A method for synthesizing a pyrrol-2-one compound

Abstract

The application belongs to the technical field of organic synthesis, and discloses a synthesis method of a pyrrol-2-one compound. The method is as follows: in the presence of an organic solvent as a reaction medium, propargyl ester and isonitrile are reacted under the action of a weak alkaline salt and a catalyst to obtain the pyrrol-2-one compound. The method has the advantages of mild reaction conditions, good functional group compatibility, high yield and simple operation, and can construct the target product in one step.

Description

Technical Field

[0001] This invention belongs to the field of organic synthesis, specifically relating to a method for synthesizing pyrrole-2-one compounds. Background Technology

[0002] Substituted 5-alkyl-1,5-dihydro-pyrrole-2-one compounds are well-known herbicides. Currently, the main synthetic methods for pyrrole-2-one compounds and their derivatives include: (1) oxidizing the methylene group ortho to the amino group of a five-membered ring to a carbonyl group. This method requires the synthesis of a five-membered ring amino compound first, and at least two steps are required: first oxidizing the methylene group to an alcohol, and then oxidizing the alcohol to a carbonyl group to construct an amide (Ye Wang, Hiroaki Kobayashi, Kazuya Yamaguchi and Noritaka Mizuno, Manganese oxide-catalyzed transformation of primary amines to primary amides through the sequence of oxidative dehydrogenation and successive, Chem. Commun., 2012, 48, 2642-2644); (2) condensation of an amino group and an intramolecular carboxyl group. This method requires the synthesis of an amino compound containing an intramolecular carboxyl group first (Francisco de Azambuja and Tatjana N. Parac-Vogt, Water-Tolerant and Atom Economical Amide Bond Formation by Metal-Substituted Polyoxometalate Catalysts, ACS). (Catal. 2019, 9, 10245-10252). The above methods for synthesizing pyrrole-2-one compounds involve multiple steps and limit the types of compounds that can be synthesized, thus restricting their application in fields such as pesticides. Therefore, exploring synthetic strategies that utilize inexpensive and readily available raw materials, employ mild reaction conditions, and can construct these compounds in one step remains a very meaningful research topic. Summary of the Invention

[0003] To overcome the shortcomings and deficiencies of existing technologies, the present invention aims to provide a one-step rapid method for constructing pyrrole-2-one compounds. The method of the present invention features mild reaction conditions, good functional group compatibility, high yield, and simple operation.

[0004] This invention is achieved through the following technical solution:

[0005] A method for synthesizing pyrrole-2-one compounds, comprising the following steps:

[0006] Using an organic solvent as the reaction medium, propargyl ester and isonitrile react in the presence of a weakly basic salt and a catalyst to obtain pyrrole-2-one compounds;

[0007] The structure of the propargyl ester is as follows:

[0008]

[0009] The structure of the isonitrile is as follows:

[0010] R 5 -NC;

[0011] The structure of the pyrrole-2-one compound is as follows:

[0012]

[0013] In each formula, R 1 For C1-C 12 Straight-chain or branched alkyl groups, phenyl groups, substituted phenyl groups, 2-pyridyl groups 3-Quinolinyl 3-Thienyl 5-Benzofuranyl 3,4-Methylenedioxyphenyl The substituents in the substituted phenyl group are 2-Me, 2-F, 3-F, 4-Me, 4-OMe, 4-CF3, 4-CO2Me, 4-OCF3, 4-F, 4-Cl, and 4-Br.

[0014] R 2 For methyl, phenyl; R 3 It is a primary alkyl group of C1-C6;

[0015] R 4 For C1-C 12 Straight-chain or branched alkyl, benzyl Phenyl Substituted phenyl, 2-pyridyl 3-Pyridyl 6-Chloro-3-pyridyl 5-Fluoro-2-pyridyl 2-Benzofuranyl 2-Furanyl group 3-Furan 2-Furfural vinyl 2-Thiophenevinyl vinyl cyclopentenyl 1,1-Dimethylpropenyl 2-Quinolinyl 2-Quinoxolinyl 4-pyridazinyl Non-carboxylic acid fragments of drug molecules or natural products; the non-carboxylic acid fragments of said drug molecules or natural products: probenecid. Fenbufen Febuxostat Osapchin Isosorbide Atalhalen Oleic acid Cinnamon acid Sorbic acid Boc-beta-alanine The substituents in the substituted phenyl group are 2-F, 3-Me, 4-Me, 4-OMe, 4-CF3, 4-CN, 4-F, 4-Cl, and 4-Br.

[0016] R 5 For tert-butyl 1,1,3,3-Tetramethylbutyl 2,6-Dimethylphenyl benzyl Cyclohexyl

[0017] R 6 For C1-C 12 Straight-chain or branched alkyl, phenyl; R 7 It is a C1-C6 straight-chain or branched alkyl, benzyl, or phenyl group.

[0018] When the pyrrole-2-one compound has the structure of formula 5, R 5 It is tert-butyl or 1,1,3,3-tetramethylbutyl.

[0019] The organic solvent is one or more of toluene, tetrahydrofuran, 1,4-dioxane, dimethyl sulfoxide, N-methylpyrrolidone, N,N-dimethylformamide, and N,N-dimethylacetamide; preferably one or more of N,N-dimethylacetamide and dimethyl sulfoxide.

[0020] The weakly basic salt is one or more of potassium formate, sodium formate, potassium carbonate, sodium carbonate, cesium carbonate, rubidium carbonate, potassium phosphate, sodium phosphate, lithium phosphate, trisodium phosphate dodecahydrate, potassium acetate, sodium acetate, cesium acetate, cesium fluoride, sodium ethoxide, sodium methoxide, sodium tert-butoxide, and sodium pentovaperate; preferably, one or more of sodium formate, potassium acetate, and sodium acetate.

[0021] The catalyst is one or more of the following: bis-(1,5-cyclooctadiene)nickel, nickel chloride, nickel chloride hexahydrate, nickel bromide, nickel iodide, bis(triphenylphosphine)nickel chloride, bis(triphenylphosphine)nickel bromide, palladium chloride, palladium bromide, palladium iodide, palladium acetate, palladium trifluoroacetate, tris(dibenzylacetone)dipalladium, tetra(triphenylphosphine)palladium, bis(triphenylphosphine)palladium dichloride, [1,1'-bis(diphenylphosphine)ferrocene]palladium dichloride, dipolyrhodium acetate, rhodium triiodide, and triphenylphosphine rhodium chloride; preferably one or more of palladium acetate and palladium chloride.

[0022] The reaction involves the addition of ligands, which are 2,2'-bipyridine, 4,4'-di-tert-butyl-2,2'-bipyridine, 2,2'-bipyridine-4,4'-dicarboxylic acid, α,α,α-tripyridine, 1,10-phenanthroline, triphenylphosphine, tricyclohexylphosphine, 1,1'-bis(diphenylphosphine)ferrocene, and 1,2-bis(diphenylphosphine)ethane.

[0023] When the catalyst is one of nickel di(triphenylphosphine) chloride, nickel di(triphenylphosphine) bromide, palladium dichloride of bis(triphenylphosphine) chloride, palladium dichloride of [1,1'-bis(diphenylphosphine)ferrocene], or rhodium triphenylphosphine chloride, no ligand is required. When other catalysts are used, adding ligands will improve the effect.

[0024] The reaction temperature is 60-120℃, preferably 90-110℃; the reaction time is 6-24 hours or the reaction completion can be detected by thin-layer chromatography.

[0025] The molar ratio of propargyl ester to isonitrile is 1:1 to 5.

[0026] The ratio of the catalyst to propargyl ester is (1 mol% - 10 mol%): 0.4 mmol, the ratio of the ligand to propargyl ester is (0.5 mol% - 10 mol%): 0.4 mmol, and the molar ratio of propargyl ester to the weakly basic salt is 1: (0.5-2).

[0027] After the reaction was complete, the product was extracted with saturated sodium chloride aqueous solution and ethyl acetate. The organic phase was dried with anhydrous sodium sulfate or anhydrous magnesium sulfate and removed by rotary evaporation under reduced pressure to obtain the crude product. The crude product was then separated by column chromatography using petroleum ether / ethyl acetate = 50 / 1 (volume ratio) as the eluent.

[0028] Reaction equation:

[0029]

[0030] Compared with the prior art, the present invention has the following beneficial effects and advantages:

[0031] The method of this invention has mild reaction conditions, good functional group compatibility, high yield, simple operation, and can construct the target product in one step. Attached Figure Description

[0032] Figure 1 This is the 1H NMR spectrum (1H NMR: 400MHz, CDCl3) of compound 4a;

[0033] Figure 2 This is the carbon spectrum (13C NMR: 126MHz, CDCl3) of compound 4a;

[0034] Figure 3 This is the 1H NMR spectrum (1H NMR: 400MHz, CDCl3) of compound 4b;

[0035] Figure 4 This is the 4b carbon spectrum (13C NMR: 101MHz, CDCl3) of compound;

[0036] Figure 5 This is the 4c ​​proton NMR spectrum (1H NMR: 400MHz, CDCl3) of the compound;

[0037] Figure 6 This is the 4c ​​carbon spectrum (13C NMR: 101MHz, CDCl3) of the compound;

[0038] Figure 7 This is the 4d proton NMR spectrum (1H NMR: 500MHz, CDCl3) of the compound;

[0039] Figure 8 This is the 4d carbon spectrum (13C NMR: 126MHz, CDCl3) of the compound;

[0040] Figure 9 This is the 4e proton NMR spectrum (1H NMR: 500MHz, CDCl3) of the compound;

[0041] Figure 10 This is the 4e carbon spectrum (13C NMR: 126MHz, CDCl3) of the compound;

[0042] Figure 11 This is the 1H NMR spectrum (1H NMR: 400MHz, CDCl3) of compound 5a;

[0043] Figure 12 This is the carbon spectrum (13C NMR: 126MHz, CDCl3) of compound 5a;

[0044] Figure 13 This is the 4f proton NMR spectrum (1H NMR: 500MHz, CDCl3) of the compound;

[0045] Figure 14This is the 4f carbon spectrum (13C NMR: 126MHz, CDCl3) of the compound. Detailed Implementation

[0046] The present invention will be further described in detail below with reference to the embodiments and accompanying drawings, but the implementation and protection of the present invention are not limited thereto.

[0047] Example 1

[0048] Starting with propargyl acetate 1a (2-methyl-4-phenyl-3-yn-2-acetate) (0.4 mmol) and tert-butylisocyanate 3a (0.8 mmol), palladium acetate (5 mol%), triphenylphosphine (10 mol%) and sodium formate (0.2 mmol) were added. Finally, 8 mL of N,N-dimethylacetamide was added. The mixture was heated and stirred at 100 °C for 12 hours in an oil bath. The mixture was then extracted and separated by adding saturated sodium chloride aqueous solution. The extracted organic phase was evaporated to dryness. The crude product was further purified by column chromatography (petroleum ether / ethyl acetate = 50 / 1 as eluent) to obtain compound 4a, with a yield of 88%.

[0049] The structure of compound 1a: Compound 4a:

[0050] 4a NMR data: 1 H NMR (400MHz, CDCl3) δ=7.40-7.32(m,5H),5.23-5.22(m,1H),5.18(s,1H),4.56(q,J=8.0,1H),1.83(s,3H),1.57(s,9H),1.25(d,J=8.0,3H). 13 C NMR (126MHz, CDCl3) δ = 170.0, 152.7, 136.2, 134.2, 133.2, 128.7, 128.5, 128.4, 118.6, 57.4, 54.7, 28.7, 22.2, 21.8. HRMS (ESI-quadrupole) m / z: [M+H] + Calcd.for C 18 H 24 NO 270.1852; found: 270.1850. The proton and carbon spectra of compound 4a are as follows: Figure 1 and 2 As shown.

[0051] Example 2

[0052] Starting with propargyl acetate 1b (2-methyl-4-2-pyridin-3-yne-2-acetate) (0.4 mmol) and tert-butylisocyanate 3a (0.8 mmol), palladium acetate (5 mol%), triphenylphosphine (10 mol%), and sodium formate (0.2 mmol) were added. Finally, 8 mL of N,N-dimethylacetamide was added, and the mixture was heated and stirred at 100 °C for 12 hours in an oil bath. The mixture was then extracted with saturated sodium chloride aqueous solution, and the extracted organic phase was evaporated to dryness. The crude product was further purified by column chromatography (petroleum ether / ethyl acetate = 50 / 1 as eluent) to give compound 4b in 68% yield.

[0053] The structural formula of compound 1b: The structure of compound 4b:

[0054] 4b NMR data: 1 H NMR(400MHz, CDCl3)δ8.64(dd,J=5.2,1.2Hz,1H),7.69-7.63(m,2H),7.22-7.19(m,1H),5.27(d,J =1.5Hz,1H),5.11(s,1H),4.90(q,J=4.0Hz,1H),1.92(s,3H),1.55(s,9H),1.31(d,J=8.0Hz,3H). 13 C NMR(101MHz, CDCl3)δ169.8,152.1,151.6,149.7,136.9,136.7,136.3,124.9,123.1,118.7,57.3,55.0,28.8,22.2,21.7.HRMS(ESI-quadrupole)m / z:[M+H] + Calcd.for C 17 H 23 N2O 271.1805; found:271.1802.

[0055] The proton and carbon spectra of compound 4b are as follows: Figure 3 and 4 As shown.

[0056] Example 3

[0057] Starting with propargyl acetate 1c (2-methyl-4-cyclopropyl-3-yne-2-acetate) (0.4 mmol) and tert-butylisocyanate 3a (0.8 mmol), palladium chloride (5 mol%), triphenylphosphine (10 mol%), and sodium acetate (0.4 mmol) were added. Finally, 8 mL of N,N-dimethylacetamide was added, and the mixture was stirred in an oil bath at 100 °C for 24 hours. The mixture was then extracted with saturated sodium chloride aqueous solution, and the extracted organic phase was evaporated to dryness. The crude product was further purified by column chromatography (petroleum ether / ethyl acetate = 50 / 1 as eluent) to give compound 4c, yield: 94%.

[0058] The structure of compound 1c is as follows The structure of compound 4c:

[0059] 4c NMR data: 1 H NMR (400MHz, CDCl3) δ5.17(dd,J=2.2,1.6Hz,1H),5.05(dd,J=2.1,0.9Hz,1H),3.87(q,J=6.3Hz,1H),1. 99-1.98(m,3H),1.57(s,1H),1.46(s,9H),1.39(d,J=4.0Hz,3H),0.94-0.73(m,3H),0.58-0.53(m,1H). 13 C NMR(101MHz, CDCl3)δ170.7,155.8,137.1,134.5,117.3,57.7,54.3,28.7,22.7,21.6,9.5,8.1,6.2.HRMS(ESI-quadrupole)m / z:[M+H] + Calcd.for C 15 H 24 NO 234.1852; found: 234.1851.

[0060] The proton and carbon spectra of compound 4c are as follows: Figure 5 and 6 As shown.

[0061] Example 4

[0062] Starting with propargyl ester 1d (2-methyl-4-cyclopropyl-3-yn-2-3-furan ester) (0.4 mmol) and tert-butylisocyanate 3a (0.8 mmol), palladium chloride (5 mol%), triphenylphosphine (10 mol%), and sodium formate (0.4 mmol) were added. Finally, 8 mL of N,N-dimethylacetamide was added, and the mixture was stirred in an oil bath at 100 °C for 12 hours. The mixture was then extracted with saturated sodium chloride aqueous solution, and the extracted organic phase was evaporated to dryness. The crude product was further purified by column chromatography (petroleum ether / ethyl acetate = 50 / 1 as eluent) to obtain compound 4d, yield: 91%.

[0063] The structure of compound 1d: The structure of compound 4d:

[0064] 4D NMR data: 1 H NMR (500MHz, CDCl3) δ7.26-7.23(m,5H),7.18-7.17(m,2H),6.13(s,1H),5.49(s,1H),5.29(s,1H),5.25(s,1H),1.82(s,3H),1.47(s,9H). 13 C NMR (126MHz, CDCl3) δ170.6,150.9,143.3,140.4,135.9,134.5,133.1,128.5,128.2, 128.2,124.0,119.0,108.2,58.0,55.6,28.4,22.3.HRMS(ESI-quadrupole)m / z:[M+H] + Calcd.forC 21 H 24 NO2 322.1802; found:322.1801.

[0065] The proton and carbon spectra of compound 4d are as follows: Figure 7 and 8 As shown.

[0066] Example 5

[0067] Starting with propargyl ester 1e (2-methyl-4-cyclopropyl-3-yn-2-3-furan ester) (0.4 mmol) and tert-butylisocyanate 3a (0.8 mmol), palladium chloride (5 mol%), triphenylphosphine (10 mol%), and sodium formate (0.4 mmol) were added. Finally, 8 mL of N,N-dimethylacetamide was added, and the mixture was stirred in an oil bath at 100 °C for 12 hours. The mixture was then extracted with saturated sodium chloride aqueous solution, and the extracted organic phase was evaporated to dryness. The crude product was further purified by column chromatography (petroleum ether / ethyl acetate = 50 / 1 as eluent) to give compound 4e, yield: 75%.

[0068] The structure of compound 1e: The structure of compound 4e:

[0069] 4e NMR data: 1 H NMR (500MHz, CDCl3) δ8.04(s,1H),7.92(d,J=8.9Hz,1H),7.27(d,J=4.1Hz,3H),7.16-7.15(m,2H),6.95(d,J=8.8Hz,1H),5.70(s,1H ),5.35(s,1H),5.27(s,1H),3.86(d,J=6.4Hz,2H),2.27(s,3H),2.20-2.14(m,1H),1.80(s,3H),1.49(s,9H),1.06(d,J=6.7Hz,6H). 13 C NMR (126MHz, CDCl3) δ170.2,163.6,161.9,152.0,150.4,135.3,134.4,132.8,132.1,131.5,129.0,128.4,128.1,1 26.5,119.7,115.6,112.5,102.7,75.6,59.5,55.9,28.3,28.2,22.3,19.1,15.6.HRMS(ESI-quadrupole)m / z:[M+H] + Calcd.for C 32 H 36 N3O2S

[0070] 526.2523; found: 526.2529.

[0071] The proton and carbon spectra of compound 4e are as follows: Figure 9 and 10 As shown.

[0072] Example 6

[0073] Starting with propargyl acetate 2a (3-phenyl-2-ynyl-cyclohexyl acetate) (0.4 mmol) and tert-butylisocyanate 3a (0.8 mmol), palladium chloride (5 mol%), triphenylphosphine (10 mol%), and sodium formate (0.2 mmol) were added, followed by the addition of 8 mL of N,N-dimethylacetamide. The mixture was stirred in an oil bath at 100 °C for 12 hours. Extraction with saturated sodium chloride solution was performed, and the organic phase was evaporated to dryness. The crude product was further purified by column chromatography (petroleum ether / ethyl acetate = 50 / 1 as eluent) to obtain compound 5a, yield: 73%.

[0074] The structure of compound 2a: The structure of compound 5a:

[0075] 5a NMR data: 1 H NMR (400MHz, CDCl3) δ7.38-7.32(m,5H),5.89-5.88(m,1H),4.56(q,J=8.0Hz,1H),2.22-2.18(m,1H ),2.12(d,J=4.0Hz,2H),1.87-1.82(m,1H),1.63-1.60(m,4H),1.57(s,9H),1.25(d,J=4.0Hz,3H). 13 C NMR (126MHz, CDCl3) δ170.6,151.5,134.8,133.6,129.9,129.6,128.5,128.43,128. 42,57.2,54.8,28.8,27.6,25.5,22.7,22.0,21.9.HRMS(ESI-quadrupole)m / z:[M+H] + Calcd.for C 21 H 28 NO 310.2165; found: 310.2161.

[0076] The proton and carbon spectra of compound 5a are as follows: Figure 11 and 12 As shown.

[0077] Example 7

[0078] Starting with propargyl acetate 1f (2,4-diphenyl-3-yne-2-acetate) (0.4 mmol) and tert-butylisocyanate 3a (0.8 mmol), palladium chloride (5 mol%), triphenylphosphine (10 mol%), and sodium formate (0.4 mmol) were added. Finally, 8 mL of N,N-dimethylacetamide was added, and the mixture was stirred in an oil bath at 100 °C for 12 hours. The mixture was then extracted with saturated sodium chloride aqueous solution, and the extracted organic phase was evaporated to dryness. The crude product was further purified by column chromatography (petroleum ether / ethyl acetate = 50 / 1 as eluent) to give compound 4f, yield: 67%.

[0079] The structure of propargyl acetate 1f: The structure of compound 4f:

[0080] 4F NMR data: 1 H NMR (500MHz, CDCl3) δ7.35-7.30(m,4H),7.24-7.16(m,6H),5.79(s,1H),5.38(s,1H),4.73(q,J=5.0Hz,1H),1.59(s,9H),1.37(d,J=5.0Hz,3H). 13 C NMR (126MHz, CDCl3) δ170.3,154.9,140.2,139.3,133.3,132.5,128.9,128.5,128.4, 128.4,127.7,126.4,118.4,57.6,55.0,28.9,22.5.HRMS(ESI-quadrupole)m / z:[M+H] + Calcd.forC 23 H 26 NO 332.2009; found: 332.2004.

[0081] The proton and carbon spectra of compound 4f are as follows: Figure 13 and 14 As shown.

[0082] Comparative Example 1

[0083] Starting with propargyl acetate 1a (2-methyl-4-phenyl-3-yn-2-acetate) (0.4 mmol) and tert-butylisocyanate 3a (0.8 mmol), palladium acetate (5 mol%), triphenylphosphine (10 mol%), and cesium carbonate (0.4 mmol) were added, followed by 8 mL of N,N-dimethylacetamide. The mixture was heated and stirred at 100 °C for 24 hours in an oil bath. Extraction with saturated sodium chloride solution was performed, and the organic phase was evaporated to dryness. The crude product was further purified by column chromatography (petroleum ether / ethyl acetate = 50 / 1 as eluent) to give compound 4a, yield: 25%.

[0084] The structure of compound 1a: The structure of compound 4a:

[0085] Comparative Example 2

[0086] Starting with propargyl acetate 1a (2-methyl-4-phenyl-3-yn-2-acetate) (0.4 mmol) and tert-butylisocyanate 3a (0.4 mmol), palladium acetate (5 mol%), triphenylphosphine (10 mol%), and sodium formate (0.1 mmol) were added. Finally, 8 mL of N,N-dimethylacetamide was added, and the mixture was heated and stirred at 100 °C for 24 hours in an oil bath. The mixture was then extracted with saturated sodium chloride aqueous solution, and the extracted organic phase was evaporated to dryness. The crude product was further purified by column chromatography (petroleum ether / ethyl acetate = 50 / 1 as eluent) to give compound 4a, yield: 31%.

[0087] The structure of compound 1a: The structure of compound 4a:

[0088] Comparative Example 3

[0089] Starting with propargyl acetate 1a (2-methyl-4-phenyl-3-yn-2-acetate) (0.4 mmol) and tert-butylisocyanate 3a (0.8 mmol), palladium acetate (5 mol%), triphenylphosphine (10 mol%), and sodium formate (0.2 mmol) were added. Finally, 8 mL of N,N-dimethylacetamide was added, and the mixture was heated and stirred in an oil bath at 70 °C for 24 hours. The mixture was then extracted with saturated sodium chloride aqueous solution, and the extracted organic phase was evaporated to dryness. The crude product was further purified by column chromatography (petroleum ether / ethyl acetate = 50 / 1 as eluent) to give compound 4a, yield: 23%.

[0090] The structure of compound 1a: The structure of compound 4a:

[0091] The above embodiments are preferred embodiments of the present invention, but the embodiments of the present invention are not limited to the above embodiments. Any changes, modifications, substitutions, combinations, or simplifications made without departing from the spirit and principle of the present invention shall be considered equivalent substitutions and shall be included within the protection scope of the present invention.

Claims

1. A method for synthesizing pyrrole-2-one compounds, characterized in that: Includes the following steps: Using an organic solvent as the reaction medium, propargyl ester and isonitrile react in the presence of a weakly basic salt and a catalyst to obtain pyrrole-2-one compounds; The structure of the propargyl ester is as follows: or ; The isonitrile has the structure R 5 -NC; The structure of the pyrrole-2-one compound is as follows: or ; In each formula, R 1 It is phenyl, 2-pyridyl; R 2 For methyl, phenyl; R 3 It is a primary alkyl group of C1-C6; R 4 For C1-C 12 Straight-chain or branched alkyl groups, 2-furanyl, 3-furanyl, ;R 5 For tert-butyl; R 6 It is phenyl; R 7 It is a C1-C6 straight-chain or branched alkyl group; In equations 2 and 5, n is 2; The organic solvent is one or more of N,N-dimethylacetamide and dimethyl sulfoxide; The weakly basic salt is one or more of sodium formate, potassium acetate, and sodium acetate; The catalyst is one or more of palladium acetate and palladium chloride; When the catalyst is one or more of palladium chloride and palladium acetate, a ligand is added during the reaction. The ligands are 2,2'-bipyridine, 4,4'-di-tert-butyl-2,2'-bipyridine, 2,2'-bipyridine-4,4'-dicarboxylic acid, α,α,α-tripyridine, 1,10-phenanthroline, triphenylphosphine, tricyclohexylphosphine, 1,1'-bis(diphenylphosphine)ferrocene, and 1,2-bis(diphenylphosphine)ethane; The reaction temperature is 60-120℃; the reaction time is 6-24 hours or the reaction completion can be detected by thin-layer chromatography. The molar ratio of propargyl ester to isonitrile is 1:1~5; The catalyst to propargyl ester ratio is (1 mol% - 10 mol%): 0.4 mmol, and the ligand to propargyl ester ratio is (0.5 mol% - 10 mol%): 0.4 mmol, wherein the molar ratio of the propargyl ester to the weakly basic salt is 1:(0.5-2).

2. The method for synthesizing pyrrole-2-one compounds according to claim 1, characterized in that: After the reaction was complete, the product was extracted with saturated sodium chloride aqueous solution and ethyl acetate. The organic phase was dried with anhydrous sodium sulfate or anhydrous magnesium sulfate and removed by rotary evaporation under reduced pressure to obtain the crude product. Then, the product was separated by column chromatography using petroleum ether / ethyl acetate = 50 / 1 as the eluent.

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