Preparation method of heteroaryl fused quinolinone compound

Abstract

The invention discloses a preparation method of a heteroaromatic ring fused quinolinone derivative, and belongs to the technical field of synthesis, the preparation method comprises the following steps: dissolving a substrate as shown in a formula I and a photocatalyst in an organic solvent, and reacting under the condition of light irradiation to obtain the heteroaromatic ring fused quinolinone derivative as shown in a formula II, the chemical equation of the preparation method is shown in the specification. The heteroaryl fused quinolinone derivative is synthesized by taking the indole amide derivative as a raw material, new reaction conditions are provided for synthesis of a heteroaryl fused quinolinone compound, the reaction conditions are milder, and the use of an expensive metal palladium catalyst, high-energy ultraviolet rays and a high-price metal iridium compound catalyst is avoided. # imgabs0 #

Description

Technical Field

[0001] The invention relates to the technical field of organic synthesis, and in particular to a method for preparing a heteroaryl-fused quinolinone compound. Background Art

[0002] Heteroaryl-fused quinolinone compounds have a wide range of applications in drugs, materials and synthetic intermediates. For example, as drugs, they have multiple biological activities, such as anti-tumor activity against osteosarcoma and colorectal cancer, topoisomerase and DYRK1A inhibitory activity, and Tankyrase enzyme inhibitory activity; as synthetic intermediates, they can be used to synthesize other drugs or active molecules, such as synthesizing indolequinoline derivatives with multiple biological activities; as materials for the preparation of OLED devices or intermediates for the synthesis of their materials, etc. Therefore, the method for preparing heteroaryl-fused quinolinone compounds has application value.

[0003] At present, there are several methods for synthesizing such compounds: (1) intramolecular dehydrogenation cyclization catalyzed by precious metals; (2) intramolecular dehalogenation cyclization catalyzed by metals; (3) dehalogenation cyclization reaction promoted by ultraviolet light; (4) oxidative dehydrogenation cyclization promoted by ultraviolet light; (5) dehydrogenation cyclization catalyzed by metal complexes under visible light conditions. The first two methods require the use of expensive palladium metal, with an addition amount of 10%, and the reaction needs to be heated to 100°C; the third method uses chlorine-containing raw materials and is carried out under high-energy ultraviolet light conditions; the fourth method is carried out under high-energy ultraviolet light and oxygen conditions; the fifth method requires a metal iridium complex. The metal iridium catalyst is a non-renewable resource and is expensive. The raw material of iridium trichloride for preparing and synthesizing the catalyst is expensive.

[0004] The existing methods for preparing heteroaryl-fused quinolinone compounds have the disadvantages of expensive catalysts, low substrate adaptability, high energy consumption, and metal catalyst residues. Therefore, it is urgent to develop a method for preparing heteroaryl-fused quinolinone compounds with greener and milder conditions. Summary of the invention

[0005] The purpose of the present invention is to provide a new method for preparing heteroaryl-fused quinolinone compounds under greener and milder conditions, so as to solve the problems of using expensive metal catalysts (using metal catalysts has the problem of causing metal residues in the product) and high-energy ultraviolet light in the prior art.

[0006] In order to solve the above technical problems, the present invention adopts the following technical solutions:

[0007] A method for preparing a heteroaryl-fused quinolinone compound comprises the following steps: dissolving a substrate shown in formula I and a photocatalyst in an organic solvent, reacting under light conditions, and purifying and separating after the reaction to obtain a heteroaryl-fused quinolinone compound shown in formula II.

[0008] The chemical reaction equation of the preparation method is as follows:

[0009]

[0010] in,

[0011] R 1 is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, halogen or alkoxy;

[0012] R 2 is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, alkoxy, benzyloxy or halogen;

[0013] R 3 is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, allyl or benzyl;

[0014] n=0 or 1, when n=1, X is nitrogen, oxygen or sulfur; when n=0, Y is nitrogen, oxygen or sulfur;

[0015] Z is N or CH;

[0016] The photocatalyst is 2CzPN or cyanocarbazole catalyst;

[0017] The light is blue light, white light or sunlight, preferably blue light.

[0018] In some technical solutions, R 1 is hydrogen, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted cycloalkyl, halogen, methoxy, ethoxy, trifluoromethoxy, difluoromethyl, trifluoromethyl;

[0019] R 2 is hydrogen, substituted or unsubstituted C1-C6 alkyl, trifluoromethyl, difluoromethyl, alkoxy, benzyloxy or halogen;

[0020] R 3 is hydrogen, substituted or unsubstituted C1-C6 alkyl, allyl or benzyl;

[0021] n=0 or 1, when n=1, X is nitrogen, oxygen or sulfur; when n=0, Y is nitrogen, oxygen or sulfur;

[0022] Z is N or CH.

[0023] In some technical solutions, R 1 is hydrogen, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, trifluoromethoxy, benzyloxy, trifluoromethyl or chlorine;

[0024] R 2is hydrogen, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, trifluoromethyl, benzyloxy, trifluoromethyl or chlorine;

[0025] R 3 is hydrogen, methyl, ethyl, isopropyl, cyclobutyl, propenyl or benzyl;

[0026] n=0 or 1, when n=1, X is nitrogen, oxygen or sulfur; when n=0, Y is nitrogen, oxygen or sulfur;

[0027] Z is N or CH.

[0028] In some technical solutions, R 1 is hydrogen, methyl, methoxy, trifluoromethyl, fluorine, chlorine, or bromine;

[0029] R 2 is hydrogen, methyl, ethyl, isopropyl, methoxy, ethoxy, benzyloxy, trifluoromethyl, fluorine, chlorine, bromine;

[0030] R 3 is hydrogen, methyl, propenyl or benzyl;

[0031] n=0 or 1, when n=1, X is nitrogen, oxygen or sulfur; when n=0, Y is nitrogen, oxygen or sulfur;

[0032] Z is CH.

[0033] In some technical solutions, the cyanocarbazole catalyst is a cyanocarbazole catalyst of the structure shown in Formula III:

[0034]

[0035] Among them, R is methyl, ethyl, isopropyl, cyclobutyl, benzyl; preferably methyl, ethyl, cyclobutyl, benzyl; more preferably methyl and benzyl.

[0036] In some technical schemes, the ratio of the substrate, the photocatalyst and the organic solvent is 1 mmol: 0.005-0.25 mmol: 10-40 mL; preferably 1 mmol: 0.01-0.05 mmol: 20-40 mL.

[0037] In some technical solutions, the organic solvent is a mixed solvent of a halogenated hydrocarbon solvent and dimethyl sulfoxide. Preferably, the volume ratio of the halogenated hydrocarbon solvent to dimethyl sulfoxide is 9.5:0.5-0.5:9; more preferably 9:1.

[0038] In some technical schemes, the halogenated hydrocarbon solvent is at least one of dichloromethane, 1,2-dichloroethane, 1,2-dibromoethane or chloroform; preferably 1,2-dibromoethane or 1,2-dichloroethane; further preferably 1,2-dichloroethane.

[0039] In some technical schemes, the volume ratio of 1,2-dichloroethane to dimethyl sulfoxide is 9:1.

[0040] In some specific technical solutions, the preparation method of the heteroaryl-fused quinolinone compound comprises the following steps: dissolving an aryl amide derivative and a photocatalyst in an organic solvent, and reacting under light irradiation conditions to obtain a heteroaryl-fused quinolinone derivative;

[0041] Wherein, the photocatalyst is 2CzBN or a cyanocarbazole catalyst having a structure shown in formula III:

[0042]

[0043] Wherein, R is methyl, ethyl, cyclobutyl, benzyl;

[0044] The organic solvent is a mixed solvent of 1,2-dichloroethane and dimethyl sulfoxide or 1,2-dibromoethane;

[0045] The lighting condition is blue light, white light or sunlight;

[0046] The chemical structure of the arylamide derivative is any one of the following compounds:

[0047]

[0048] Preferably, the ratio of the aromatic amide derivative, the photocatalyst and the organic solvent is 1 mmol: 0.005-0.05 mmol: 10-40 mL; more preferably, it is 1 mmol: 0.01-0.05 mmol: 20-40 mL.

[0049] Preferably, the ratio of 1,2-dichloroethane to dimethyl sulfoxide in the organic solvent is 9.5:0.5 to 0.5:9; more preferably 9:1.

[0050] Preferably, the lighting condition is blue light.

[0051] The present invention has the following beneficial effects:

[0052] (1) The present invention provides new reaction conditions for the synthesis of heteroaryl-fused quinolinone compounds. The reaction conditions are milder, not only avoiding the use of high-energy ultraviolet light, but also avoiding the use of expensive metal catalysts (eliminating the possibility of metal residues in the product, which is crucial for drugs);

[0053] (2) Metal catalysts are non-renewable, and the use of the organic catalyst of the present invention is more environmentally friendly;

[0054] (3) The unit price of obtaining cyanocarbazole catalyst is lower. Taking fac-Ir(dFppy)3 (CAS No. 391665-84-2, referred to as A), 4CzBnBN (referred to as B), and 4CzMeBN (referred to as C) as examples, the specific analysis is shown in Table 1. Compared with the prior art, the cost of the present invention is lower.

[0055] Table 1 Analysis of raw material costs for preparing 1 gram of catalyst

[0056] DETAILED DESCRIPTION

[0057] The present invention is further illustrated by the following examples, which are only used to explain the present invention and are not used to limit the scope of the present invention. If no specific conditions are specified in the examples, the conditions are carried out according to conventional conditions or conditions recommended by the manufacturer. If the manufacturer of the reagents or instruments used is not specified, they are all conventional products that can be purchased commercially.

[0058] It is worth noting that the substrate (raw material) shown in formula I used in the present invention is prepared by the method reported in the public literature and its corresponding supporting information. Personnel in the art do not need to adjust the conditions of the preparation method in the literature to prepare the raw material involved in the present invention. The references are as follows: J.Org.Chem.2022,87,7955-7967; Org.Lett.2018,20,5696-5699.

[0059] The photocatalyst of the present invention is purchased or prepared by a method reported in a public literature and its corresponding supporting information (such as cyanocarbazole catalysts, refer to the preparation document Org. Lett. 2021, 23, 3146-3150). Specifically, the structure of the photocatalyst used in the present invention is shown below, and the other reagents used are all commercially available.

[0060]

[0061] "Substituted" means that one or more hydrogen atoms in the alkyl or cycloalkyl group are each independently replaced by a non-hydrogen substituent.

[0062] "Alkyl" is a hydrocarbon comprising a positive carbon atom, a secondary carbon atom or a tertiary carbon atom. For example, an alkyl group can have 1 to 10 carbon atoms (i.e., C1-C10 alkyl), 1 to 8 carbon atoms (i.e., C1-C8 alkyl) or 1 to 6 carbon atoms (i.e., C1-C6 alkyl). The example of a suitable alkyl group includes, but is not limited to, methyl (Me, -CH3), ethyl (Et), 1-propyl group (i-Pr, i-propyl group), 2-propyl group (i-Pr, i-propyl group), 1-butyl (n-Bu, n-butyl), 2-methyl-1-propyl group (i-Bu, i-butyl), 2-butyl (s-Bu, s-butyl), 2-methyl-2-propyl group (t-Bu, t-butyl), 1-pentyl (n- 2-Methyl-2-butyl, 3-methyl-2-butyl, 3-methyl-1-butyl, 2-methyl-1-butyl, 1-hexyl, 2-hexyl, 3-hexyl, 2-methyl-2-pentyl, 3-methyl-2-pentyl, 4-methyl-2-pentyl, 3-methyl-3-pentyl, 2-methyl-3-pentyl, 2,3-dimethyl-2-butyl, 3,3-dimethyl-2-butyl and octyl.

[0063] "Cycloalkyl" is a hydrocarbon of ring carbon atoms, for example, a cycloalkyl can have 1 to 10 carbon atoms (ie, C1-C10 cycloalkyl), 1 to 8 carbon atoms (ie, C1-C8 cycloalkyl), or 1 to 6 carbon atoms (ie, C1-C6 cycloalkyl).

[0064] In the reaction formula of the present invention, "PC" represents a visible light catalyst, "Solvent" represents an organic solvent, "Ar" represents argon gas, and "rt" represents room temperature.

[0065] The full names of some English abbreviations in the present invention are shown in Table 2.

[0066] Table 2

[0067] abbreviation Full name DCE 1,2-Dichloroethane DMSO Dimethyl sulfoxide EA Ethyl acetate DCM Dichloromethane MeOH Methanol EDB 1,2-Dibromoethane THF Tetrahydrofuran MeCN Acetonitrile 1,4-Dioxane 1,4-Dioxane

[0068] Embodiment 1:

[0069]

[0070] Add substrate 1a (0.22 mmol) and 4CzBnBN (2 mol%) to a 10 mL dry Schlenk tube equipped with a stirrer. Connect the reaction tube to a double row, evacuate and introduce argon for 3 cycles, and then add ultra-dry solvent DCE:DMSO (9:1) (8 mL) under argon atmosphere. After the reaction tube is frozen with liquid nitrogen, replaced with argon for 3 times, and thawed for 3 cycles, the reaction tube is placed in a reactor and irradiated with 30 W blue light for 11 hours. After the reaction is completed, the reaction solution is diluted with EA, washed twice with saturated brine, and the organic phase is evaporated under reduced pressure to obtain a crude product. The crude product is separated by wet loading on a 100-200 mesh silica gel column (eluent: DCM / MeOH=100 / 1) to obtain 40.6 mg of a white solid with a yield of 87%.

[0071] 1 H NMR (400MHz, DMSO) δ12.37(s,1H),11.89(s,1H),8.51-8.42(m,2H),7.67(d,J=8.3Hz,1H),7.54(d ,J=8.0Hz,1H),7.48(t,J=7.6Hz,1H),7.41(dd,J=11.2,4.1Hz,1H),7.33(dd,J=17.4,7.6Hz,2H).

[0072] 13 C NMR (101MHz, DMSO) δ156.24,139.35,135.45,128.11,126.41,126.15,123.48,122.83,122.75,121.17,118.74,118.55,116.61,113.56.

[0073] Embodiment 2:

[0074] The difference between this embodiment and embodiment 1 is that the amount of photocatalyst added is 1%.

[0075] Add substrate 1a (0.2 mmol) and 4CzBnBN (1 mol%) to a 10 mL dry Schlenk tube equipped with a stirrer. Connect the reaction tube to a double row and evacuate and introduce argon for 3 cycles, then add ultra-dry solvent DCE:DMSO (9:1) (8 mL) under argon atmosphere. After the reaction tube was frozen with liquid nitrogen, replaced with argon for 3 times, and thawed for 3 times, the reaction tube was placed in a reactor and irradiated with 30 W blue light for 11 hours. After the reaction was completed, the reaction solution was diluted with EA, washed twice with saturated brine, and the organic phase was evaporated under reduced pressure to obtain a crude product. The yield of the crude product was determined to be 68% by the nuclear magnetic resonance internal standard method.

[0076] Embodiment 3:

[0077] The difference between this embodiment and embodiment 1 is that the dosage of the photocatalyst is 5%.

[0078] Add substrate 1a (0.2 mmol) and 4CzBnBN (5 mol%) to a 10 mL dry Schlenk tube equipped with a stirrer. Connect the reaction tube to a double row and evacuate and introduce argon for 3 cycles, then add ultra-dry solvent DCE:DMSO (9:1) (8 mL) under argon atmosphere. After the reaction tube was frozen with liquid nitrogen, replaced with argon for 3 times, and thawed for 3 times, the reaction tube was placed in a reactor and irradiated with 30 W blue light for 11 hours. After the reaction was completed, the reaction solution was diluted with EA, washed twice with saturated brine, and the organic phase was evaporated under reduced pressure to obtain a crude product. The yield of the crude product was determined to be 83% by the nuclear magnetic resonance internal standard method.

[0079] Embodiment 4:

[0080] The only difference between this embodiment and Embodiment 1 is that the photocatalyst is 4CzMeBN.

[0081] Add substrate 1a (0.2 mmol) and 4CzMeBN (2 mol%) to a 10 mL dry Schlenk tube equipped with a stirrer. Connect the reaction tube to a double row and evacuate and introduce argon for 3 cycles, then add ultra-dry solvent DCE:DMSO (9:1) (8 mL) under argon atmosphere. After the reaction tube was frozen with liquid nitrogen, replaced with argon for 3 times, and thawed for 3 times, the reaction tube was placed in a reactor and irradiated with 30 W blue light for 11 hours. After the reaction was completed, the reaction solution was diluted with EA, washed twice with saturated brine, and the organic phase was evaporated under reduced pressure to obtain a crude product. The yield of the crude product was determined to be 92% by the nuclear magnetic resonance internal standard method.

[0082] Embodiment 5:

[0083] The only difference between this embodiment and embodiment 1 is that the catalyst is 2CzPN.

[0084] Add substrate 1a (0.2 mmol) and 2CzPN (2 mol%) to a 10 mL dry Schlenk tube equipped with a stirrer. Connect the reaction tube to a double row and evacuate and introduce argon for 3 cycles, then add ultra-dry solvent DCE:DMSO (9:1) (8 mL) under argon atmosphere. After the reaction tube was frozen with liquid nitrogen, replaced with argon for 3 times, and thawed for 3 times, the reaction tube was placed in a reactor and irradiated with 30 W blue light for 11 hours. After the reaction was completed, the reaction solution was diluted with EA, washed twice with saturated brine, and the organic phase was evaporated under reduced pressure to obtain a crude product. The yield of the crude product was determined to be 40% by the nuclear magnetic resonance internal standard method.

[0085] Embodiment 6:

[0086] The only difference between this embodiment and embodiment 1 is that the organic solvent is 1,2-dibromoethane (EDB).

[0087] Substrate 1a (0.2 mmol) and 4CzBnBN (2 mol%) were added to a 10 mL dry Schlenk tube equipped with a stirrer. The reaction tube was connected to a double row, and it was evacuated and passed through argon for 3 times, and then ultra-dry solvent EDB (8 mL) was added under argon atmosphere. After the reaction tube was subjected to liquid nitrogen freezing-argon replacement 3 times-thaw cycle 3 times, the reaction tube was placed in a reactor and irradiated with 30W 460nm30 W blue light for 11 hours. After the reaction was completed, the reaction solution was diluted with EA, washed twice with saturated brine, and the organic phase was evaporated under reduced pressure to obtain a crude product. The yield was determined to be 70% by the internal standard method of nuclear magnetic resonance.

[0088] Comparative Example

[0089] As shown in Table 3, the effects of different reaction conditions on product yield were investigated.

[0090] Steps:

[0091] Substrate 1a (0.1 mmol) and photocatalyst (2 mol%) were added to a 10 mL dry Schlenk tube equipped with a stirrer. The reaction tube was connected to a double row, and it was evacuated and passed through argon for 3 times, and then an ultra-dry solvent was added under an argon atmosphere. After the reaction tube was frozen with liquid nitrogen, replaced with argon for 3 times, and thawed for 3 times, the reaction tube was placed in a reactor and irradiated with 30 W blue light for reaction. After the reaction was completed, the reaction solution was diluted with EA, washed twice with saturated brine, and the organic phase was evaporated under reduced pressure to obtain a crude product. The reaction yield of product 2a was determined by the internal standard method of nuclear magnetic resonance.

[0092] Table 3 Yield data of different reaction conditions

[0093]

[0094]

[0095] Embodiment 7:

[0096]

[0097] Add substrate 1b (0.2 mmol) and photocatalyst (2 mol%) to a 10 mL dry Schlenk tube equipped with a stirrer. Connect the reaction tube to a double row and evacuate and introduce argon for 3 cycles, then add ultra-dry solvent DCE:DMSO (9:1) (8 mL) under argon atmosphere. After the reaction tube is frozen with liquid nitrogen, replaced with argon for 3 times, and thawed for 3 cycles, place the reaction tube in a reactor and irradiate with 30 W blue light for 11 hours. After the reaction is completed, dilute the reaction solution with EA, wash twice with saturated brine, and evaporate the organic phase under reduced pressure to obtain a crude product. The crude product is separated by wet loading on a 100-200 mesh silica gel column (eluent: DCM / MeOH=100 / 1) to obtain 34.7 mg of a white solid with a yield of 69%.

[0098] Results: The product was a white solid with a yield of 69%;

[0099] 1 H NMR (400MHz, DMSO) δ11.91(s,1H),8.54(d,J=8.1Hz,1H),8.47(d,J=7.7Hz,1H),7.77(d,J =8.4Hz,1H),7.57(t,J=7.7Hz,1H),7.51(d,J=8.0Hz,1H),7.44-7.28(m,3H),4.34(s,3H).

[0100] 13 C NMR (101MHz, DMSO) δ156.88,140.58,135.41,126.57,126.42,123.43,123.00,122.86,121.70,121.56,119.13,118.30,116.30,111.60,31.75.

[0101] Embodiment 8:

[0102]

[0103] A 10 mL Schlenk tube equipped with a stirrer was dried in an oven, and 0.2 mmol of the substrate indolecarboxamide substrate 1c and 0.004 mmol of the photocatalyst 4CzBnPN were loaded. Then, the Schlenk tube was connected to a vacuum line, evacuated and backfilled with argon for 3 times, and then 2 mL of a mixed solvent of 1,2-dichloroethane and dimethyl sulfoxide (volume ratio 9:1) bubbled with argon for 5 min was added under an argon flow. Finally, the sealed tube was placed at a distance of 2 cm from a 30 W blue LED (wavelength 460 nm) and stirred at room temperature for 11 h. After the reaction was completed, the solvent was removed under reduced pressure, and the heteroaryl-fused indole compound 2c was obtained by purification by silica gel column chromatography.

[0104] Results: The product was a green solid with a yield of 59%;

[0105] 1 H NMR (400MHz, DMSO) δ12.27(s,1H),8.91(dd,J=6.1,3.0Hz,1H),8.76(d,J=8.2Hz,1H),8.26( dd,J=5.8,3.2Hz,1H),7.68(dd,J=6.1,3.1Hz,2H),7.63-7.53(m,2H),7.41(t,J=7.1Hz,1H).

[0106] 13 C NMR (101MHz, DMSO) δ158.37,141.77,138.08,136.43,135.95,132.69,129.35,127.96,126.41,126.27,124.63,124.07,123.23,117.87,117.20.

[0107] Embodiment 9:

[0108]

[0109] A 10 mL Schlenk tube equipped with a stirrer was dried in an oven, and 0.2 mmol of the substrate indolecarboxamide substrate 1d and 0.004 mmol of the photocatalyst 4CzBnPN were loaded. Then, the Schlenk tube was connected to a vacuum line, evacuated and backfilled with argon for 3 times, and then 2 mL of a mixed solvent of organic solvent 1,2-dichloroethane and dimethyl sulfoxide (volume ratio 9:1) bubbled with argon for 5 min was added under an argon flow. Finally, the sealed tube was placed at a distance of 2 cm from a 30 W blue LED and stirred at room temperature for 11 h. After the reaction was completed, the solvent was removed under reduced pressure, and the heteroaryl-fused indole compound 2d was obtained by purification by silica gel column chromatography.

[0110] Results: The product was a white solid 2d with a yield of 86%.

[0111] 1 H NMR (400MHz, DMSO) δ12.41(s,1H),11.93(s,1H),8.48(dd,J=11.8,8.0Hz,2H),7.68(d,J=8.2Hz,1H ),7.55(d,J=7.6Hz,1H),7.50(t,J=7.5Hz,1H),7.43(t,J=7.1Hz,1H),7.35(dd,J=17.0,8.1Hz,2H).

[0112] 13 C NMR (101MHz, DMSO) δ156.21,139.33,135.44,128.10,126.41,126.15,123.48,122.83,122.73,121.17,118.71,118.53,116.60,113.55.

[0113] The preparation of other heteroaryl-fused quinolinone compounds was carried out by referring to Example 1 to obtain the compounds shown in Table 4.

[0114] Table 4

[0115]

[0116]

[0117]

[0118]

[0119] The method of the present invention has been described through preferred embodiments, and relevant personnel can obviously modify or appropriately change and combine the methods and applications described herein within the content, spirit and scope of the present invention to implement and apply the technology of the present invention. Those skilled in the art can refer to the content of this article and appropriately improve the process parameters. It is particularly important to point out that all similar replacements and modifications are obvious to those skilled in the art, and they are all considered to be included in the present invention.

Claims

1. A method for preparing a heteroaromatic ring-fused quinolinone derivative, characterized in that: The substrate represented by Formula I and the photocatalyst are dissolved in an organic solvent, and reacted under light irradiation conditions to obtain a heteroaromatic ring-fused quinolinone derivative represented by Formula II; The chemical reaction equation of the preparation method is as follows: in, R 1 is hydrogen, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, trifluoromethoxy, benzyloxy, trifluoromethyl or halogen; R 2 is hydrogen, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, trifluoromethoxy, benzyloxy, trifluoromethyl or halogen; R 3 is hydrogen, methyl, ethyl, isopropyl, cyclobutyl, propenyl or benzyl; n=0 or 1, when n=1, X is nitrogen, oxygen or sulfur; when n=0, Y is nitrogen, oxygen or sulfur; Z is N or CH; The photocatalyst is 2CzPN or a cyanocarbazole catalyst with a structure shown in formula III: Wherein, R is methyl, ethyl, isopropyl, cyclobutyl, benzyl; The organic solvent is a mixed solvent of 1,2-dichloroethane and dimethyl sulfoxide or 1,2-dibromoethane; The lighting condition is blue light, white light or sunlight.

2. The preparation method according to claim 1, characterized in that: R 1 is hydrogen, methyl, methoxy, trifluoromethyl or halogen; and / or, R 2 is hydrogen, methyl, ethyl, isopropyl, methoxy, ethoxy, benzyloxy, trifluoromethyl or halogen; and / or, R 3 is hydrogen, methyl, propenyl or benzyl; n=0 or 1, when n=1, X is nitrogen, oxygen or sulfur; when n=0, Y is nitrogen, oxygen or sulfur; and / or, Z is CH; And / or, the lighting condition is blue light.

3. The preparation method according to claim 2, characterized in that: R 1 is hydrogen, methyl, methoxy, trifluoromethyl, fluorine, chlorine, or bromine; and / or, R 2 is hydrogen, methyl, ethyl, isopropyl, methoxy, ethoxy, benzyloxy, trifluoromethyl, fluorine, chlorine, bromine; and / or, R 3 is hydrogen, methyl, propenyl or benzyl; n=0 or 1, when n=1, X is nitrogen, oxygen or sulfur; when n=0, Y is nitrogen, oxygen or sulfur; and / or, Z is CH; And / or, the lighting condition is blue light.

4. The preparation method according to claim 1, characterized in that: The photocatalyst is 2CzBN or a cyanocarbazole catalyst with a structure shown in formula III: Among them, R is methyl, ethyl, cyclobutyl, or benzyl.

5. The preparation method according to any one of claims 1 to 4, characterized in that: The volume ratio of the 1,2-dichloroethane to dimethyl sulfoxide is 9.5:0.5-0.5:

9.

6. The preparation method according to claim 5, characterized in that: The ratio of the substrate, the photocatalyst and the organic solvent is 1 mmol: 0.005-0.05 mmol: 10-40 mL.

7. A method for preparing a heteroaromatic ring-fused quinolinone derivative, characterized in that: The aromatic amide derivative and the photocatalyst are dissolved in an organic solvent and reacted under light irradiation to obtain a heteroaryl fused quinolinone derivative; Wherein, the photocatalyst is 2CzBN or a cyanocarbazole catalyst having a structure shown in formula III: Wherein, R is methyl, ethyl, cyclobutyl, benzyl; The organic solvent is a mixed solvent of 1,2-dichloroethane and dimethyl sulfoxide or 1,2-dibromoethane; The lighting condition is blue light, white light or sunlight; The chemical structure of the arylamide derivative is any one of the following compounds:

8. The preparation method according to claim 7, characterized in that: The ratio of the aromatic amide derivative, the photocatalyst and the organic solvent is 1 mmol: 0.005-0.05 mmol: 10-40 mL; and / or, the ratio of 1,2-dichloroethane to dimethyl sulfoxide in the organic solvent is 9.5:0.5 to 0.5:9; And / or, the lighting condition is blue light.

9. The preparation method according to claim 8, characterized in that: The ratio of the aromatic amide derivative, the photocatalyst and the organic solvent is 1 mmol: 0.005-0.05 mmol: 10-40 mL; The ratio of the organic solvent 1,2-dichloroethane to dimethyl sulfoxide is 9.5:0.5 to 0.5:9; The lighting condition is blue light.

10. The preparation method according to claim 9, characterized in that: The ratio of the aromatic amide derivative, the photocatalyst and the organic solvent is 1 mmol: 0.01-0.05 mmol: 20-40 mL; The ratio of the organic solvent 1,2-dichloroethane to dimethyl sulfoxide is 9:1; The lighting condition is blue light.

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