127.35,126.50,113.53,69.76,50.08,42.39.HRMS(ESI,m / z)calculated forC 15 H 13 NO2 + [M+H] + :401.9807; found:401.9798.

[0073] Embodiment 9:

[0074] Synthesis and Characterization of (E)-5-((Benzoyl)methylene)-3-(furan-2-ylmethyl)oxazolidin-2-one:

[0075] 0.3mmol of N-(furan-2-methyl)prop-2-yn-1-amine, 0.45mmol of diphenylditellurium, 0.6mmol of potassium carbonate, 0.06mmol of copper bromide and 0.6mmol of lithium perchlorate were placed in a 10mL three-necked round-bottom flask, and then the three-necked flask was evacuated and ventilated three times to fill the interior with CO2 gas. 5mL of dimethyl sulfoxide solvent was added to dissolve, a platinum sheet (1cm x1cm) was used as an anode, and a stainless steel sheet (1cm x 1cm) was used as a cathode. The reaction was stirred at 20mA constant current and room temperature for 3h, and monitored by thin layer chromatography. After the reaction was completed, the mixture was extracted with ethyl acetate (20mL). The organic layer was dried over anhydrous sodium sulfate, filtered, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to obtain the target product (E)-5-((benzoyl)methylene)-3-(furan-2-ylmethyl)oxazolidin-2-one as a yellow solid with a yield of 65%. The structural formula is:

[0076]

[0077] The NMR and mass spectrometry data of the compound:

[0078] 1 H NMR(400MHz,Chloroform-d)δ7.57–7.51(m,2H),7.39–7.36(m,1H),7.26–7.18(m, 3H),6.39(t,J=2.5Hz,1H),6.35–6.29(m,2H),4.46(s,2H),4.21(d,J=2.5Hz,2H); 13 CNMR(101MHz,Chloroform-d)δ155.21,153.29,148.47,143.17,135.79,129.69,127.78,113.55,110.61,109.41,69.50,50.53,40.44.HRMS(ESI,m / z)calculated for C 15 H 13 NO3TeH + [M+H] + :386.0036; found:386.0025.

[0079] Embodiment 10:

[0080] Preparation and characterization of (E)-3-(2-(Benzo[d][1,3]dioxolan-5-yl)ethyl)-5-((phenylvinyl)methylene)oxazolidin-2-one:

[0081] 0.3mmol of N-(2-(benzo[d][1,3]dioxy-5-yl)ethyl)prop-2-yn-1-amine, 0.45mmol of diphenylditellurium, 0.6mmol of potassium carbonate, 0.06mmol of copper bromide and 0.6mmol of tetrabutylammonium hexafluorophosphate were placed in a 10mL three-necked round-bottom flask, and then the three-necked flask was evacuated and ventilated three times to fill the interior with CO2 gas. 5mL of dimethyl sulfoxide solvent was added to dissolve, and a platinum sheet (1cm x 1cm) was used as an anode and a stainless steel sheet (1cm x 1cm) was used as a cathode. The reaction was stirred at a constant current of 15mA and room temperature for 4h, and monitored by thin layer chromatography. After the reaction was completed, the mixture was extracted with ethyl acetate (20mL). The organic layer was dried over anhydrous sodium sulfate, filtered, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to obtain the target product (E)-3-(2-(benzo[d][1,3]dioxolan-5-yl)ethyl)-5-((phenylvinyl)methylene)oxazolidin-2-one as a yellow solid with a yield of 69%. The structural formula is:

[0082]

[0083] The NMR and mass spectrometry data of the compound: 1 H NMR(400MHz,Chloroform-d)δ7.56–7.49(m,2H),7.28–7.20(m,3H),6.73–6.60(m,3H),6.37(t, J=2.5Hz,1H),5.92(s,2H),4.13(d,J=2.6Hz,2H),3.50(t,J=7.3Hz,2H),2.78(t,J=7.3Hz,2H); 13 C NMR(101MHz,Chloroform-d)δ155.42,153.95,148.01,146.53,135.69,131.42,129.76,127.81, 121.64,113.66,108.98,108.61,101.08,69.04,51.30,45.40,33.57.HRMS(ESI,m / z)calculated forC 19 H 17 NO4T + [M+H] + :454.0298; found:454.0297.

[0084] Embodiment 11:

[0085] Synthesis and characterization of ethyl (E)-2-(2-oxo-5-((benzoyl)methylene)oxazolidin-3-yl)acetate:

[0086] 0.3mmol of ethyl prop-2-ene-1-glycine, 0.45mmol of diphenylditellurium, 0.6mmol of triethylamine, 0.06mmol of cuprous acetate and 0.6mmol of tetrabutyl hexafluorophosphate are placed in a 10mL three-necked round-bottom flask, and then the three-necked flask is ventilated three times to fill the interior with CO2 gas. 5mL of dimethyl sulfoxide solvent is added to dissolve, a platinum sheet (1cmx 1cm) is used as an anode, and a stainless steel sheet (1cm x 1cm) is used as a cathode. The reaction is stirred at 20mA constant current and room temperature for 5h, and monitored by thin layer chromatography. After the reaction is completed, the mixture is extracted with ethyl acetate (20mL). The organic layer is dried over anhydrous sodium sulfate, filtered, the solvent is dried under reduced pressure, and the residue is purified by silica gel column chromatography to obtain the target product (E)-2-(2-oxo-5-((benzoyl)methylene)oxazolidin-3-yl)ethyl acetate, which is yellow oily with a yield of 61%. The structural formula is:

[0087]

[0088] The NMR and mass spectrometry data of the compound:

[0089] 1 H NMR(400MHz,Chloroform-d)δ7.59–7.52(m,2H),7.29–7.19(m,3H),6.39(t,J=2.6Hz,1H),4.32(d,J= 2.6Hz,2H),4.14(q,J=7.1Hz,2H),3.59(t,J=6.5Hz,2H),2.61(t,J=6.5Hz,2H),1.25(t,J=7.1Hz,3H); 13 C NMR(151MHz,Chloroform-d)δ155.33,153.70,135.66,129.63,127.69,113.61,69.08,61.00,51.55,39.74,32.61,14.15.HRMS(ESI,m / z)calculated for C 14 H 15 NO4T + [M+H] + :392.0142; found:392.0150.

[0090] Embodiment 12:

[0091] Synthesis and Characterization of (E)-3-Benzyl-5-((p-tolyl)methylene)oxazolidin-2-one:

[0092] 0.3mmol of N-benzylpropyl-2-alkyn-1-amine, 0.45mmol of 4,4-dimethyldiphenylditellurium, 0.6mmol of cesium carbonate, 0.06mmol of copper acetate and 0.6mmol of lithium perchlorate were placed in a 10mL three-necked round-bottom flask, and then the three-necked flask was ventilated three times to fill the interior with CO2 gas. 5mL of dimethyl sulfoxide was added to dissolve, a platinum sheet (1cm x1cm) was used as an anode, a stainless steel sheet (1cm x 1cm) was used as a cathode, and the reaction was stirred at 15mA constant current and room temperature for 2h, and monitored by thin layer chromatography. After the reaction was completed, the mixture was extracted with ethyl acetate (20mL). The organic layer was dried over anhydrous sodium sulfate, filtered, the solvent was dried under reduced pressure, and the residue was purified by silica gel column chromatography to obtain the target product (E)-3-benzyl-5-((p-tolyl)methylene)oxazolidin-2-one, which was a yellow solid with a yield of 70%. The structural formula is:

[0093]

[0094] The NMR and mass spectrometry data of the compound: 1 H NMR(400MHz,Chloroform-d)δ7.42–7.38(m,2H),7.35–7.29(m,3H),7.24–7.21(m,2H),7.00–6.97(m 2H),6.33(t,J=2.6Hz,1H),4.43(s,2H),4.06(d,J=2.6Hz,2H),2.29(s,3H); 13 C NMR(101MHz,Chloroform-d)δ155.53,152.65,137.82,136.27,134.76,130.47,128. 95,128.22,128.13,109.03,69.63,50.00,47.80,21.13.HRMS(ESI,m / z)calculated for C 18 H 17 NO2TeH + [M+H] + :410.0400; found:410.0397.

[0095] Embodiment 13:

[0096] Synthesis and Characterization of (E)-3-Benzyl-5-(((4-methoxyphenyl)butynyl)methylene)oxazolidin-2-one:

[0097] 0.3mmol of N-benzylpropyl-2-yn-1-amine, 0.45mmol of 4,4-dimethoxydiphenylditellurium, 0.6mmol of cesium carbonate, 0.06mmol of cuprous acetate and 0.6mmol of tetrabutyl hexafluorophosphate ammonium were placed in a 10mL three-necked round-bottom flask, and then the three-necked flask was evacuated and ventilated three times to fill the interior with CO2 gas. 5mL of dimethyl sulfoxide was added to dissolve, and a platinum sheet (1cm x 1cm) was used as an anode and a stainless steel sheet (1cm x 1cm) was used as a cathode. The reaction was stirred at a constant current of 20mA and room temperature for 4h, and monitored by thin layer chromatography. After the reaction was completed, the mixture was extracted with ethyl acetate (20mL). The organic layer was dried over anhydrous sodium sulfate, filtered, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to obtain the target product (E)-3-benzyl-5-(((4-methoxyphenyl)butynyl)methylene)oxazolidin-2-one as a yellow solid with a yield of 66%. The structural formula is:

[0098]

[0099] The NMR and mass spectrometry data of the compound: 1 H NMR(400MHz,Chloroform-d)δ7.49–7.45(m,2H),7.36–7.29(m,3H),7.24–7.21(m,2H),6 .74–6.70(m,2H),6.30(t,J=2.6Hz,1H),4.42(s,2H),4.04(d,J=2.6Hz,2H),3.74(s,3H); 13 C NMR(101MHz,Chloroform-d)δ159.77,155.46,151.90,138.67,134.73,128.89,128. 16,128.07,115.48,101.77,70.09,55.11,49.83,47.73.HRMS(ESI,m / z)calculated for C 18 H 17 NO3TeH + [M+H] + :426.0349; found:426.0311.

[0100] Embodiment 14:

[0101] Synthesis and Characterization of (E)-3-Benzyl-5-(phenyl(benzoyl)methylene)oxazolidine-2,4-dione:

[0102] 0.3mmol of N-benzyl-3-phenylpropionamide, 0.45mmol of diphenylditellurium, 0.6mmol of potassium carbonate, 0.06mmol of copper acetate and 0.6mmol of tetrabutyl hexafluorophosphate ammonium were placed in a 10mL three-necked round-bottom flask, and then the three-necked flask was evacuated and ventilated three times to fill the interior with CO2 gas. 5mL of dimethyl sulfoxide was added to dissolve, a platinum sheet (1cm x1cm) was used as an anode, and a stainless steel sheet (1cm x 1cm) was used as a cathode. The reaction was stirred at 20mA constant current and room temperature for 2h, and monitored by thin layer chromatography. After the reaction was completed, the mixture was extracted with ethyl acetate (20mL). The organic layer was dried over anhydrous sodium sulfate, filtered, the solvent was dried under reduced pressure, and the residue was purified by silica gel column chromatography to obtain the target product (E)-3-benzyl-5-(phenyl(benzoyl)methylene)oxazolidine-2,4-dione as a yellow solid with a yield of 55%. The structural formula is:

[0103]

[0104] The NMR and mass spectrometry data of the compound: 1 H NMR(600MHz,DMSO-d6)δ7.43(d,J=8.9Hz,2H),7.39-7.38(m,3H),7.35-7.28( m,2H),7.178-7.15(m,1H),7.09-7.05(m,3H),7.03-6.97(m,4H),4.71(s,2H). 13 C NMR (151MHz, DMSO) δ161.81,151.82,140.58,140.27,135.07,134.34,132.92,128.75,128.71, 128.69,128.43,127.93,127.90,127.52,118.74,115.77,43.25.HRMS(m / z)[ESI]:calculated for C 23 H 17 NO3TeH + [M+H] + :486.0300,found486.0308.

[0105] Embodiment 15:

[0106] Synthesis and Characterization of (E)-3-(4-methoxybenzyl)-5-(phenyl(benzoyl)methylene)oxazolidine-2,4-dione:

[0107] 0.3mmol of N-(4-methoxybenzyl)-3-phenylpropionamide, 0.45mmol of diphenylditellurium, 0.6mmol of potassium carbonate, 0.06mmol of copper acetate and 0.6mmol of tetrabutylammonium hexafluorophosphate were placed in a 10mL three-necked round-bottom flask, and then the three-necked flask was evacuated and ventilated three times to fill the interior with CO2 gas. 5mL of N,N-dimethylformamide was added to dissolve, and a platinum sheet (1cm x 1cm) was used as an anode and a stainless steel sheet (1cm x 1cm) was used as a cathode. The reaction was stirred at a constant current of 20mA and room temperature for 2h, and monitored by thin layer chromatography. After the reaction was completed, the mixture was extracted with ethyl acetate (20mL). The organic layer was dried over anhydrous sodium sulfate, filtered, the solvent was dried under reduced pressure, and the residue was purified by silica gel column chromatography to obtain the target product (E)-3-(4-methoxybenzyl)-5-(phenyl(benzoyl)methylene)oxazolidine-2,4-dione as a yellow oil with a yield of 61%. The structural formula is:

[0108]

[0109] The NMR and mass spectrometry data of the compound:

[0110] 1 H NMR(400MHz,Chloroform-d)δ7.46–7.41(m,4H),7.16–7.12(m,1H),7.05–7.00(m,3H),6.98–6.92(m,4H),6.91–6.87(m,2H),4.74(s,2H),3.80(s,3H); 13 C NMR(101MHz,Chloroform-d)δ161.74,159.84,151.94,140.95,133.87,132.74,130.70,128.89,128.8 4,128.65,128.23,127.69,126.81,120.97,115.58,114.28,55.39,43.53.HRMS(ESI,m / z)calculated for C 24 H 19 NO4T + [M+H] + :516.0455; found:516.0449.

[0111] Embodiment 16:

[0112] Synthesis and Characterization of (E)-3-(4-bromobenzyl)-5-(phenyl(benzoyl)methylene)oxazolidine-2,4-dione:

[0113] 0.3mmol of N-(4-bromobenzyl)-3-phenylpropionamide, 0.45mmol of diphenylditellurium, 0.6mmol of potassium carbonate, 0.06mmol of copper acetate and 0.6mmol of tetrabutyl hexafluorophosphate ammonium were placed in a 10mL three-necked round-bottom flask, and then the three-necked flask was evacuated and ventilated three times to fill the interior with CO2 gas. 5mL of dimethyl sulfoxide was added to dissolve, a platinum sheet (1cm x1cm) was used as an anode, and a stainless steel sheet (1cm x 1cm) was used as a cathode. The reaction was stirred at 20mA constant current and room temperature for 2h, and monitored by thin layer chromatography. After the reaction was completed, the mixture was extracted with ethyl acetate (20mL). The organic layer was dried over anhydrous sodium sulfate, filtered, the solvent was dried under reduced pressure, and the residue was purified by silica gel column chromatography to obtain the target product (E)-3-(4-bromobenzyl)-5-(phenyl(benzoyl)methylene)oxazolidine-2,4-dione as a yellow oil with a yield of 53%. The structural formula is:

[0114]

[0115] The NMR and mass spectrometry data of the compound:

[0116] 1 H NMR(400MHz,Chloroform-d)δ7.53–7.48(m,2H),7.44–7.41(m,2H),7.38–7.34(m,2 H),7.17–7.12(m,1H),7.03(dd,J=5.2,1.8Hz,3H),6.98–6.91(m,4H),4.74(s,2H); 13 CNMR(101MHz,Chloroform-d)δ161.64,151.81,141.01,133.83,133.52,132.61,132.24,130.97,1 28.95,128.89,128.80,128.40,127.79,122.96,122.05,115.52,43.44.HRMS(ESI,m / z)calculated for C 23 H 16 BrNO3TeH + [M+H] + :563.9454; found:563.9430.

[0117] Embodiment 17:

[0118] Synthesis and Characterization of (E)-3-(4-methylbenzyl)-5-(phenyl(benzoyl)methylene)oxazolidine-2,4-dione:

[0119] 0.3mmol of N-(4-methylbenzyl)-3-phenylpropionamide, 0.45mmol of diphenylditellurium, 0.6mmol of potassium carbonate, 0.06mmol of copper acetate and 0.6mmol of tetrabutyl hexafluorophosphate ammonium were placed in a 10mL three-necked round-bottom flask, and then the three-necked flask was evacuated and ventilated three times to fill the interior with CO2 gas. 5mL of dimethyl sulfoxide was added to dissolve, a platinum sheet (1cm x1cm) was used as an anode, and a stainless steel sheet (1cm x 1cm) was used as a cathode. The reaction was stirred at 20mA constant current and room temperature for 2h, and monitored by thin layer chromatography. After the reaction was completed, the mixture was extracted with ethyl acetate (20mL). The organic layer was dried over anhydrous sodium sulfate, filtered, the solvent was dried under reduced pressure, and the residue was purified by silica gel column chromatography to obtain the target product (E)-3-(4-methylbenzyl)-5-(phenyl(benzoyl)methylene)oxazolidine-2,4-dione as a yellow solid with a yield of 60%. The structural formula is:

[0120]

[0121] The NMR and mass spectrometry data of the compound:

[0122] 1 H NMR (400MHz, Chloroform-d) δ7.59–7.52(m,4H),7.34–7.27(m,3H),7.18–7.14(m,3H),7.10–7.07(m,3H),4.89(s,2H),2.49(s,3H); 13 C NMR(101MHz,Chloroform-d)δ161.72,151.92,140.95,140.95,138.51,133.88,132.74,131.67,129.63,129 .18,128.88,128.84,128.65,128.23,127.69,121.00,115.59,43.79,21.29.HRMS(ESI,m / z)calculatedfor C 24 H 19 NO3TeH + [M+H] + :500.0505; found:500.0503.

[0123] Embodiment 18:

[0124] Synthesis and Characterization of (E)-3-phenylethyl-5-(phenyl(benzoyl)methylene)oxazolidine-2,4-dione:

[0125] 0.3mmol of N-phenylethyl-3-phenylpropionamide, 0.45mmol of diphenylditellurium, 0.6mmol of potassium carbonate, 0.06mmol of copper acetate and 0.6mmol of tetrabutyl hexafluorophosphate are placed in a 10mL three-necked round-bottom flask, and then the three-necked flask is ventilated three times to fill the interior with CO2 gas. 5mL of dimethyl sulfoxide is added to dissolve, a platinum sheet (1cm x1cm) is used as an anode, and a stainless steel sheet (1cm x 1cm) is used as a cathode. The reaction is stirred at 20mA constant current and room temperature for 2h, and monitored by thin layer chromatography. After the reaction is completed, the mixture is extracted with ethyl acetate (20mL). The organic layer is dried over anhydrous sodium sulfate, filtered, the solvent is dried under reduced pressure, and the residue is purified by silica gel column chromatography to obtain the target product (E)-3-phenylethyl-5-(phenyl(benzoyl)methylene)oxazolidine-2,4-dione, which is a yellow oil with a yield of 58%. The structural formula is:

[0126]

[0127] The NMR and mass spectrometry data of the compound:

[0128] 1 H NMR(600MHz,Chloroform-d)δ7.47–7.44(m,2H),7.37–7.33(m,2H),7.30–7.27(m,3H),7.1 7–7.14(m,1H),7.08–7.03(m,3H),7.00–6.95(m,4H),3.92–3.88(m,2H),3.08–3.04(m,2H); 13 C NMR(151MHz,Chloroform-d)δ161.93,151.89,140.93,137.05,133.82,132.60,128.92,128.87,128.8 6,128.85,128.67,128.27,127.70,127.07,120.97,115.56,41.56,33.78.HRMS(ESI,m / z)calculated for C 24 H 19 NO3TeH + [M+H] + :500.0505; found:500.0504.

[0129] Embodiment 19:

[0130] Synthesis and Characterization of (E)-3-Benzyl-5-(1-(phenyl)propylidene)oxazolidine-2,4-dione:

[0131] 0.3mmol of N-benzylpent-2-ynamide, 0.45mmol of diphenylditellurium, 0.6mmol of potassium carbonate, 0.06mmol of copper acetate and 0.6mmol of tetrabutyl hexafluorophosphate ammonium were placed in a 10mL three-necked round-bottom flask, and then the three-necked flask was evacuated and ventilated three times to fill the interior with CO2 gas. 5mL of dimethyl sulfoxide was added to dissolve, a platinum sheet (1cm x1cm) was used as an anode, and a stainless steel sheet (1cm x 1cm) was used as a cathode. The reaction was stirred at 20mA constant current and room temperature for 2h, and monitored by thin layer chromatography. After the reaction was completed, the mixture was extracted with ethyl acetate (20mL). The organic layer was dried over anhydrous sodium sulfate, filtered, the solvent was dried under reduced pressure, and the residue was purified by silica gel column chromatography to obtain the target product (E)-3-benzyl-5-(1-(phenyl)propylidene)oxazolidine-2,4-dione, which was a yellow oil with a yield of 40%. The structural formula is:

[0132]

[0133] The NMR and mass spectrometry data of the compound:

[0134] 1 H NMR (400MHz, Chloroform-d) δ7.96–7.90(m,2H),7.49–7.43(m,3H),7.38–7.30(m,5H),4.75(s,2H),2.38(q,J=7.4Hz,2H),0.86(t,J=7.4Hz,3H); 13 C NMR(101MHz,Chloroform-d)δ161.46,152.05,142.16,134.70,132.75,129.86,129.71,1 29.16,129.02,128.63,125.66,112.92,43.96,26.17,14.02.HRMS(ESI,m / z)calculated for C 19 H 17 NO3TeH + [M+H] + :438.0349; found:438.0350.

[0135] Embodiment 20:

[0136] Pharmacological activity study of compounds:

[0137] The in vitro inhibitory activity of the products against three cancer cell lines, MIA PaCa-2, T-24 and HepG-2, was screened by MTT method. The experimental results showed that most of the tellurium-containing oxazolidinones had good inhibitory activity against tumor cell lines. It is worth noting that the compound (E)-3-(4-methoxybenzyl)-5-(phenyl(benzoyl)methylene)oxazolidine-2,4-dione (Example 15) showed good inhibitory activity against MIA PaCa-2, T-24 and HeLa cell lines, with IC50 values ​​of 1.7±0.9, 2.8±1.0 and 4.3±0.6μM, respectively. Compound (E)-3-benzyl-5-(((4-methoxyphenyl)butynyl)methylene)oxazolidin-2-one (Example 13) has strong cytotoxicity against MIA PaCa-2, T-24 and HeLa cell lines, with IC50 values ​​of 8.4±0.7, 9.1±1.1 and 11.0±0.8 μM, respectively. In addition, compounds (E)-3-(2-(benzo[d][1,3]dioxolan-5-yl)ethyl)-5-((phenylvinyl)methylene)oxazolidin-2-one (Example 10) and (E)-3-phenylethyl-5-(phenyl(benzoyl)methylene)oxazolidin-2,4-dione (Example 18) showed good antitumor activity, with IC50 values ​​of all tumor cells below 20 μM, as shown below:

[0138]

[0139] The present invention adopts an electrochemical and copper catalyst catalyzed reaction system. In this mild catalytic system, propargyl amide or propargyl amine, CO2 and ditellurium compounds are used to synthesize various oxazolidinone compounds with moderate to excellent yields. This catalytic strategy can achieve the fixation of carbon dioxide under mild conditions. The present invention also uses this strategy to modify a series of bioactive molecules. MTT method detection shows that these products have good in vitro anti-tumor activity, indicating that the compounds synthesized by the present invention can be further used to prepare anti-tumor active drugs.

[0140] Although embodiments of the present invention have been shown and described, it will be appreciated by those skilled in the art that various changes, modifications, substitutions and variations may be made to the embodiments without departing from the principles and spirit of the present invention, and that the scope of protection of the present invention is defined by the appended claims and their equivalents.

Claims

1. A method for synthesizing tellurium-containing oxazolidinone compounds by electrochemically fixing carbon dioxide, characterized in that: include: Dissolve propargylamine or propargylamide, ditellurium compound, additive, catalyst and electrolyte in a solvent under a CO2 gas atmosphere; use a platinum sheet as an anode and a stainless steel sheet as a cathode, and stir and react for 2 to 5 hours at a constant current of 10 to 20 mA at room temperature; after the reaction is completed, extract the mixture with ethyl acetate, dry the organic layer with anhydrous sodium sulfate, filter, decompress and spin-dry the solvent, and purify the residue by column chromatography to obtain the target product; The propargylamine is The propargyl amide is The ditellurium compound is R 2 TeTeR 2 , R 1 , R 2 , R 3 , R 4 All are aromatic, aliphatic or alkyl.

2. The method for synthesizing tellurium-containing oxazolidinone compounds by electrochemically fixing carbon dioxide according to claim 1, characterized in that: The additive is potassium carbonate, cesium carbonate or triethylamine.

3. The method for synthesizing tellurium-containing oxazolidinone compounds by electrochemically fixing carbon dioxide according to claim 1, characterized in that: The catalyst is cupric acetate, cuprous acetate or cupric bromide.

4. The method for synthesizing tellurium-containing oxazolidinone compounds by electrochemically fixing carbon dioxide according to claim 1, characterized in that: The electrolyte is lithium perchlorate, tetrabutylammonium tetrafluoroborate or tetrabutylammonium hexafluorophosphate.

5. The method for synthesizing tellurium-containing oxazolidinone compounds by electrochemically fixing carbon dioxide according to claim 1, characterized in that: The solvent is acetonitrile, N,N-dimethylformamide or dimethyl sulfoxide.

6. The method for synthesizing tellurium-containing oxazolidinone compounds by electrochemically fixing carbon dioxide according to claim 1, characterized in that: The molar ratio of propargylamine or propargylamide, ditellurium compound, additive, electrolyte and catalyst is 1:1.5-2.5:1.5-2:1.5-2.5:0.1-0.

3.

7. The method for synthesizing tellurium-containing oxazolidinone compounds by electrochemically fixing carbon dioxide according to claim 1, characterized in that: The molar ratio of the propargylamine or propargylamide, the ditellurium compound, the additive, the electrolyte and the catalyst is 1:1.5:2:2:0.

2.

8. Use of the tellurium-containing oxazolidinone compound synthesized by the method according to any one of claims 1 to 7 in the preparation of anti-tumor active drugs.

9. The use according to claim 8, wherein the tellurium-containing oxazolidinone compound comprises (E)-3-(4-methoxybenzyl)-5-(phenyl(benzoyl)methylene)oxazolidine-2,4-dione, (E)-3-benzyl-5-(((4-methoxyphenyl)butynyl)methylene)oxazolidine-2-one, (E)-3-(2-(benzo[d][1,3]dioxolan-5-yl)ethyl)-5-((phenylvinyl)methylene)oxazolidine-2-one and / or (E)-3-phenylethyl-5-(phenyl(benzoyl)methylene)oxazolidine-2,4-dione.

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