A cyanoalkyl-substituted quinoline compound and a method for preparing the same

Abstract

The present application aims to provide a cyanalkyl-substituted quinoline compound and a preparation method thereof, and the structure is shown in general formula I.

Description

Technical Field

[0001] This invention relates to the field of chemistry, specifically to cyanoalkyl-substituted quinoline compounds and their preparation methods. Background Technology

[0002] Quinolines are an important type of heterocyclic compound, and many of their preparation methods were only developed in the late 19th century. Among them, polysubstituted quinolines are commonly found in some natural products, pharmaceutical intermediates, drug molecules, and functional materials. Therefore, the construction methods of polysubstituted quinolines are of great significance for the synthetic design of many active molecules.

[0003] The classic method for preparing quinoline compounds is the Povarov cyclization reaction. This method utilizes the condensation of aromatic aldehydes and aromatic amines to form a Schiff base, which then cyclizes with an electron-rich alkene or alkyne to form tetrahydroquinoline or dihydroquinoline compounds. Further dehydrogenation aromatization with an additional oxidant is then performed to synthesize quinoline compounds; DDQ (2,3-dichloro-5,6-dicyano-1,4-benzoquinone) is a common oxidant. This method typically requires the addition of an equivalent or even multiple times the amount of oxidant to achieve complete oxidation, resulting in waste of the oxidant and the excessive residue posing a certain environmental hazard. Summary of the Invention

[0004] This invention discloses a novel cyanoalkyl-substituted quinoline compound and its preparation method.

[0005] The cyanoalkyl-substituted quinoline compounds described above have the structure shown in general formula I:

[0006]

[0007] R 1 Indicates hydrogen, alkyl, alkoxy, or halogen;

[0008] R 2 It represents hydrogen, aryl, alkyl, allyl, or propyne;

[0009] R 3 It represents hydrogen, alkyl, allyl, propargyl, aryl, or benzyl;

[0010] X represents O, N, or S.

[0011] Preferred, R 1 It can represent hydrogen, alkyl groups with 1-6 carbon atoms, alkoxy groups with 1-6 carbon atoms, fluorine, chlorine, bromine, or iodine;

[0012] Preferred, R 2 Represents hydrogen, aryl, alkyl with 1-6 carbon atoms, cyclohexane, allyl, or propargyl;

[0013] Preferred, R 3 It represents hydrogen, alkyl, allyl, propargyl, aryl, or benzyl with 1-6 carbon atoms.

[0014] The compound in question is specifically:

[0015]

[0016] The reaction formula for the quinoline compounds is as follows:

[0017]

[0018] The specific reaction process is as follows: the reaction temperature is controlled at 20-35℃, and under a nitrogen-filled protective atmosphere, in an organic solvent, substituted isonitrile A and substituted cyclobutanone oxime B, in the presence of a photocatalyst and an alkaline additive, utilize visible light to induce the generation of alkyl radicals and tandem cyclization reactions with isonitriles to prepare substituted cyanoquinoline compounds of general formula I.

[0019] The organic solvent is one or a mixture of more than one of acetonitrile, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, and dichloromethane.

[0020] The reaction temperature is controlled at 22–25°C.

[0021] The catalyst is any of the following:

[0022] The complex formed by ruthenium and bipyridine has the following chemical formula:

[0023] [Ru(bpy)3]Y2, where Y = SbF6, PF6, BF4, OTf, Br, or Cl;

[0024] Iridium forms complexes with bipyridine having the following chemical formulas: fac-Ir(ppy)3, Ir(ppy)3, or [Ir(ppy)2(dtb-bpy)](PF6);

[0025] Photosensitizer: Rhodamine, or eosin Y.

[0026] The alkaline additive is one or a mixture of more than one of sodium carbonate, potassium carbonate, sodium acetate, 2,6-dimethylpyridine, or triethylenediamine.

[0027] The molar ratio of the reaction between the substituted isonitrile A and the substituted cyclobutanone oxime B is 1-5:1-5, and the catalyst is 0.5-2% of the molar amounts of the two reactants.

[0028] The visible light mentioned is 7W blue light.

[0029] The compounds of general formula I of this invention can be prepared under mild reaction conditions, and the catalysts used are inexpensive, readily available, and easy to operate. In particular, the visible light catalysis utilized represents an inexhaustible green energy source and resource from nature. Furthermore, the compounds of general formula I of this invention have wide applicability, high yield, and can well meet the synthetic design requirements of many active molecules.

[0030] The synthetic method of this invention, with "new energy utilization" and "green chemistry" as its background, utilizes a catalytic amount of commercially available metal photocatalysts or photosensitizers under visible light-induced catalysis to prepare various multi-substituted cyanoquinoline compounds under mild reaction conditions. This method uses inexpensive and readily available catalysts, is simple to operate, has mild reaction conditions, broad substrate applicability, high yield, and is more environmentally friendly. Attached Figure Description

[0031] Figure 1 This invention relates to a cyanoalkyl-substituted quinoline compound with the general structural formula I. Detailed Implementation

[0032] Example 1

[0033]

[0034] Synthesis of 4-(4-methylquinoline-2-yl)butyronitrile

[0035] Add 0.3 mmol of 1-isocyano-2-(prop-1-en-2-yl)benzene, 0.6 mmol of cyclobutanone O-(4-(trifluoromethyl)benzoyl)oxime, 6 mL of acetonitrile, 0.006 mmol of fac-Ir(ppy)3, and 0.45 mmol of sodium carbonate to a reaction tube. Place a 7W blue fluorescent lamp 5 cm away from the reaction tube, maintain the temperature at 22 °C, and stir for 24 hours under N2 protection. After the reaction is complete, concentrate the solution and directly precipitate by column chromatography to obtain the target product in 82% yield. 1 H NMR (400MHz, CDCl3) δ8.03(d,J=7.8Hz,1H),7.96(d,J=8.4Hz,1H),7.69(t,J=7.6Hz,1H),7.55–7.50(m,1H ),7.14(s,1H),3.08(t,J=7.4Hz,2H),2.69(d,J=1.0Hz,3H),2.47(t,J=7.2Hz,2H),2.23(p,J=7.2Hz,2H). 13 C NMR (101MHz, CDCl3) δ159.7,147.7,145.2,129.5,129.3,127.1,126.0,123.8,122.3,119.7,37.0,25.0,18.8,16.8.

[0036] Example 2

[0037]

[0038] Synthesis of 4-(4-isopropylquinoline-2-yl)butyronitrile

[0039] 0.3 mmol of 1-isocyano-2-(3-methylbut-1-en-2-yl)benzene, 0.6 mmol of cyclobutanone O-(4-(trifluoromethyl)benzoyl)oxime, 6 mL of dimethylformamide, 0.006 mmol of BF4, and 0.45 mmol of potassium carbonate were added to a reaction tube. A 7W blue fluorescent lamp was placed 5 cm away from the reaction tube, and the mixture was stirred for 24 hours under N2 protection at 25 °C. After the reaction was complete, the mixture was concentrated and directly subjected to column chromatography to obtain the target product in 95% yield. 1 H NMR (400MHz, CDCl3) δ8.07-8.02(m,2H),7.68(t,J=7.6Hz,1H),7.52(t,J=7.2Hz 1H),7.19(s,1H),3.76-3.69(m,1H),3.11(t,J=7.4Hz,2H),2.50(t,J=7.2Hz,2H),2.29-2.21(m,2H),1.41(d,J=6.8Hz,6H).

[0040] Example 3

[0041]

[0042] Synthesis of 4-(4-phenylquinoline-2-yl)butyronitrile

[0043] 0.3 mmol of 1-isocyano-2-(1-phenylvinyl)benzene, 0.6 mmol of cyclobutanone O-(4-(trifluoromethyl)benzoyl)oxime, 6 mL of dimethyl sulfoxide, 0.006 mmol of Ir(ppy)3, and 0.45 mmol of 2,6-dimethylpyridine were added to a reaction tube. A 6W red fluorescent lamp was placed 5 cm away from the reaction tube, and the mixture was stirred at 30 °C under N2 protection for 48 hours. After the reaction was complete, the mixture was concentrated and directly subjected to column chromatography to obtain the target product in 57% yield. 1 H NMR (400MHz, CDCl3) δ8.09(d,J=8.5Hz,1H),7.89(d,J=8.4Hz,1H),7.71(t,J=7.6Hz,1H),7.5 5-7.44(m,6H),7.24(s,1H),3.16(t,J=7.4Hz,2H),2.53(t,J=7.2Hz,2H),2.33-2.26(m,2H). 13C NMR (101MHz, CDCl3) δ159.5,149.1,148.6,138.0,129.6,129.4,128.7,128.6,126.2,125.8,125.5,121.7,119.7,37.2,24.9,16.8.

[0044] Example 4

[0045]

[0046] Synthesis of 4-(7-bromo-4-methylquinoline-2-yl)butyronitrile

[0047] 0.3 mmol of 4-bromo-2-isocyano-1-(prop-1-en-2-yl)benzene, 0.6 mmol of cyclobutanone O-(4-(trifluoromethyl)benzoyl)oxime, 6 mL of dichloromethane, 0.006 mmol of [Ru(bpy)3]Cl2, and 0.45 mmol of dimethylacetamide were added to a reaction tube. An 8W white fluorescent lamp was placed 5 cm away from the reaction tube, and the mixture was stirred for 48 hours under N2 protection at 20 °C. After the reaction was complete, the mixture was concentrated and directly subjected to column chromatography to obtain the target product in 55% yield. 1 H NMR (400MHz, CDCl3) δ8.20(d,J=2.4Hz,1H),7.82(d,J=8.8Hz,1H),7.62-7.59(m,1H),7.1 5(s,1H),3.07(t,J=7.4Hz,2H),2.67(s,3H),2.48(t,J=7.2Hz,2H),2.23(p,J=7.1Hz,2H). 13 C NMR (101MHz, CDCl3) δ160.9,148.7,145.0,131.9,129.4,125.8,125.3,123.5,122.7,119.7,36.9,24.6,18.7,16.8.

[0048] Example 5

[0049]

[0050] Synthesis of 4-(7-chloro-4-methylquinoline-2-yl)butyronitrile

[0051] 0.3 mmol of 4-chloro-2-isocyano-1-(prop-1-en-2-yl)benzene, 0.6 mmol of cyclobutanone O-(4-(trifluoromethyl)benzoyl)oxime, 6 mL of acetonitrile, 0.006 mmol of rhodamine, and 0.45 mmol of sodium acetate were added to a reaction tube. A 7W green fluorescent lamp was placed 5 cm away from the reaction tube, and the mixture was stirred for 48 hours under N2 protection at 27 °C. After the reaction was complete, the mixture was concentrated and directly subjected to column chromatography to obtain the target product in 60% yield. 1 H NMR (400MHz, CDCl3) δ8.01(s,1H),7.89(d,J=8.8Hz,1H),7.47(d,J=8.8Hz,1H),7.13 (s,1H),3.07(t,J=7.4Hz,2H),2.67(s,3H),2.48(t,J=7.2Hz,2H),2.27-2.19(m,2H).

[0052] Example 6

[0053]

[0054] Synthesis of 4-(6,7-dimethoxy-4-methylquinoline-2-yl)butyronitrile

[0055] 0.3 mmol of 1-isocyano-4,5-dimethoxy-2-(prop-1-en-2-yl)benzene, 0.6 mmol of cyclobutanone O-(4-(trifluoromethyl)benzoyl)oxime, 6 mL of dimethylformamide, 0.006 mmol of [Ir(ppy)2(dtb-bpy)](PF6), and 0.45 mmol of sodium carbonate were added to a reaction tube. A 7W white fluorescent lamp was placed 5 cm away from the reaction tube, and the mixture was stirred for 24 hours under N2 protection at 24 °C. After the reaction was complete, the mixture was concentrated and directly subjected to column chromatography to obtain the target product in 72% yield. 1 H NMR (400MHz, CDCl3) δ7.49 (s, 1H), 7.12 (s, 1H), 7.05 (s, 1H), 4.03 (d, J = 3.4Hz, 6 H),3.06(t,J=7.4Hz,2H),2.64(s,3H),2.44(t,J=7.2Hz,2H),2.24-2.16(m,2H).

[0056] Example 7

[0057]

[0058] Synthesis of 4-(4-methylquinoline-2-yl)valerate

[0059] 0.3 mmol of 1-isocyano-2-(prop-1-en-2-yl)benzene, 0.6 mmol of (E)-2-methylcyclobutane-1-one O-(4-(trifluoromethyl)benzoyl)oxime, 6 mL of dimethyl sulfoxide, 0.006 mmol of [Ru(bpy)3](BF4)2, and 0.45 mmol of triethylenediamine were added to a reaction tube. A 7W yellow fluorescent lamp was placed 5 cm away from the reaction tube, and the mixture was stirred for 48 hours under N2 protection at 31 °C. After the reaction was complete, the mixture was concentrated and directly subjected to column chromatography to obtain the target product in 57% yield. 1 H NMR (400MHz, CDCl3) δ8.03(d,J=8.4Hz,1H),7.97(d,J=8.4Hz,1H),7.69(t,J=8.0Hz,1H),7.53(t,J=6.8Hz, 1H),7.14(s,1H),3.19-3.12(m,1H),2.70(s,3H),2.37–2.26(m,3H),2.09–2.01(m,1H),1.42-1.39(m,3H).

[0060] Example 8

[0061]

[0062] Synthesis of 4-(4-methylquinolin-2-yl)hexanenitrile

[0063] 0.3 mmol of 1-isocyano-2-(prop-1-en-2-yl)benzene, 0.6 mmol of (E)-2-ethylcyclobutane-1-one O-(4-(trifluoromethyl)benzoyl)oxime, 6 mL of acetonitrile, 0.006 mmol of fac-Ir(ppy)3, and 0.45 mmol of sodium carbonate were added to a reaction tube. A 7W blue fluorescent lamp was placed 5 cm away from the reaction tube, and the mixture was stirred for 24 hours under N2 protection at 26 °C. After the reaction was complete, the mixture was concentrated and directly subjected to column chromatography to obtain the target product in 67% yield. 1 H NMR (400MHz, CDCl3) δ8.03(d,J=8.4Hz,1H),7.97(d,J=8.4Hz,1H),7.74–7.65(m,1H),7.53(t,J=7.6Hz,1H),7.11(s, 1H),2.94-2.89(m,1H),2.70(s,3H),2.30-2.18(m,3H),2.13-2.08(m,1H),1.90-1.75(m,2H),0.86(t,J=7.4Hz,3H). 13C NMR (101MHz, CDCl3) δ162.7,148.0,144.8,129.9,129.3,127.3,126.0,123.8,122.0,120.1,48.8,30.2,28.7,19.0,15.6,12.1.

[0064] Example 9

[0065]

[0066] Synthesis of 4-(4-methylquinoline-2-yl)-5-phenylpentanilide

[0067] Add 0.3 mmol of 1-isocyano-2-(prop-1-en-2-yl)benzene, 0.6 mmol of (E)-2-benzylcyclobutane-1-one O-(4-(trifluoromethyl)benzoyl)oxime, 6 mL of dichloromethane, 0.006 mmol of Ir(ppy)3, and 0.45 mmol of potassium carbonate to a reaction tube. Place a 7W blue fluorescent lamp 5 cm away from the reaction tube, maintain the temperature at 33 °C, and stir for 24 hours under N2 protection. After the reaction is complete, concentrate the solution and directly precipitate by column chromatography to obtain the target product in 84% yield. 1 H NMR (400MHz, CDCl3) δ8.06(d,J=8.4Hz,1H),7.96(d,J=8.4Hz,1H),7.70(t,J=7.6Hz,1H),7.54(t,J=7.2Hz,1H),7.25–7.10(m ,5H),7.00(s,1H),3.33-3.15(m,1H),3.20-3.15(m,1H),2.98-2.93(m,1H),2.64(s,3H),2.4–2.22(m,2H),2.18–2.02(m,2H).

[0068] Example 10

[0069]

[0070] Synthesis of 2-((4-methylquinoline-2-yl)methoxy)acetonitrile

[0071] 0.3 mmol of 1-isocyano-2-(prop-1-en-2-yl)benzene, 0.6 mmol of oxetane-3-one O-(4-(trifluoromethyl)benzoyl)oxime, 6 mL of dimethyl sulfoxide, 0.006 mmol of eosin Y, and 0.45 mmol of triethylenediamine were added to a reaction tube. A 7W blue fluorescent lamp was placed 5 cm away from the reaction tube, and the mixture was stirred for 24 hours under N2 protection at 21 °C. After the reaction was complete, the mixture was concentrated and directly subjected to column chromatography to obtain the target product in 60% yield. 1H NMR(400MHz, CDCl3)δ8.08(d,J=8.4Hz,1H),8.01(d,J=8.4Hz,1H),7.76–7.70(m,1H), 7.58(t,J=7.4Hz,1H),7.37(s,1H),4.90(s,2H),4.45(d,J=10.5Hz,2H),2.74(s,3H). 13 C NMR (101MHz, CDCl3) δ155.9,147.5,145.7,129.9,129.7,128.9,127.8,126.7,123.9,120.4,74.7,56.1,19.0.

[0072] Example 11

[0073]

[0074] Synthesis of 4-(4-methylquinoline-2-yl)-3-phenylbutyronitrile

[0075] Add 0.3 mmol of 1-isocyano-2-(prop-1-en-2-yl)benzene, 0.6 mmol of 3-phenylcyclobutane-1-one O-(4-(trifluoromethyl)benzoyl)oxime, 6 mL of acetonitrile, 0.006 mmol of fac-Ir(ppy)3, and 0.45 mmol of sodium carbonate to a reaction tube. Place a 7W blue fluorescent lamp 5 cm away from the reaction tube, maintain the temperature at 24 °C, and stir for 24 hours under N2 protection. After the reaction is complete, concentrate the solution and directly precipitate by column chromatography to obtain the target product in 62% yield. 1 H NMR (400MHz, CDCl3) δ8.04(d,J=8.4Hz,1H),7.96(d,J=8.4Hz,1H),7.70(t,J=7.6Hz,1H),7.54(t,J=7.6Hz,1 H),7.35–7.27(m,5H),7.04(s,1H),3.79–3.72(m,1H),3.36(d,J=7.6Hz,2H),2.82–2.71(m,2H),2.65(s,3H). 13 C NMR (101MHz, CDCl3) δ158.6,147.8,144.8,141.7,129.5,129.4,128.9,127.6,127.4,127.0,126.0,123.8,122.7,118.7,43.6,41.5,24.0,18.7.

[0076] Example 12

[0077]

[0078] Synthesis of 4-(4-methylquinoline-2-yl)butyronitrile

[0079] Add 0.3 mmol of 1-isocyano-2-(prop-1-en-2-yl)benzene, 0.3 mmol of cyclobutanone O-(4-(trifluoromethyl)benzoyl)oxime, 6 mL of acetonitrile, 0.006 mmol of fac-Ir(ppy)3, and 0.45 mmol of sodium carbonate to a reaction tube. Place a 7W blue fluorescent lamp 5 cm away from the reaction tube, maintain the temperature at 22 °C, and stir for 24 hours under N2 protection. After the reaction is complete, concentrate the solution and directly precipitate by column chromatography to obtain the target product.

[0080] Example 13

[0081]

[0082] Synthesis of 4-(4-isopropylquinoline-2-yl)butyronitrile

[0083] Add 0.3 mmol of 1-isocyano-2-(3-methylbut-1-en-2-yl)benzene, 1.5 mmol of cyclobutanone O-(4-(trifluoromethyl)benzoyl)oxime, 6 mL of dimethylformamide, 0.006 mmol of BF4, and 0.45 mmol of potassium carbonate to a reaction tube. Place a 7W blue fluorescent lamp 5 cm away from the reaction tube, and stir for 24 hours under N2 protection at 25 °C. After the reaction is complete, concentrate the solution and directly precipitate by column chromatography to obtain the target product.

[0084] Example 14

[0085]

[0086] Synthesis of 4-(4-phenylquinoline-2-yl)butyronitrile

[0087] Add 1.5 mmol of 1-isocyano-2-(1-phenylvinyl)benzene, 0.3 mmol of cyclobutanone O-(4-(trifluoromethyl)benzoyl)oxime, 6 mL of dimethyl sulfoxide, 0.006 mmol of Ir(ppy)3, and 0.45 mmol of 2,6-dimethylpyridine to a reaction tube. Place a 6W red fluorescent lamp 5 cm away from the reaction tube, and stir for 48 hours at 30 °C under N2 protection. After the reaction is complete, concentrate the solution and directly precipitate by column chromatography to obtain the target product.

[0088] Example 15

[0089]

[0090] Synthesis of 4-(7-bromo-4-methylquinoline-2-yl)butyronitrile

[0091] 0.6 mmol of 4-bromo-2-isocyano-1-(prop-1-en-2-yl)benzene, 0.3 mmol of cyclobutanone O-(4-(trifluoromethyl)benzoyl)oxime, 6 mL of dichloromethane, 0.006 mmol of [Ru(bpy)3]Cl2, and 0.45 mmol of dimethylacetamide were added to a reaction tube. An 8W white fluorescent lamp was placed 5 cm away from the reaction tube, and the mixture was stirred for 48 hours under N2 protection at 20 °C. After the reaction was complete, the mixture was concentrated and directly subjected to column chromatography to obtain the target product.

[0092] Example 16

[0093]

[0094] Synthesis of 4-(7-chloro-4-methylquinoline-2-yl)butyronitrile

[0095] 0.9 mmol of 4-chloro-2-isocyano-1-(prop-1-en-2-yl)benzene, 0.6 mmol of cyclobutanone O-(4-(trifluoromethyl)benzoyl)oxime, 6 mL of acetonitrile, 0.006 mmol of rhodamine, and 0.45 mmol of sodium acetate were added to a reaction tube. A 7W green fluorescent lamp was placed 5 cm away from the reaction tube, and the mixture was stirred for 48 hours under N2 protection at 27 °C. After the reaction was complete, the mixture was concentrated and directly subjected to column chromatography to obtain the target product.

[0096] Example 17

[0097]

[0098] Synthesis of 4-(6,7-dimethoxy-4-methylquinoline-2-yl)butyronitrile

[0099] Add 0.6 mmol of 1-isocyano-4,5-dimethoxy-2-(prop-1-en-2-yl)benzene, 0.9 mmol of cyclobutanone O-(4-(trifluoromethyl)benzoyl)oxime, 6 mL of dimethylformamide, 0.006 mmol of [Ir(ppy)2(dtb-bpy)](PF6), and 0.45 mmol of sodium carbonate to a reaction tube. Place a 7W white fluorescent lamp 5 cm away from the reaction tube, maintain the temperature at 24 °C, and stir for 24 hours under N2 protection. After the reaction is complete, concentrate the solution and directly obtain the target product by column chromatography.

[0100] Example 18

[0101]

[0102] Synthesis of 4-(4-methylquinoline-2-yl)valerate

[0103] Add 0.3 mmol of 1-isocyano-2-(prop-1-en-2-yl)benzene, 0.9 mmol of (E)-2-methylcyclobutane-1-one O-(4-(trifluoromethyl)benzoyl)oxime, 6 mL of dimethyl sulfoxide, 0.006 mmol of [Ru(bpy)3](BF4)2, and 0.45 mmol of triethylenediamine to a reaction tube. Place a 7W yellow fluorescent lamp 5 cm away from the reaction tube, and stir for 48 hours under N2 protection at 31 °C. After the reaction is complete, concentrate the solution and directly obtain the target product by column chromatography.

[0104] Example 19

[0105]

[0106] Synthesis of 4-(4-methylquinolin-2-yl)hexanenitrile

[0107] Add 0.9 mmol of 1-isocyano-2-(prop-1-en-2-yl)benzene, 0.3 mmol of (E)-2-ethylcyclobutane-1-one O-(4-(trifluoromethyl)benzoyl)oxime, 6 mL of acetonitrile, 0.006 mmol of fac-Ir(ppy)3, and 0.45 mmol of sodium carbonate to a reaction tube. Place a 7W blue fluorescent lamp 5 cm away from the reaction tube, maintain the temperature at 26 °C, and stir for 24 hours under N2 protection. After the reaction is complete, concentrate the solution and directly precipitate by column chromatography to obtain the target product.

Claims

1. A method for preparing a cyanoalkyl-substituted quinoline compound, characterized in that: The structures of cyanoalkyl-substituted quinoline compounds are shown in general formula I: 、 Ⅰ、 R 1 It can represent hydrogen, alkyl groups with 1-6 carbon atoms, alkoxy groups with 1-6 carbon atoms, fluorine, chlorine, bromine, or iodine; R 2 Represents hydrogen, phenyl, alkyl, cyclohexyl, allyl, or propyne with 1-6 carbon atoms; R 3 Represents hydrogen, alkyl, allyl, propargyl, phenyl, or benzyl groups with 1-6 carbon atoms; X represents C, O, N, or S; Its preparation method is as follows: The reaction formula is as follows: ； AB Ⅰ The reaction process is as follows: The reaction temperature is controlled at 20~35°C. o C. Under a nitrogen-filled protective atmosphere, in an organic solvent, substituted isonitrile A and substituted cyclobutanone oxime B are reacted with alkyl radicals induced by visible light in the presence of a photocatalyst and an alkaline additive to prepare substituted cyanoquinoline compounds of general formula I. The complex formed by ruthenium and bipyridine has the following chemical formula: [Ru(bpy)3]Y2, where Y = SbF6, PF6, BF4, OTf, Br, or Cl; The complex formed by iridium and bipyridine has the following chemical formula: fac -Ir(ppy)3, Ir(ppy)3, or [Ir(ppy)2(dtb-bpy)](PF6); Rhodamine, or eosin Y; The alkaline additive is one or a mixture of more than one of sodium carbonate, potassium carbonate, sodium acetate, 2,6-dimethylpyridine, or triethylenediamine.

2. The preparation method according to claim 1, characterized in that, The compound in question is specifically: 、 、 、 、 、 、 、 、 、 、 。 3. The preparation method according to claim 1, characterized in that: The organic solvent is one or a mixture of more than one of acetonitrile, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, and dichloromethane.

4. The preparation method according to claim 1, characterized in that: The reaction temperature is controlled at 22~25℃. o C.

5. The preparation method according to claim 1, characterized in that: The molar ratio of the reaction between the substituted isonitrile A and the substituted cyclobutanone oxime B is 1-5:1-5, and the catalyst is 0.5-2% of the molar amounts of the two reactants.

6. The preparation method according to claim 1, characterized in that: The visible light mentioned is 7W blue light.

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