Preparation method of beta-aryl arylacetone compound

Abstract

The invention relates to the technical field of organic chemical synthesis, and discloses a preparation method of a beta-aryl arylacetone compound. The chemical structural formula of the beta-aryl arylacetone compound is shown as a formula (I), the method comprises the following steps: in the presence of a protective gas, an organic solvent and a catalyst, water and a chalcone compound shown as a formula (II) are subjected to a hydrogenation reduction reaction, and a component A is sodium sulfide and / or sodium sulfide nonahydrate. The preparation method provided by the invention has the advantages of mild reaction conditions, high yield, simplicity and convenience in operation, no need of metal and the like.

Description

Technical Field

[0001] This invention relates to the field of organic chemical synthesis technology, specifically to a method for preparing β-aryl arylacetone compounds. Background Technology

[0002] β-aryl aryl acetones are an important class of carbonyl compounds. Substituted β-aryl aryl acetones can acquire a variety of physiological activities, such as anti-tumor, antifungal, and treatment of diabetes, and are important intermediates in the pharmaceutical field.

[0003] Dihydrochalcone and its derivatives are used as low-energy sweeteners in the beverage, confectionery and food manufacturing industries.

[0004] The most mature existing synthetic methods for β-aryl acetones involve selectively hydrogenating α,β-unsaturated ketones to reduce carbon-carbon double bonds under the catalysis of transition metals such as palladium and rhodium to obtain β-aryl acetones.

[0005] CN110256314A discloses a method for preparing β-aryl ketone compounds. The method includes: sequentially adding cyclopropanol, sulfoxide, molecular sieve, sodium trifluoroacetate, and dichloromethane to a pre-dried round-bottom flask; then adding pentafluoropropionic anhydride; stirring at 300-600 rpm at room temperature for 8 hours; quenching with saturated sodium bicarbonate solution; extraction with ethyl acetate; combining the organic phases; concentrating by rotary evaporation; and separating by column chromatography to obtain the target product. However, this method has a narrow substrate scope, only suitable for preparing β-aryl ketone compounds containing sulfides.

[0006] Therefore, there is an urgent need to provide a method for preparing β-aryl arylacetone compounds that has good reaction selectivity, mild reaction conditions, high yield, simple operation, simple post-processing, low cost, and is environmentally friendly. Summary of the Invention

[0007] The purpose of this invention is to provide a method for preparing β-aryl arylacetone compounds that has good reaction selectivity, mild reaction conditions, high yield, simple operation, and a wide range of applicable substrates.

[0008] To achieve the above objectives, the present invention provides a method for preparing β-arylarylacetone compounds of formula (I), the method comprising:

[0009] In the presence of a protective gas, an organic solvent, and a catalyst, water and the chalcone compound represented by formula (II) are subjected to a hydrogenation reduction reaction.

[0010]

[0011] In equations (I) and (II), R 1 and R2 Each of the groups is independently selected from substituted or unsubstituted benzo1,4-dioxane, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or substituted or unsubstituted C2-C5 5-6 membered heterocyclic groups containing a heteroatom as a cyclizing atom, wherein the heteroatom is selected from at least one of nitrogen, oxygen and sulfur atoms.

[0012] R 1 and R 2 The substituents present above are each independently selected from at least one of phenyl, halogen, C1-C6 alkoxy, trifluoromethyl, trifluoromethoxy, C1-C6 alkyl, nitro, ester, carboxyl, amino, sulfone, and hydroxyl groups;

[0013] The molar ratio of the chalcone compound represented by formula (II) to the water is 1:10-30;

[0014] The catalyst is a combination of component A and component B in a molar ratio of 1:0.1-1.5;

[0015] Component A is sodium sulfide and / or sodium sulfide nonahydrate;

[0016] Component B is selected from at least one of pyridine, 4-dimethylaminopyridine, diisopropylethylamine, 1,4-diazabicyclo[2.2.2]octane, 1,8-diazabicycloundec-7-ene, piperazine, N,N-dimethylpiperazine, morpholine, N-methylmorpholine, N-methylpiperidine, triethylamine, potassium sulfide, potassium carbonate, and sodium carbonate.

[0017] Through the above technical solution, the present invention has at least the following beneficial effects:

[0018] (1) The preparation method provided by the present invention has a wide range of raw material sources, good reaction selectivity, wide range of substrates, mild reaction conditions, high yield, simple operation, simple post-processing, low cost and environmental friendliness, and can be carried out using conventional reaction equipment.

[0019] (2) The preparation method provided by the present invention does not require the use of a metal catalyst, but uses water as a hydrogen source to realize the hydrogenation reduction reaction of chalcone compounds.

[0020] (3) The present invention uses a one-step reaction to directly and selectively synthesize the target compound with high yield, overcoming many disadvantages such as complex synthesis process, harsh reaction conditions, poor reaction selectivity and poor functional group tolerance, saving a lot of research and development time and production cycle. Detailed Implementation

[0021] The endpoints and any values ​​of the ranges disclosed herein are not limited to the precise ranges or values, and these ranges or values ​​should be understood to include values ​​close to these ranges or values. For numerical ranges, the endpoint values ​​of the various ranges, the endpoint values ​​of the various ranges and individual point values, and individual point values ​​can be combined with each other to obtain one or more new numerical ranges, which should be considered as specifically disclosed herein.

[0022] In this invention, unless otherwise stated, room temperature means 25±2℃.

[0023] In this invention, unless otherwise specified, groups of the same type have similar interpretations, and will not be described in detail here.

[0024] "C1-C6 alkyl" refers to straight-chain alkyl and branched alkyl with a total of 1-6 carbon atoms (e.g., 1, 2, 3, 4, 5, 6) or cycloalkyl with a total of 3-6 carbon atoms (e.g., 3, 4, 5, 6). Examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, etc.

[0025] "C1-C6 alkoxy groups" refers to straight-chain or branched alkoxy groups with a total number of carbon atoms of 1, 2, 3, 4, 5, or 6. For example, the "C1-C6" group... 1-6 The alkoxy group can be a straight-chain alkoxy group of C1, a straight-chain alkoxy group of C2, a straight-chain alkoxy group or a branched-chain alkoxy group of C3, a straight-chain alkoxy group or a branched-chain alkoxy group of C4, a straight-chain alkoxy group or a branched-chain alkoxy group of C5, a straight-chain alkoxy group or a branched-chain alkoxy group of C6, etc.

[0026] In this invention, substituted or unsubstituted phenyl refers to an unsubstituted phenyl or a phenyl group with R at any position. 1 and R 2 The optional substituents may be used, for example, a phenyl substituted with a C1-C6 alkoxy group or a phenyl substituted with a trifluoromethyl group.

[0027] Halogens include fluorine, chlorine, bromine, and iodine.

[0028] As previously stated, the present invention provides a method for preparing β-arylarylacetone compounds of formula (I), the method comprising:

[0029] In the presence of a protective gas, an organic solvent, and a catalyst, water and the chalcone compound represented by formula (II) are subjected to a hydrogenation reduction reaction.

[0030]

[0031] In equations (I) and (II), R 1 and R2 Each of the groups is independently selected from substituted or unsubstituted benzo1,4-dioxane, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or substituted or unsubstituted C2-C5 5-6 membered heterocyclic groups containing a heteroatom as a cyclizing atom, wherein the heteroatom is selected from at least one of nitrogen, oxygen and sulfur atoms.

[0032] R 1 and R 2 The substituents present above are each independently selected from at least one of phenyl, halogen, C1-C6 alkoxy, trifluoromethyl, trifluoromethoxy, C1-C6 alkyl, nitro, ester, carboxyl, amino, sulfone, and hydroxyl groups;

[0033] The molar ratio of the chalcone compound represented by formula (II) to the water is 1:10-30;

[0034] The catalyst is a combination of component A and component B in a molar ratio of 1:0.1-1.5;

[0035] Component A is sodium sulfide and / or sodium sulfide nonahydrate;

[0036] Component B is selected from at least one of pyridine, 4-dimethylaminopyridine, diisopropylethylamine, 1,4-diazabicyclo[2.2.2]octane, 1,8-diazabicycloundec-7-ene, piperazine, N,N-dimethylpiperazine, morpholine, N-methylmorpholine, N-methylpiperidine, triethylamine, potassium sulfide, potassium carbonate, and sodium carbonate.

[0037] Preferably, the molar ratio of the chalcone compound represented by formula (II) to the water is 1:10-25. The inventors of this invention have found that, under this preferred condition, the preparation method provided by this invention yields a higher output.

[0038] In a preferred embodiment, the molar ratio of component A to component B in the catalyst is 1:0.5-1.3. The inventors of this invention have discovered that, under this preferred embodiment, the preparation method provided by this invention achieves a higher yield.

[0039] Preferably, in the catalyst, component A is sodium sulfide nonahydrate; component B is selected from at least one of potassium carbonate, sodium carbonate, 1,4-diazabicyclo[2.2.2]octane, and 4-dimethylaminopyridine. The inventors of this invention have discovered that, in this preferred embodiment, the preparation method provided by this invention yields a higher output.

[0040] In a preferred embodiment, the molar ratio of the chalcone compound represented by formula (II) to the catalyst is 1:1-6.

[0041] More preferably, the molar ratio of the chalcone compound represented by formula (II) to the catalyst is 1:2-6. The inventors of this invention have found that, under this preferred condition, the preparation method provided by this invention yields a higher output.

[0042] In a preferred embodiment, the organic solvent is selected from at least one of dimethyl sulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, and 1,4-dioxane.

[0043] It should be noted that the present invention does not have any special requirements on the amount of the organic solvent used, and any solvent known in the art can be used. For example, the amount of the organic solvent used is such that the reaction substrate can be completely dissolved.

[0044] Preferably, the conditions for the hydrogenation reduction reaction include at least: a temperature of 80-160°C and a time of 8-24 hours.

[0045] According to a preferred embodiment, in formulas (I) and (II), R 1 and R 2 Each of the groups is independently selected from substituted or unsubstituted benzo1,4-dioxane, substituted or unsubstituted phenyl, or substituted or unsubstituted C2-C5 5-6 membered heterocyclic groups containing a heteroatom as a cyclizing atom, wherein the heteroatom is selected from at least one of nitrogen, oxygen and sulfur atoms.

[0046] R 1 and R 2 The optional substituents are each independently selected from at least one of halogens, C1-C3 alkoxy groups, trifluoromethyl groups, and C1-C3 alkyl groups.

[0047] Preferably, R 1 and R 2 The number of substituents present can be independently 0, 1, 2, or 3. The inventors of this invention have discovered that, in this preferred embodiment, the preparation method provided by this invention yields a higher output.

[0048] Preferably, the protective gas is nitrogen or argon.

[0049] It should be noted that the chalcone compounds represented by formula (II) of this invention can be commercially available or prepared using methods already known in the art. This invention does not have any special requirements, and those skilled in the art should not understand this as a limitation of the invention.

[0050] According to a particularly preferred embodiment, the method further includes purifying the product obtained from the hydrogenation reduction reaction after the hydrogenation reduction reaction.

[0051] The present invention does not have any special requirements for the purification process; any operation known in the art can be used. For example, extraction with an extractant or separation by vacuum filtration can be performed, and impurities can be removed by column chromatography or other methods.

[0052] The present invention will be described in detail below through examples. The structures of the compounds were determined by nuclear magnetic resonance (NMR) instrumentation; in the following examples, unless otherwise specified, all raw materials used are commercially available products.

[0053] Preparation of chalcone compounds represented by formula (II):

[0054] Acetophenone compounds and benzaldehyde were added to a round-bottom flask, and sodium ethoxide / ethanol was used as the reaction system. The reaction was carried out at room temperature for 10 hours. After cooling to room temperature, the mixture was purified by recrystallization to obtain chalcone compounds.

[0055] In the following examples, the amount of chalcone compound used was 1 mmol.

[0056] Example 1

[0057] In the presence of nitrogen, chalcone compounds, water, catalyst and organic solvent were added to a round-bottom flask for hydrogenation reduction. The product obtained after hydrogenation reduction was cooled to room temperature, and ethyl acetate was used as the extraction reaction solution. Then, the product was purified by rotary evaporation under reduced pressure and column chromatography to obtain the target product.

[0058] The types, amounts, and process parameters of the substances involved in this embodiment are listed in Table 1.

[0059] Unless otherwise specified, the remaining embodiments are carried out with reference to the method of Embodiment 1. The difference is that the raw materials and process parameters used in each embodiment are not exactly the same, as detailed in Table 1.

[0060] Table 1

[0061]

[0062]

[0063]

[0064] Note: Molar ratio* indicates the molar ratio of chalcone compounds, water, and catalyst.

[0065] The product characterization data obtained in the above examples are as follows:

[0066] The chemical formulas of the products obtained in Examples 1, 14-16, Comparative Examples 3 and 4 are as follows:

[0067] 11H NMR (600 MHz, DMSO-d6) δ 7.98 (d, J = 7.8 Hz, 2H), 7.63 (t, J = 7.8 Hz, 1H), 7.29–7.26 (m, 4H), 7.19–7.16 (m, 1H), 7.22 (t, J = 7.0 Hz, 1H), 3.37 (t, J = 7.8 Hz, 2H), 2.95 (t, J = 7.8 Hz, 2H). 13 13C NMR (151 MHz, DMSO-d6) δ 199.63, 141.71, 137.07, 133.60, 129.18, 128.86, 128.73, 128.40, 126.33, 39.9, 29.9.

[0068] Example 2:

[0069] 1 1H NMR (600 MHz, CDCl3) δ 7.97 (d, J = 8.4 Hz, 2H), 7.58 - 7.52 (m, 5H), 7.46 - 7.41 (m, 4H), 7.33 - 7.31 (m, 3H), 3.34 (t, J = 7.2 Hz, 2H), 3.11 (t, J = 7.2 Hz, 2H). 13 13C NMR (151 MHz, CDCl3) δ 199.2, 141.0, 140.4, 139.2, 136.9, 133.1, 128.9, 128.8, 128.7, 128.1, 127.3, 127.1, 127.1, 40.4, 29.8.

[0070] Example 3:

[0071] 1 1H NMR (600 MHz, CDCl3) δ 7.96 (d, J = 7.2 Hz, 2H), 7.54 (t, J = 7.2 Hz, 1H), 7.44 (t, J = 7.2 Hz, 2H), 7.29 (d, J = 7.8 Hz, 1H), 7.23 - 7.18 (m, 2H), 7.13 (t, J = 7.2 Hz, 2H), 3.24 (t, J = 7.2 Hz, 2H), 3.21 - 3.16 (m, 1H), 3.10 (t, J = 7.2 Hz, 2H), 1.26 (s, 3H), 1.25 (s, 3H). 13 13C NMR (151 MHz, CDCl3) δ 199.3, 146.7, 138.0, 136.9, 133.2, 129.3, 128.7, 128.1, 126.8, 125.9, 125.5, 40.6, 28.8, 27.1, 24.1.

[0072] Example 4:

[0073] 1 H NMR (600MHz, CDCl3) δ7.95(d,J=7.2Hz,2H),7.53(t,J=7.2Hz,1H),7.43(t,J=7.2Hz,2H),7.21-7. 13(m,4H),3.25(t,J=7.2Hz,2H),3.07(t,J=7.2Hz,2H),2.70-2.66(m,2H),1.23(t,J=7.2Hz,3H). 13 C NMR (151MHz, CDCl3) δ199.4,142.0,138.8,136.9,133.2,129.1,128.7,128.7,128.1,126.6,126.1,77.4,77.2,76.9,40.1,26.9,25.7,15.5.

[0074] Example 5:

[0075] 1 H NMR (600MHz, CDCl3) δ7.97(d,J=7.2Hz,2H),7.56(t,J=7.8Hz,1H),7.46(t,J=7.8Hz ,2H),7.25-7.13(m,4H),3.25(t,J=7.8Hz,2H),3.06(t,J=7.2Hz,2H),2.35(s,3H). 13 C NMR (151MHz, CDCl3) δ199.4,139.4,136.9,136.0,133.1,130.4,128.8,128.7,128.1,126.4,126.2,39.1,27.5,19.4.

[0076] Example 6:

[0077] 1 H NMR (600MHz, CDCl3) δ7.96 (d, J = 7.8Hz, 2H), 7.55 (t, J = 7.2Hz, 1H), 7.45 (t, J = 7.2Hz, 2H), 6.79 (d, J = 8. 4Hz,1H),6.76(s,1H),6.72(d,J=8.4Hz,1H),4.24(s,4H),3.26(t,J=7.8Hz,2H),2.96(t,J=7.2Hz,2H). 13C NMR (151MHz, CDCl3) δ199.3,143.4,141.9,136.9,134.6,133.1,128.6,128.1,121.3,117.2,117.0,64.4,64.3,40.6,29.4.

[0078] Example 7:

[0079] 1 H NMR (600MHz, CDCl3) δ7.97(d,J=7.2Hz,2H),7.57(t,J=7.2Hz,1H),7.46(t,J=7.2Hz,2H),7.13(d,J=5 .4Hz,1H),6.92(t,J=3.0Hz,1H),6.86(d,J=3.0Hz,1H),3.37(t,J=7.8Hz,2H),3.30(t,J=7.2Hz,2H). 13 C NMR (151MHz, CDCl3) δ198.6,143.9,136.8,133.2,128.7,128.1,126.9,124.7,123.4,40.6,24.2.

[0080] Example 8:

[0081] 1 H NMR (600MHz, CDCl3) δ7.97(d,J=7.2Hz,2H),7.54(t,J=7.2Hz,1H),7.44(d,J=7.8Hz,2H),6.80-6.7 9(m,2H),6.73-6.71(m,1H),3.78(s,3H),3.75(s,3H),3.26(t,J=7.2Hz,2H),3.02(t,J=7.2Hz,2H). 13 C NMR (151MHz, CDCl3) δ199.9,153.5,151.8,137.0,132.9,130.8,128.6,128.1,116.5,111.4,111.2,55.8,55.7,39.0,25.9.

[0082] Example 9:

[0083] 1H NMR (600MHz, CDCl3) δ7.28(t,J=7.2Hz,2H),7.23(d,J=6.6Hz,2H),7.19(t,J=7.2Hz,1H),6.81(s,2H),3.06-2.99(m,4H),2.26(s,3H),2.12(s,6H). 13 C NMR (151MHz, CDCl3) δ209.8,141.0,139.5,138.4,132.6,128.5,128.5,126.2,46.4,29.5,21.0,19.0.

[0084] Example 10:

[0085] 1 H NMR (600MHz, CDCl3) δ7.28(t,J=7.2Hz,2H),7.24(d,J=7.2Hz,2H),7.19(t,J=7.2Hz,1H),6.94-6.93(m, 1H),6.78(t,J=2.4Hz,1H),6.10-6.09(m,1H),3.94(s,3H),3.10(t,J=8.4Hz,2H),3.01(t,J=8.4Hz,2H). 13 C NMR (151MHz, CDCl3) δ190.2,141.6,131.0,130.6,128.5,128.4,126.1,119.0,107.9,40.8,37.7,30.9.

[0086] Example 11:

[0087] 1 H NMR (600MHz, CDCl3) δ7.69(d,J=3.6Hz,1H),7.62(d,J=4.8Hz,1H),7.30(t,J=7.8Hz,2H),7.25(d,J=7 .8Hz,2H),7.21(t,J=7.2Hz,1H),7.11(t,J=4.2Hz,1H),3.23(t,J=7.8Hz,2H),3.07(t,J=7.8Hz,2H). 13 C NMR (151MHz, CDCl3) δ192.2,144.2,141.0,133.6,131.8,128.6,128.4,128.1,126.2,41.2,30.4.

[0088] Example 12:

[0089] 1 H NMR(600MHz, CDCl3)δ7.73(d,J=7.2Hz,2H),7.63(d,J=9.20Hz,1H),7.45-7.41(m,1H), 7.30(t,J=7.2Hz,2H),7.27-7.20(m,4H),3.28(t,J=7.2Hz,2H),3.07(t,J=7.2Hz,2H). 13 C NMR (151MHz, CDCl3) δ197.94,197.93,163.71,162.07,141.01,138.97,138.93,130.31,130. 26,128.59,128.43,126.25,123.79,123.77,120.17,120.03,114.88,114.74,40.62,30.00.

[0090] Example 13:

[0091] 1 H NMR (600MHz, CDCl3) δ8.19(s,1H),8.13(d,J=7.8Hz,1H),7.81(d,J=7.8Hz,1H),7.60(t,J=7.8Hz,1H),7.31 (t,J=7.2Hz,2H),7.25(d,J=7.2Hz,3H),7.22(t,J=7.2Hz,1H),3.33(t,J=7.2Hz,2H),3.09(t,J=7.2Hz,2H). 13 C NMR (151MHz, CDCl3) δ197.79,140.87,137.33,131.39,131.15,129.53,129.50,129.48,129.45, 129.31,128.62,128.44,126.31,124.95,124.92,124.90,124.87,124.57,122.77,40.60,29.92.

[0092] Comparative Example 1:

[0093] 1H NMR (600MHz, CDCl3) δ7.94(d,J=8.2Hz,2H),7.56(t,J=7.2Hz,1H),7.45(t,J=7.2Hz,2H), 7.25(d,J=8.4Hz,2H), 7.18(d,J=8.4Hz,2H), 3.28(t,J=7.8Hz,2H), 3.04(t,J=7.8Hz,2H). 13 C NMR (151MHz, CDCl3) δ198.9,139.8,136.8,133.2,131.9,129.9,128.7,128.6,128.0,77.3,77.1,76.8,40.2,29.4.

[0094] Comparative Example 2:

[0095] 1 H NMR (600MHz, CDCl3) δ7.95(d,J=8.4Hz,2H),7.54(t,J=7.8Hz,1H),7.44(t,J=7.8Hz ,2H),7.15-7.10(m,4H),3.27(t,J=7.8Hz,2H),3.03(t,J=7.8Hz,2H),2.31(s,3H). 13 C NMR (151MHz, CDCl3) δ199.4,138.2,136.9,135.7,133.1,129.2,128.6,128.3,128.0,40.6,29.7,21.0.

[0096] The conversion rates of the reactions in each example are shown in Table 2.

[0097] The conversion rate is the ratio of the amount of chalcone compound participating in the reaction to the amount of chalcone compound initially added.

[0098] Table 2

[0099] Instance number Conversion rate Example 1 83％ Example 2 76％ Example 3 80％ Example 4 81％ Example 5 85％ Example 6 78％ Example 7 77％ Example 8 80％ Example 9 75％ Example 10 75％ Example 11 72％ Example 12 75％ Example 13 77％ Example 14 50％ Example 15 45％ Example 16 40％ Comparative Example 1 23％ Comparative Example 2 19％ Comparative Example 3 25％ Comparative Example 4 20％

[0100] As can be seen from the results in Table 2, the preparation method provided by this invention has the advantages of mild reaction conditions, high yield, simple operation, and no need to use metals.

[0101] The preferred embodiments of the present invention have been described in detail above; however, the present invention is not limited thereto. Within the scope of the inventive concept, various simple modifications can be made to the technical solutions of the present invention, including combinations of various technical features in any other suitable manner. These simple modifications and combinations should also be considered as the content disclosed in the present invention and are all within the protection scope of the present invention.

Claims

1. A method for preparing β-arylacetone compounds of formula (I), characterized in that, The method includes: In the presence of a protective gas, an organic solvent, and a catalyst, water and the chalcone compound represented by formula (II) are subjected to a hydrogenation reduction reaction. In equations (I) and (II), R 1 and R 2 Each of the groups is independently selected from substituted or unsubstituted benzo1,4-dioxane, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or substituted or unsubstituted C2-C5 5-6 membered heterocyclic groups containing a heteroatom as a cyclizing atom, wherein the heteroatom is selected from at least one of nitrogen, oxygen and sulfur atoms. R 1 and R 2 The substituents present above are each independently selected from at least one of phenyl, halogen, C1-C6 alkoxy, trifluoromethyl, trifluoromethoxy, C1-C6 alkyl, nitro, ester, carboxyl, amino, sulfone, and hydroxyl groups; The molar ratio of the chalcone compound represented by formula (II) to the water is 1:10-30; The catalyst is a combination of component A and component B in a molar ratio of 1:0.1-1.5; Component A is sodium sulfide and / or sodium sulfide nonahydrate; Component B is selected from at least one of pyridine, 4-dimethylaminopyridine, diisopropylethylamine, 1,4-diazabicyclo[2.2.2]octane, 1,8-diazabicycloundec-7-ene, piperazine, N,N-dimethylpiperazine, morpholine, N-methylmorpholine, N-methylpiperidine, triethylamine, potassium sulfide, potassium carbonate, and sodium carbonate.

2. The method according to claim 1, characterized in that, The molar ratio of the chalcone compound represented by formula (II) to the water is 1:10-25.

3. The method according to claim 1 or 2, characterized in that, In the catalyst, the molar ratio of component A to component B is 1:0.5-1.

3.

4. The method according to any one of claims 1-3, characterized in that, In the catalyst, component A is sodium sulfide nonahydrate; component B is selected from at least one of potassium carbonate, sodium carbonate, 1,4-diazabicyclo[2.2.2]octane, and 4-dimethylaminopyridine.

5. The method according to any one of claims 1-4, characterized in that, The molar ratio of the chalcone compound represented by formula (II) to the catalyst is 1:1-6.

6. The method according to claim 5, characterized in that, The molar ratio of the chalcone compound represented by formula (II) to the catalyst is 1:2-6.

7. The method according to any one of claims 1-6, characterized in that, The organic solvent is selected from at least one of dimethyl sulfoxide, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone and 1,4-dioxane.

8. The method according to any one of claims 1-7, characterized in that, The conditions for the hydrogenation reduction reaction include at least the following: a temperature of 80-160℃ and a time of 8-24h.

9. The method according to any one of claims 1-8, characterized in that, In equations (I) and (II), R 1 and R 2 Each of the groups is independently selected from substituted or unsubstituted benzo1,4-dioxane, substituted or unsubstituted phenyl, or substituted or unsubstituted C2-C5 5-6 membered heterocyclic groups containing a heteroatom as a cyclizing atom, wherein the heteroatom is selected from at least one of nitrogen, oxygen and sulfur atoms. R 1 and R 2 The optional substituents are each independently selected from at least one of halogens, C1-C3 alkoxy groups, trifluoromethyl groups, and C1-C3 alkyl groups.

10. The method according to any one of claims 1-9, characterized in that, R 1 and R 2 The number of substituents that can be selected can be 0, 1, 2 or 3 independently.

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