A kind of preparation method of cyclohexenone compound

Abstract

The invention discloses a method for preparing a cyclohexenone compound, wherein 2-(iodomethyl)cyclopentanone compounds are used as starting materials, aryl diazonium salts are used as halide ion transfer agents and oxidants, triethylamine is used as a base, and in an acetone solvent, aryl diazonium salts generate aryl radicals, which are then subjected to halide ion transfer and ring-enclosing reactions, and finally oxidized to obtain cyclohexenone compounds. The invention adopts a one-step reaction, simplifies the complex steps in the traditional method, realizes efficient synthesis without transition metal catalysts at room temperature, has a wide range of substrate adaptability, excellent reaction yield and high selectivity, and exhibits significant novel advantages.

Description

Technical Field

[0001] The invention belongs to the technical field of organic synthesis, and specifically relates to a method for preparing cyclohexenone compounds. Background Art

[0002] Cyclohexenone compounds have attracted wide attention due to their rich pharmacological activities, especially in the fields of medicine and agriculture. Studies have shown that these compounds have a variety of biological activities such as anticancer, antimicrobial and anti-epileptic. For example, Tralkoxydim and Clethodim are two highly selective herbicides whose active ingredients are cyclohexenone derivatives. In addition, oral antifungal drugs such as Griseofulvin also rely on the structure of cyclohexenone to achieve their pharmacological effects.

[0003] The diversity of cyclohexenone compounds and their potential in drug development make the study of their synthetic methods particularly important.

[0004] Traditional methods for synthesizing cyclohexenone compounds usually rely on complex reaction pathways and often need to be carried out under high temperature and high pressure conditions, while the selectivity and reaction efficiency of the catalyst are also limited. Common methods for synthesizing cyclohexenone include oxidizing cyclohexene derivatives using oxidants such as hydrogen peroxide and ozone. Although these methods can synthesize cyclohexenone, by-products are often generated during the reaction, making the separation and purification process cumbersome, thereby reducing the overall yield. In addition, some oxidants are highly corrosive and toxic, which poses challenges to operational safety and environmental protection.

[0005] Existing synthetic routes usually rely on transition metal catalysts such as palladium or cobalt and require harsh reaction conditions (such as strong light), which limits its application in large-scale industrial production. Therefore, it is particularly important to develop a simple, efficient, economical and environmentally friendly synthetic method. Summary of the invention

[0006] The purpose of this section is to summarize some aspects of embodiments of the present invention and briefly introduce some preferred embodiments. Some simplifications or omissions may be made in this section and the specification abstract and the invention title of this application to avoid blurring the purpose of this section, the specification abstract and the invention title, and such simplifications or omissions cannot be used to limit the scope of the present invention.

[0007] In view of the above problems and / or the problems existing in the prior art, the present invention is proposed.

[0008] Therefore, the object of the present invention is to overcome the deficiencies in the prior art and provide a method for preparing cyclohexenone compounds.

[0009] In order to solve the above technical problems, the present invention provides the following technical solution: a method for preparing cyclohexenone compounds, comprising:

[0010] Compound A is used as a starting material, and aromatic diazonium salt is used as a halide ion transfer agent and an oxidant to react under alkaline conditions to obtain a cyclohexenone compound;

[0011] Wherein, the structural formula of compound A is:

[0012]

[0013] The structural formula of cyclohexenone compounds is:

[0014]

[0015] Among them, R 1 is H or alkyl;

[0016] R 2 is H or alkyl;

[0017] R 3 is H or alkyl;

[0018] R 4 It is an ester group or an aromatic group.

[0019] As a preferred embodiment of the preparation method of the present invention, the compound A comprises any one of the following structural formulas:

[0020]

[0021] As a preferred embodiment of the preparation method of the present invention, the structural formula of the cyclohexenone compound is any one of the following:

[0022]

[0023] As a preferred embodiment of the preparation method of the present invention, the aromatic diazonium salt comprises at least one of p-methoxyphenyl diazonium tetrafluoroborate, p-tolyl diazonium tetrafluoroborate, p-fluorophenyl diazonium tetrafluoroborate, p-nitrophenyl diazonium tetrafluoroborate and p-N,N-dimethylaminophenyl diazonium tetrafluoroborate.

[0024] As a preferred embodiment of the preparation method of the present invention, the molar ratio of compound A to aryl diazonium salt is 1:1.5 to 1:3.

[0025] As a preferred embodiment of the preparation method of the present invention, the base includes at least one of potassium carbonate, potassium acetate, triethylenediamine, tetramethylguanidine, N,N-diisopropylethylamine and triethylamine.

[0026] As a preferred embodiment of the preparation method of the present invention, the molar ratio of compound A to base is 1:1.5 to 1:3.

[0027] As a preferred embodiment of the preparation method of the present invention, the reaction solvent comprises any one of acetone, dichloromethane, tetrahydrofuran, acetonitrile, methanol and toluene.

[0028] As a preferred embodiment of the preparation method of the present invention, the reaction gas atmosphere is argon, the reaction time is 6 to 15 hours, and the reaction temperature is room temperature.

[0029] Beneficial effects of the present invention:

[0030] (1) The present invention provides a method for preparing cyclohexenone compounds, which can achieve one-step efficient synthesis of such compounds at room temperature without a transition metal catalyst, with wide substrate adaptability, excellent reaction yield and selectivity.

[0031] (2) The synthesis method of the present invention is carried out under mild conditions, avoiding harsh conditions such as high temperature and high pressure, reducing operational risks and improving experimental safety; the reduction reaction of aromatic diazonium salts is combined with the halide ion transfer reaction, reducing the use of harmful oxidants commonly used in traditional synthesis methods, complying with the principles of green chemistry, and reducing the impact on the environment; the optimized reaction conditions enable the synthesis reaction of cyclohexenone to obtain excellent yield and high selectivity, ensuring the purity and yield of the target product.

[0032] (3) The present invention synthesizes cyclohexenone by a one-step method, which reduces the reaction steps and post-treatment process, simplifies the experimental process, and improves the synthesis efficiency; the present method can be applied to a variety of different 2-(iodomethyl)cyclopentanone compounds, exhibits good substrate compatibility, and is convenient for reactions under different chemical environments. These advantages make the present invention have significant technical advantages and application potential in the synthesis of cyclohexenone compounds. BRIEF DESCRIPTION OF THE DRAWINGS

[0033] In order to more clearly illustrate the technical solutions of the embodiments of the present invention, the following briefly introduces the drawings required for describing the embodiments. Obviously, the drawings described below are only some embodiments of the present invention. For ordinary technicians in this field, other drawings can be obtained based on these drawings without creative labor. Among them:

[0034] Figure 1 is the compound 13 obtained in Example 1 of the present invention 1 H NMR spectra.

[0035] Figure 2is the compound 13 obtained in Example 1 of the present invention 13 C NMR spectrum. DETAILED DESCRIPTION

[0036] In order to make the above-mentioned objects, features and advantages of the present invention more obvious and easy to understand, the specific implementation methods of the present invention are described in detail below in conjunction with the embodiments of the specification.

[0037] In the following description, many specific details are set forth to facilitate a full understanding of the present invention, but the present invention may also be implemented in other ways different from those described herein, and those skilled in the art may make similar generalizations without violating the connotation of the present invention. Therefore, the present invention is not limited to the specific embodiments disclosed below.

[0038] Secondly, the term "one embodiment" or "embodiment" as used herein refers to a specific feature, structure, or characteristic that may be included in at least one implementation of the present invention. The term "in one embodiment" that appears in different places in this specification does not necessarily refer to the same embodiment, nor does it refer to a separate or selective embodiment that is mutually exclusive with other embodiments.

[0039] The invention provides a method for preparing cyclohexenone compounds, comprising: using 2-(iodomethyl)cyclopentanone compounds as starting raw materials, utilizing aryl diazonium salts as halide ion transfer agents and oxidants, and using triethylamine as a base to efficiently obtain cyclohexenone compounds in an acetone solvent.

[0040] In the present invention, compound A is derived from cyclopentanone compounds, and aryl diazonium salt is derived from aromatic amine compounds, which are synthesized by simple chemical reactions:

[0041]

[0042] Example 1

[0043] Preparation of compound 13:

[0044]

[0045] A 10 mL Shrek tube with a branch tube and a magnetic stirrer was selected, and 2-(iodomethyl)cyclopentanone compound 1 (56.4 mg, 0.20 mmol) and N,N-dimethylaminophenyl diazonium tetrafluoroborate (94 mg, 0.4 mmol) were added respectively. After replacing the argon gas three times, 2 mL of acetone and triethylamine (56 μL, 0.4 mmol) were added under an argon atmosphere; then the reaction was carried out at room temperature for 12 hours.

[0046] After the reaction is completed, the solvent is removed by rotary evaporation on a rotary evaporator, and then the compound 13 (15.4 mg, 50%) is obtained by rapid silica gel column chromatography (eluent petroleum ether: ethyl acetate volume ratio = 15:1). The product structure characterization data are as follows:

[0047] 1 H NMR (400 MHz, CDCl3): δ 6.71 (t, J = 2.0 Hz, 1H), 3.81 (s, 3H), 2.56 (td, J = 6.0, 2.0 Hz, 2H), 2.47–2.39 (m, 2H), 2.08–2.00 (m, 2H) ppm, see Figure 1 .

[0048] 13 C NMR (101 MHz, CDCl3): δ 200.0, 166.9, 148.7, 133.0, 52.6, 37.6, 24.8, 22.1 ppm, see Figure 2 .

[0049] Example 2: Preparation of Compound 14

[0050]

[0051] Select a 10mL Shrek tube with a branch tube equipped with a magnetic stirrer, add 2-(iodomethyl)cyclopentanone compound 2 (59.2 mg, 0.20 mmol), N,N-dimethylaminophenyl diazonium tetrafluoroborate (94 mg, 0.4 mmol), respectively, replace the argon gas three times, and then add 2mL of acetone and triethylamine (56 μL, 0.4 mmol) under argon atmosphere; then react at room temperature for 12 hours.

[0052] After the reaction, the solvent was removed by rotary evaporation on a rotary evaporator, and then the mixture was purified by rapid silica gel column chromatography (eluent: petroleum ether: ethyl acetate volume ratio = 15:1) to obtain compound 14 (21.9 mg, 65%).

[0053] The product structure characterization data are as follows:

[0054] 1 H NMR (400MHz, CDCl3): δ6.70(d,J=2.4Hz,1H),3.80(s,3H),2.75–2.63(m,1H),2.59–2.45( m,1H),2.45–2.32(m,1H),2.19–2.06(m,1H),1.78–1.64(m,1H),1.13(d,J=6.8Hz,3H)ppm.

[0055] 13C NMR (101MHz, CDCl3): δ202.5, 170.0, 147.9, 132.6, 52.5, 41.4, 30.1, 24.5, 14.6ppm.

[0056] Example 3: Preparation of Compound 15

[0057]

[0058] A 10 mL Shrek tube with a branch tube and a magnetic stirrer was selected, and 2-(iodomethyl)cyclopentanone compound 3 (67.6 mg, 0.20 mmol) and N,N-dimethylaminophenyl diazonium tetrafluoroborate (94 mg, 0.4 mmol) were added respectively. After replacing the argon gas three times, 2 mL of acetone and triethylamine (56 μL, 0.4 mmol) were added under an argon atmosphere; then the reaction was carried out at room temperature for 12 hours.

[0059] After the reaction, the solvent was removed by rotary evaporation on a rotary evaporator, and then the mixture was purified by rapid silica gel column chromatography (eluent: petroleum ether: ethyl acetate volume ratio = 12:1) to obtain compound 15 (25.2 mg, 60%).

[0060] The product structure characterization data are as follows:

[0061] 1 H NMR (400MHz, CDCl3): δ6.71(s,1H),3.82(s,3H),2.76–2.63(m,1H),2.59–2.45(m,1H),2.34–2 .23(m,1H),2.23–2.12(m,1H),1.91–1.71(m,2H),1.43–1.29(m,5H),0.90(t,J=6.4Hz,3H)ppm.

[0062] 13 C NMR (101MHz, CDCl3): δ202.3,167.1,147.6,132.9,52.5,46.3,29.0,28.6,27.2,24.1,22.7,14.0ppm.

[0063] Example 4: Preparation of Compound 16

[0064]

[0065] A 10 mL Shrek tube with a branch tube and a magnetic stirrer was selected, and 2-(iodomethyl)cyclopentanone compound 4 (74.4 mg, 0.20 mmol) and N,N-dimethylaminophenyl diazonium tetrafluoroborate (94 mg, 0.4 mmol) were added respectively. After replacing the argon gas three times, 2 mL of acetone and triethylamine (56 μL, 0.4 mmol) were added under an argon atmosphere; then the reaction was carried out at room temperature for 12 hours.

[0066] After the reaction, the solvent was removed by rotary evaporation and then the mixture was purified by rapid silica gel column chromatography (eluent: petroleum ether: ethyl acetate volume ratio = 10:1) to obtain compound 16 (20.0 mg, 41%).

[0067] The product structure characterization data are as follows:

[0068] 1 H NMR (400MHz, CDCl3): δ7.30–7.22(m,2H),7.22–7.10(m,3H),6.73(s,1H),3.79(s,3H),3.31–3.26(m,1 H),2.70–2.60(m,1H),2.58–2.45(m,2H),2.45–2.33(m,1H),2.07–1.95(m,1H),1.68–1.59(m,1H)ppm.

[0069] 13 C NMR (101MHz, CDCl3): δ201.0,166.9,148.0,139.4,132.8,129.1,128.4,126.3,52.6,48.2,35.0,26.6,24.4ppm.

[0070] Example 5: Preparation of Compound 17

[0071]

[0072] A 10 mL Shrek tube with a branch tube and a magnetic stirrer was selected, and 2-(iodomethyl)cyclopentanone compound 5 (64.0 mg, 0.20 mmol) and N,N-dimethylaminophenyl diazonium tetrafluoroborate (94 mg, 0.4 mmol) were added respectively. After replacing the argon gas three times, 2 mL of acetone and triethylamine (56 μL, 0.4 mmol) were added under an argon atmosphere; then the reaction was carried out at room temperature for 12 hours.

[0073] After the reaction, the solvent was removed by rotary evaporation on a rotary evaporator, and then the mixture was purified by rapid silica gel column chromatography (eluent: petroleum ether: ethyl acetate volume ratio = 15:1) to obtain compound 17 (26.9 mg, 70%).

[0074] The product structure characterization data are as follows:

[0075] 1 H NMR (400MHz, CDCl3): δ6.76–6.71(m,1H),3.82(s,3H),2.85–2.70(m,2H),2.60 –2.37(m,3H),2.37–2.28(m,1H),1.98(t,J=2.4Hz,1H),1.92–1.80(m,1H)ppm.

[0076] 13 C NMR (101MHz, CDCl3): δ199.4,166.7,148.5,132.6,81.5,70.0,52.6,45.4,27.1,24.8,18.7ppm.

[0077] Example 6: Preparation of Compound 18

[0078]

[0079] A 10 mL Shrek tube with a branch tube and a magnetic stirrer was selected, and 2-(iodomethyl)cyclopentanone compound 6 (62.0 mg, 0.20 mmol) and N,N-dimethylaminophenyl diazonium tetrafluoroborate (94 mg, 0.4 mmol) were added respectively. After replacing the argon gas three times, 2 mL of acetone and triethylamine (56 μL, 0.4 mmol) were added under an argon atmosphere; then the reaction was carried out at room temperature for 12 hours.

[0080] After the reaction, the solvent was removed by rotary evaporation on a rotary evaporator, and then the mixture was purified by rapid silica gel column chromatography (eluent: petroleum ether: ethyl acetate volume ratio = 15:1) to obtain compound 18 (24.0 mg, 66%).

[0081] The product structure characterization data are as follows:

[0082] 1 H NMR (400MHz, CDCl3): δ6.64 (s, 1H), 3.81 (s, 3H), 2.58 (td, J = 6.4, 2.0Hz, 2H), 1.85 (t, J = 6.0Hz, 2H), 1.10 (s, 6H) ppm.

[0083] 13 C NMR (101MHz, CDCl3): δ204.8,166.9,146.8,131.8,52.5,41.1,35.6,23.7,22.3ppm.

[0084] Example 7: Preparation of Compound 19

[0085]

[0086] A 10 mL Shrek tube with a branch tube and a magnetic stirrer was selected, and 2-(iodomethyl)cyclopentanone compound 7 (62.0 mg, 0.20 mmol) and N,N-dimethylaminophenyl diazonium tetrafluoroborate (94 mg, 0.4 mmol) were added respectively. After replacing the argon gas three times, 2 mL of acetone and triethylamine (56 μL, 0.4 mmol) were added under an argon atmosphere; then the reaction was carried out at room temperature for 12 hours.

[0087] After the reaction, the solvent was removed by rotary evaporation on a rotary evaporator, and then the mixture was purified by rapid silica gel column chromatography (eluent: petroleum ether: ethyl acetate volume ratio = 15:1) to obtain compound 19 (22.0 mg, 60%).

[0088] The product structure characterization data are as follows:

[0089] 1 H NMR (400MHz, CDCl3): δ6.75 (s, 1H), 3.82 (s, 3H), 2.47 (d, J = 2.0Hz, 2H), 2.29 (s, 2H), 1.06 (s, 6H) ppm.

[0090] 13 C NMR (101MHz, CDCl3): δ200.4,167.1,146.6,132.2,52.6,51.4,38.8,33.5,28.1ppm.

[0091] Example 8: Preparation of Compound 20

[0092]

[0093] A 10 mL Shrek tube with a branch tube and a magnetic stirrer was selected, and 2-(iodomethyl)cyclopentanone compound 8 (59.2 mg, 0.20 mmol) and N,N-dimethylaminophenyl diazonium tetrafluoroborate (94 mg, 0.4 mmol) were added respectively. After replacing the argon gas three times, 2 mL of acetone and triethylamine (56 μL, 0.4 mmol) were added under an argon atmosphere; then the reaction was carried out at room temperature for 12 hours.

[0094] After the reaction, the solvent was removed by rotary evaporation on a rotary evaporator, and then the mixture was purified by rapid silica gel column chromatography (eluent: petroleum ether: ethyl acetate volume ratio = 15:1) to obtain compound 20 (12.8 mg, 38%).

[0095] The product structure characterization data are as follows:

[0096] 1 H NMR (400MHz, CDCl3): δ6.61(s,1H),3.82(s,3H),3.02–2.93(m,1H),2.63–2.51(m,1H),2.40(dt,J=17 .4, 4.5Hz, 1H), 2.17 (tt, J = 13.4, 4.9Hz, 1H), 1.88 (dq, J = 13.6, 4.4Hz, 1H), 1.24 (d, J = 7.0Hz, 3H) ppm.

[0097] 13 C NMR (101MHz, CDCl3): δ200.0,166.8,153.3,131.9,52.5,33.4,29.0,28.7,18.0ppm.

[0098] Example 9: Preparation of Compound 20

[0099]

[0100] A 10 mL Shrek tube with a branch tube and a magnetic stirrer was selected, and 2-(iodomethyl)cyclopentanone compound 9 (60.0 mg, 0.20 mmol) and N,N-dimethylaminophenyl diazonium tetrafluoroborate (94 mg, 0.4 mmol) were added respectively. After replacing the argon gas three times, 2 mL of acetone and triethylamine (56 μL, 0.4 mmol) were added under an argon atmosphere; then the reaction was carried out at room temperature for 12 hours.

[0101] After the reaction, the solvent was removed by rotary evaporation on a rotary evaporator, and then the mixture was purified by rapid silica gel column chromatography (eluent: petroleum ether: ethyl acetate volume ratio = 12:1) to obtain compound 21 (12.4 mg, 36%).

[0102] The product structure characterization data are as follows:

[0103] 1 H NMR (400MHz, CDCl3): δ7.56–7.51(m,2H),7.44–7.38(m,3H),6.45–6.38(m, 1H), 2.78(td,J=6.0,1.2Hz,2H),2.52–2.45(m,2H),2.20–2.12(m,2H)ppm.

[0104] 13 C NMR (101MHz, CDCl3): δ199.9,159.8,138.8,130.0,128.7,126.0,125.4,37.2,28.1,22.8ppm.

[0105] Example 10: Preparation of Compound 22

[0106]

[0107] A 10 mL Shrek tube with a branch tube and a magnetic stirrer was selected, and 2-(iodomethyl)cyclopentanone compound 10 (59.2 mg, 0.20 mmol) and N,N-dimethylaminophenyl diazonium tetrafluoroborate (94 mg, 0.4 mmol) were added respectively. After replacing the argon gas three times, 2 mL of acetone and triethylamine (56 μL, 0.4 mmol) were added under an argon atmosphere; then the reaction was carried out at room temperature for 12 hours.

[0108] After the reaction, the solvent was removed by rotary evaporation on a rotary evaporator, and then the mixture was purified by rapid silica gel column chromatography (eluent: petroleum ether: ethyl acetate volume ratio = 15:1) to obtain compound 22 (23.5 mg, 70%).

[0109] The product structure characterization data are as follows:

[0110] 1 H NMR (400MHz, CDCl3): δ6.69 (t, J=1.6Hz, 1H), 4.23 (q, J=7.2Hz, 2H), 2.54 (td, J= 6.0,1.6Hz,2H),2.45–2.35(m,2H),2.10–1.96(m,2H),1.28(t,J=7.2Hz,3H)ppm.

[0111] 13 C NMR (101MHz, CDCl3): δ200.1,166.4,149.1,132.7,61.5,37.6,24.7,22.0,14.0ppm.

[0112] Example 11: Preparation of Compound 23

[0113]

[0114] A 10 mL Shrek tube with a branch tube and a magnetic stirrer was selected, and 2-(iodomethyl)cyclopentanone compound 11 (81.2 mg, 0.20 mmol) and N,N-dimethylaminophenyl diazonium tetrafluoroborate (94 mg, 0.4 mmol) were added respectively. After replacing the argon gas three times, 2 mL of acetone and triethylamine (56 μL, 0.4 mmol) were added under an argon atmosphere; then the reaction was carried out at room temperature for 12 hours.

[0115] After the reaction, the solvent was removed by rotary evaporation on a rotary evaporator, and then the mixture was purified by rapid silica gel column chromatography (eluent: petroleum ether: ethyl acetate volume ratio = 10:1) to obtain compound 23 (28.4 mg, 51%).

[0116] The product structure characterization data are as follows:

[0117] 1 H NMR (400MHz, CDCl3): δ6.73(s,1H),5.08(t,J=7.2Hz,1H),4.31–4.19(m,2H),2.58(td,J=6.0,1.6Hz,2H),2.49–2.42(m,2H) ),2.11–1.90(m,4H),1.78–1.66(m,4H),1.61–1.45(m,5H),1.41–1.32(m,1H),1.23–1.14(m,1H),0.93(d,J=6.8Hz,3H)ppm.

[0118] 13 C NMR (101MHz, CDCl3): δ200.2,166.6,149.2,132.8,131.5,124.4,64.2,37.7,36.9,35.2,29.4,25.7,25.32,24.8,22.1,19.4,17.7ppm.

[0119] Example 12: Preparation of Compound 24

[0120]

[0121] A 10 mL Shrek tube with a branch tube and a magnetic stirrer was selected, and 2-(iodomethyl)cyclopentanone compound 12 (127.3 mg, 0.20 mmol) and N,N-dimethylaminophenyl diazonium tetrafluoroborate (94 mg, 0.4 mmol) were added respectively. After replacing the argon gas three times, 2 mL of acetone and triethylamine (56 μL, 0.4 mmol) were added under an argon atmosphere; then the reaction was carried out at room temperature for 12 hours.

[0122] After the reaction, the solvent was removed by rotary evaporation on a rotary evaporator, and then the mixture was purified by rapid silica gel column chromatography (eluent: petroleum ether: ethyl acetate volume ratio = 12:1) to obtain compound 24 (40.7 mg, 40%).

[0123] The product structure characterization data are as follows:

[0124] 1H NMR (400MHz, CDCl3): δ6.74(s,1H),5.46–5.36(m,1H),4.82–4.62(m,1H) ,2.60–2.55(m,1H),2.52–2.41(m,2H),2.41–2.32(m,2H),2.09–1.98(m,3 H),1.93–1.80(m,3H),1.63–1.44(m,8H),1.29(s,6H),1.18–1.08(m,6H), 1.05–0.99(m,5H),0.95–0.89(m,4H),0.88–0.84(m,6H),0.68(s,3H)ppm.

[0125] 13 C NMR (101MHz, CDCl3): δ200.3,165.9,149.6,139.2,132.7,123.1,75.4,56.7,56.1,50.0,42.3,39.7,39.5,37.9,37.7,3 6.9,36.6,36.2,35.8,31.9,31.8,29.7,28.2,28.0,27.6,24.8,24.3,23.8,22.8,22.6,22.2,21.0,19.3,18.7,11.8ppm.

[0126] The examples provided above show that the present invention provides a method for preparing cyclohexenone compounds, the reaction conditions are mild, the substrates are universal, and the one-step synthesis efficiency is high, so that the present invention has significant technical advantages and application potential in the synthesis of the compounds.

[0127] It should be noted that the above embodiments are only used to illustrate the technical solutions of the present invention rather than to limit it. Although the present invention has been described in detail with reference to the preferred embodiments, those skilled in the art should understand that the technical solutions of the present invention can be modified or replaced by equivalents without departing from the spirit and scope of the technical solutions of the present invention, which should all be included in the scope of the present invention.

Claims

1. A method for preparing a cyclohexenone compound, characterized in that: include, Compound A is used as a starting material, and aromatic diazonium salt is used as a halide ion transfer agent and an oxidant to react under alkaline conditions to obtain a cyclohexenone compound; Wherein, the compound A includes any of the following structural formulas: The structural formula of the cyclohexenone compound is any one of the following: The aromatic diazonium salt includes at least one of p-methoxyphenyl diazonium tetrafluoroborate, p-tolyl diazonium tetrafluoroborate, p-fluorophenyl diazonium tetrafluoroborate, p-nitrophenyl diazonium tetrafluoroborate, and p-N,N-dimethylaminophenyl diazonium tetrafluoroborate; The base includes at least one of potassium carbonate, potassium acetate, triethylenediamine, tetramethylguanidine, N,N-diisopropylethylamine and triethylamine; The reaction solvent includes any one of acetone, dichloromethane, tetrahydrofuran, acetonitrile, methanol, and toluene; The molar ratio of compound A to aryl diazonium salt is 1:1.5-1:3, the molar ratio of compound A to base is 1:1.5-1:3, the reaction gas atmosphere is argon, the reaction time is 6-15 hours, and the reaction temperature is room temperature.

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