An arylmethyl sulfone compound and a method for synthesizing the same

Abstract

The application belongs to the technical field of synthetic chemistry, and relates to an arylmethyl sulfone compound and a synthesis method thereof. The application takes an imidazopyridine compound as a reaction substrate, takes sodium sulfinate as a sulfone reagent, takes DMA as a methylene source, and directly obtains the arylmethyl sulfone compound through one-step reaction under the action of a catalyst and an oxidant. The synthesis method has the advantages of rapid reaction, low cost of raw materials, simple operation and high yield. The arylmethyl sulfone compound constructed by the application is an important skeleton of many drugs, bioactive molecules and natural products, and the synthesis method provides a widely applicable preparation method for the synthesis of the compounds.

Description

Technical Field

[0001] This invention relates to an aryl methyl sulfone compound and its synthesis method, belonging to the field of synthetic chemistry technology, and is widely used in the synthesis research of natural products and drugs. Background Technology

[0002] Sulfones are important components of organosulfides and form the core skeleton of many drugs. For example, Aprestil, containing a methyl sulfone structure, is a drug for treating psoriasis; heterocyclic polyfluoroalkyl sulfones are novel nematicides with good control effects against parasitic nematodes on various crops; some novel antagonists of bacterial quorum sensing in Vibrio harveyi also contain sulfone skeletons; sulfone derivatives have also been found to be potent inhibitors of several enzymes, such as LpxC and MMP. Pharmaceutically active sulfones include, but are not limited to, the following substances:

[0003]

[0004] Compounds represented by DMF, due to their special structure, can insert a group from themselves into other molecules to form new compounds. The groups they can provide include NMe2, Me2NCO, H, C, O, CO, CHO, HCO2, CN, etc. This class of compounds specifically includes the following:

[0005]

[0006] Synthetic methods for sulfones have been reported in the literature. The most common method is the direct oxidation of sulfides. Among many oxidants, hydrogen peroxide is widely used due to its advantages such as low cost, high atom economy, no harmful byproducts, and safe operation. In 2005, Strukul's group used water as a solvent (Scarso A, Strukul G. Advanced Synthesis & Catalysis, 2005, 347(9):1227-1234.) and a Pt / BINAP / H2O2 / surfactant (SDS) system to prepare sulfones by oxidation of sulfides. In 2007, Katsuki et al. (Egami H, Katsuki T. Journal of the American Chemical Society, 2007, 2007(10):1066-1066.) used Fe(salan) complex as a catalyst and hydrogen peroxide as an oxidant to prepare sulfones. This method has high yield, wide substrate applicability, and mild conditions. In 2010, Rahimizadeh et al. used pure or Presley-type heteropolyacid-modified nano-titanium dioxide as a catalyst and hydrogen peroxide as an oxidant to convert sulfides into sulfones or sulfoxides. The reaction conditions were mild, the catalyst could be recycled and reused, and its catalytic activity remained essentially unchanged (Rahimizadeh M, Rajabzadeh G, Khatami SM, et al. Journal of Molecular Catalysis A Chemical, 2010, 323(1-2):59-64.).

[0007]

[0008] In 2014, Wu et al. synthesized diaryl sulfones at room temperature using Cu(OAc)2 as a catalyst, arylboronic acid and sulfonyl hydrazine as raw materials, and ethanol as a solvent. The yield of this reaction was moderate (Wu XM, Wang Y. Synlett, 2014, 25(08): 1163-1167.). In 2018, Wu et al. prepared diaryl sulfones at 100℃ using Cu(OAc)2·H2O as a catalyst, arylsulfonyl hydrazine and aryl halides as raw materials, and PEG-400 as a solvent. Generally, aryl iodides with electron-withdrawing substituents have higher yields (such as F, Cl, Br), while aryl iodides with electron-donating substituents have slightly lower yields (such as Me, OMe, SCH3, NH2) (Wu X, Yan W. New Journal of Chemistry, 2018, 42(13): 10953-10957.).

[0009]

[0010] In 2014, Jiang et al. prepared vinyl sulfone using CuCl as a catalyst, sulfonyl hydrazine and aryl ethylene as raw materials, and DMSO as a solvent at 100℃ (Li X, Xu Y, Wu W, et al. Chemistry-A European Journal, 2014, 20(26):7911-7915.). In the same year, Lei et al. synthesized vinyl sulfone under the combined action of iodine and TBHP (Tang S, Wu Y, et al. Chemical Communications, 2014, 50(34):4496-4499.). In 2017, Lu et al. prepared vinyl sulfone using copper salt as a catalyst and the reaction of terminal alkyne and aryl sulfonyl hydrazine (Ding, Zong-Cang, Lu-Chuan, et al. Synthesis: International Journal of Methods in Synthetic Organic Chemistry, 2017, 49(7):1575-1582.). Depending on the source of copper(II), two different vinyl sulfones, (E)-vinyl sulfone and (Z)-β-chlorovinyl sulfone, can be obtained. The addition of cyclohexanone is crucial for this reaction. In 2018, Huang et al. used elemental iodine as a catalyst, TBHP as an oxidant, and sodium carbonate as an additive to obtain the target compound at 90 °C under a nitrogen atmosphere (Zhan Z, Ma H, Wei D, et al. Tetrahedron Letters, 2018, 59(14): 1446-1450.).

[0011] In addition, olefins can also participate in such reactions through in-situ decarboxylation. In 2015, Zhang et al. used iron and copper as co-catalysts to decarboxylate terminal alkyne derivatives and react them with sulfonyl hydrazine to obtain the target compound in high yield (Rong G, Mao J, Yan H, et al. The Journal of Organic Chemistry, 2015, 80(9):4697-4703.). In the same year, Singh et al. used cinnamic acid and sulfonyl hydrazine as raw materials and reacted them at room temperature for 1 h in an iodine / TBHP / DBU system to obtain the target product. The mechanism of sulfone synthesis from cinnamic acid and sulfonyl hydrazine is generally considered to be that sulfonyl hydrazine loses one molecule of nitrogen under the action of an oxidant to generate a sulfonyl radical, which then adds to cinnamic acid and subsequently decarboxylates to generate the target compound (Singh R, Allam BK, Singh N, et al. Organic Letters, 2015, 17(11):2656-2659.).

[0012]

[0013] In 2021, Rode et al. used 2-phenylimidazo[1,2,-α]pyridine as a starting material, sodium sulfite as a sulfone source, DMSO as a carbon source, and Selectfluor as an oxidant to generate a sulfone compound with an additional carbon atom. In 2022, Tang et al. used 2-phenylimidazo[1,2,-α]pyridine as a starting material, sodium sulfite as a sulfone source, CHOCOOH as a carbon source, and water as a solvent to generate a sulfone compound with an inserted carbon atom.

[0014]

[0015] In summary, although there are various methods for preparing sulfone compounds, current methods often involve harsh reaction conditions, require inert gas protection, and have low yields.

[0016] Therefore, those skilled in the art have been researching and exploring in hopes of finding new, more efficient methods for synthesizing sulfone compounds. Summary of the Invention

[0017] In a first aspect, the present invention provides a method for synthesizing aryl methyl sulfone compounds, wherein the chemical reaction formula of the synthesis method is as follows:

[0018]

[0019] In Formula I, Ar is selected from 2-phenylimidazo[1,2-α]pyridine, 2-(2-methyl)phenylimidazo[1,2-α]pyridine, 2-(3-methyl)phenylimidazo[1,2-α]pyridine, 2-(4-chlorophenyl)imidazo[1,2-α]pyridine, 2-(4-bromophenyl)imidazo[1,2-α]pyridine, 2-(4-nitrophenyl)imidazo[1,2-α]pyridine, 6-methyl-2-phenylimidazo[1,2-α]pyridine, 7-bromo- One of the following: 2-phenylimidazo[1,2-α]pyridine, 8-methyl-2-phenylimidazo[1,2-α]pyridine, 2-(2-thiophene)imidazo[1,2-α]pyridine, 2-(2-furan)imidazo[1,2-α]pyridine, 2-tert-butylimidazo[1,2-α]pyridine, 6-phenyl-2,3-dihydroimidazo[2,1-β]thiazole, 6-phenylimidazo[2,1-β]thiazole, and 1-phenyl-3-methyl-5-amino-1H-pyrazole;

[0020] R is selected from one of methyl, phenyl, p-tolyl, 4-fluorophenyl, 4-chlorophenyl, 4-bromophenyl, 4-methoxyphenyl, 2-chlorophenyl, cyclopropyl, p-trifluoromethylphenyl, thienyl, and pyridyl.

[0021] The reaction steps of the synthesis method are as follows: the raw material aromatic base compound Ar-H and sodium alkyl sulfinate RSO2Na, as well as the catalyst FeCl3 and oxidant K2S2O8, are added to a mixed system of DMA and water, and reacted at 110-130℃ until the raw material disappears. The mixture is then separated and purified to obtain aryl methyl sulfone compounds; the DMA is N,N-dimethylacetamide.

[0022] Preferably, the molar ratio of the aromatic base, sodium alkyl sulfinate, catalyst, and oxidant is 1:(1.1-2):0.1:2.5.

[0023] Furthermore, in the DMA and water mixture system, the volume ratio of DMA to water is 2:1.

[0024] Furthermore, the reaction temperature is 120°C.

[0025] Furthermore, the concentration of the raw material aromatic base is 0.1–0.4 mol / L.

[0026] In a second aspect, the present invention provides an aryl methyl sulfone compound prepared according to the synthesis method described in the first aspect.

[0027] Preferably, the arylmethyl sulfone compounds specifically include the following compounds:

[0028]

[0029] The beneficial effects of this invention are as follows: This reaction, using sodium sulfite as a sulfur source and imidazopyridine as a reaction substrate, with the addition of a catalyst (ferric chloride) and an oxidant (potassium persulfate), efficiently synthesizes sulfone compounds with an inserted carbon atom. Compared with the prior art, the advantages of the synthesis method described in this invention are as follows:

[0030] (1) The present invention uses sodium sulfite as a sulfone source, which is stable and easy to store;

[0031] (2) The present invention uses N,N-dimethylacetamide as a carbon source, and the raw materials are readily available;

[0032] (3) The synthesis method described in this invention has high yield, simple operation, and wide substrate applicability;

[0033] (4) The synthesis method described in this invention does not require inert gas protection and is not sensitive to air humidity;

[0034] (5) The synthesis method described in this invention can provide a sulfone compound with one more carbon atom than the traditional method.

[0035] The sulfone compounds with an inserted carbon atom that are efficiently constructed by this invention are important backbones for many drugs and bioactive molecules. The synthetic method described in this invention provides a widely applicable preparation method for the synthesis of such compounds. Attached Figure Description

[0036] Figures 1-2 The NMR spectra of the synthesized products in Examples 1 and 2 are shown in (a). 1 H NMR(b) 13 C NMR;

[0037] Figure 3 The NMR spectrum of the synthesized product in Example 3 is shown in (a). 1 H NMR(b) 13 C NMR(c) 19 F NMR)

[0038] Figures 4 to 29 The NMR spectra of the synthesized products in Examples 4-29 are shown in (a). 1 H NMR(b) 13 C NMR. Detailed Implementation

[0039] Example 1

[0040] Synthesized from 2-phenylimidazo[1,2-α]pyridine (1a) and sodium p-tolylsulfinate (2a):

[0041]

[0042] 0.6 mmol of 2-phenylimidazo[1,2,-α]pyridine (1a), 0.66 mmol of sodium p-toluenesulfinate (2a), 0.06 mmol of FeCl3, 1.5 mmol of potassium persulfate, and 3 mL of solvent (DMA:H2O = 2:1) were added to a reaction flask, and the reaction was carried out at 120 °C until the starting material disappeared. The mixture was extracted three times with saturated brine and ethyl acetate. The organic phases were combined, dried, and separated by column chromatography to give a white solid in 90% yield.

[0043] 1 H NMR (300MHz, CDCl3) δ8.45(d,J=6.9Hz,1H),7.67(d,J=9.1Hz,1H),7.38(d,J=8.3Hz, 2H),7.35–7.27(m,6H),7.09(d,J=8.0Hz,2H),6.94(s,1H),4.88(s,2H),2.36(s,3H). 13C NMR (75MHz, CDCl3) δ147.42,146.00,145.33,134.22,133.03,129.84,128.34,1 28.23,128.16,128.14,126.03,124.98,117.50,112.92,108.29,52.69,21.67.

[0044] Example 2

[0045] Synthesized using 2-phenylimidazo[1,2-α]pyridine (1a) and sodium phenylsulfinate (2b) as raw materials:

[0046]

[0047] 0.6 mmol of 2-phenylimidazo[1,2-α]pyridine (1a), 0.9 mmol of sodium phenylsulfinate (2b), 0.06 mmol of FeCl3, 1.5 mmol of potassium persulfate, and 3 mL of solvent (DMA:H2O = 2:1) were added to a reaction flask, and the reaction was carried out at 120 °C until the starting material disappeared. Saturated brine was added, and the mixture was extracted three times with ethyl acetate. The combined organic phases were dried and separated by column chromatography to give a white solid in 88% yield.

[0048] 1 H NMR (300MHz, CDCl3) δ8.47(d,J=7.0Hz,1H),7.71(d,J=9.0Hz,1H),7.59–7.52(m,3H),7.39–7.29(m,8H),6.96(td,J=6.9,1.2Hz,1H),4.91(s,2H). 13 C NMR (75MHz, CDCl3) δ147.67,146.04,137.51,134.26,132.99,129.28,128.5 5,128.28,128.25,128.19,126.08,124.96,117.57,112.97,108.03,52.74.

[0049] Example 3

[0050] Synthesized using 2-phenylimidazo[1,2-α]pyridine (1a) and sodium p-fluorophenyl sulfinate (2c) as raw materials (3c):

[0051]

[0052] 0.6 mmol of 2-phenylimidazo[1,2-α]pyridine (1a), 1.2 mmol of sodium p-fluorophenyl sulfinate (2c), 0.06 mmol of FeCl3, 1.5 mmol of potassium persulfate, and 3 mL of solvent (DMA:H2O = 2:1) were added to a reaction flask, and the reaction was carried out at 120 °C until the starting material disappeared. Saturated brine was added, and the mixture was extracted three times with ethyl acetate. The organic phases were combined, dried, and separated by column chromatography to give a white solid in 78% yield.

[0053] 1 H NMR(300MHz, CDCl3)) δ8.36(d,J=6.9Hz,1H),7.64(d,J=9.0Hz,1H),7.29–7.23(m,5H),7.22–7.10(m,5H),6.92(td,J=6.9,1.2Hz,1H),4.87(s,2H). 13 C NMR (75MHz, CDCl3) δ167.79,164.38,147.38,146.08,132.95,131.07,130.93,128.5 2,128.26,128.06,126.11,124.84,117.60,116.57,116.27,112.99,107.91,52.35. 19 FNMR (282MHz, CDCl3) δ -102.63.

[0054] Example 4

[0055] Synthesized using 2-phenylimidazo[1,2-α]pyridine (1a) and sodium p-chlorophenylsulfinate (2d) as raw materials (3d):

[0056]

[0057] 0.6 mmol of 2-phenylimidazo[1,2-α]pyridine (1a), 1.2 mmol of sodium p-chlorophenylsulfinate (2d), 0.06 mmol of FeCl3, 1.5 mmol of potassium persulfate, and 3 mL of solvent (DMA:H2O = 2:1) were added to a reaction flask, and the reaction was carried out at 120 °C until the starting material disappeared. Saturated brine was added, and the mixture was extracted three times with ethyl acetate. The combined organic phases were dried and separated by column chromatography to give a white solid in 80% yield.

[0058] 1H NMR(300MHz, CDCl3)δ8.43(d,J=6.8Hz,1H),7.77–7.67(m,1H),7.40–7.28( m,6H),7.25(s,2H),7.21–7.14(m,2H),6.97(d,J=6.8Hz,1H),4.93(s,2H). 13 C NMR (75MHz, CDCl3) δ147.06,145.93,141.27,135.26,132.50,129.60,129.4 8,128.66,128.51,128.14,126.61,124.95,117.60,113.40,107.98,52.27.

[0059] Example 5

[0060] Synthesized using 2-phenylimidazo[1,2-α]pyridine (1a) and sodium p-bromophenylsulfinate (2e) as starting materials (3e):

[0061]

[0062] 0.6 mmol of 2-phenylimidazo[1,2-α]pyridine (1a), 1.2 mmol of sodium p-bromophenylsulfinate (2e), 0.06 mmol of FeCl3, 1.5 mmol of potassium persulfate, and 3 mL of solvent (DMA:H2O = 2:1) were added to a reaction flask, and the reaction was carried out at 120 °C until the starting material disappeared. Saturated brine was added, and the mixture was extracted three times with ethyl acetate. The combined organic phases were dried and separated by column chromatography to give a white solid in 82% yield.

[0063] 1 H NMR (300MHz, CDCl3) δ8.39(d,J=6.9Hz,1H),7.65(d,J=9.1Hz,1H),7.31(ddd,J=7.8,4.0,2.3Hz,6H),7.26–7.15(m,4H),6.93(td,J=6.8,1.2Hz,1H). 13 C NMR (75MHz, CDCl3) δ147.37,146.11,135.75,132.77,132.36,129.91,129.5 6,128.57,128.32,128.06,126.26,124.84,117.63,113.13,107.82,52.17.

[0064] Example 6

[0065] Synthesized using 2-(2-methyl)phenylimidazo[1,2-α]pyridine (1b) and sodium p-tolylsulfinate (2a) as starting materials (3f):

[0066]

[0067] 0.6 mmol of 2-(2-methyl)phenylimidazo[1,2-α]pyridine (1b), 0.66 mmol of sodium p-tolylsulfinate (2a), 0.06 mmol of FeCl3, 1.5 mmol of potassium persulfate, and 3 mL of solvent (DMA:H2O = 2:1) were added to a reaction flask, and the reaction was carried out at 120 °C until the starting material disappeared. Saturated brine was added, and the mixture was extracted three times with ethyl acetate. The combined organic phases were dried and separated by column chromatography to give a white solid in 82% yield.

[0068] 1 H NMR (300MHz, CDCl3) δ8.44(d,J=6.9Hz,1H),7.56(d,J=9.1Hz,1H),7.22(dd,J=9.0,7.1Hz,3H),7.12(td,J=7.5,1.4Hz,1H),7.02(d, J=7.6Hz,3H),6.94(t,J=7.3Hz,1H),6.86(td,J=6.9,1.2Hz,1H),6.62(dd,J=7.5,1.3Hz,1H),4.64(s,2H),2.31(s,3H),1.91(s,3H). 13 C NMR (75MHz, CDCl3) δ147.69,145.66,145.06,137.38,134.49,131.82,130.30,129.87, 128.43,128.05,125.82,125.29,125.15,117.48,112.86,109.31,52.29,21.67,20.00.

[0069] Example 7

[0070] Synthesized using 2-(3-methyl)phenylimidazo[1,2-α]pyridine (1c) and sodium p-tolylsulfinate (2a) as raw materials (3g):

[0071]

[0072] 0.6 mmol of 2-(3-methyl)phenylimidazo[1,2-α]pyridine (1c), 0.66 mmol of sodium p-tolylsulfinate (2a), 0.06 mmol of FeCl3, 1.5 mmol of potassium persulfate, and 3 mL of solvent (DMA:H2O = 2:1) were added to a reaction flask, and the reaction was carried out at 120 °C until the starting material disappeared. Saturated brine was added, and the mixture was extracted three times with ethyl acetate. The combined organic phases were dried and separated by column chromatography to give a white solid in 88% yield.

[0073] 1 H NMR (300MHz, CDCl3) δ8.38(d,J=6.9Hz,1H),7.59(dd,J=9.1,1.2Hz,1H),7.30(d,J=8.3Hz,2H),7.25–7.20(m,1H) ,7.09(d,J=1.3Hz,1H),7.02(d,J=9.1Hz,5H),6.84(td,J=6.9,1.2Hz,1H),4.79(s,2H),2.27(s,3H),2.23(s,3H). 13 C NMR (75MHz, CDCl3) δ147.50,145.92,145.26,138.09,134.39,132.84,129.84,128.95, 128.26,128.21,126.06,125.22,125.04,117.46,112.93,108.27,52.81,21.70,21.47.

[0074] Example 8

[0075] Synthesized using 2-(4-chlorophenyl)imidazo[1,2-α]pyridine (1d) and sodium p-methylsulfinate (2a) as starting materials (3h):

[0076]

[0077] 0.6 mmol of 2-(4-chloro)phenylimidazo[1,2-α]pyridine (1d), 0.66 mmol of sodium p-methylphenylsulfinate (2a), 0.06 mmol of FeCl3, 1.5 mmol of potassium persulfate, and 3 mL of solvent (DMA:H2O = 2:1) were added to a reaction flask, and the reaction was carried out at 120 °C until the starting material disappeared. Saturated brine was added, and the mixture was extracted three times with ethyl acetate. The combined organic phases were dried and separated by column chromatography to give a white solid in 85% yield.

[0078] 1H NMR (300MHz, CDCl3) δ8.33(d,J=7.0Hz,1H),7.58(d,J=9.1Hz,1H),7.33(d,J=8.3Hz,2H), 7.26–7.16(m,5H),7.04(d,J=8.0Hz,2H),6.86(t,J=7.3Hz,1H),4.75(s,2H),2.30(s,3H). 13 C NMR (75MHz, CDCl3) δ210.22,146.05,146.00,145.62,134.36,134.30,131.55,129. 94,129.50,128.59,128.24,126.39,124.93,117.53,113.19,108.46,52.64,21.72.

[0079] Example 9

[0080] Synthesized using 2-phenylimidazo[1,2-α]pyridine (1a) and sodium p-methoxyphenylsulfinate (2f) as raw materials (3i):

[0081]

[0082] 0.6 mmol of 2-phenylimidazo[1,2-α]pyridine (1a), 1.2 mmol of sodium p-methoxyphenylsulfinate (2f), 0.06 mmol of FeCl3, 1.5 mmol of potassium persulfate, and 3 mL of solvent (DMA:H2O = 2:1) were added to a reaction flask, and the reaction was carried out at 120 °C until the starting material disappeared. Saturated brine was added, and the mixture was extracted three times with ethyl acetate. The combined organic phases were dried and separated by column chromatography to give a white solid in 90% yield.

[0083] 1 H NMR(300MHz, CDCl3)δ8.36(d,J=7.0Hz,1H),7.59(d,J=9.1Hz,1H),7.34–7.28(m,2H),7.2 6–7.18(m,6H),6.85(td,J=6.8,1.2Hz,1H),6.69–6.58(m,2H),4.79(s,2H),3.72(s,3H). 13 C NMR (75MHz, CDCl3) δ164.10,147.20,145.90,132.99,130.30,128.37,128. 15,128.10,125.99,124.92,117.47,114.34,112.90,108.47,55.63,52.68

[0084] Example 10

[0085] Synthesized using 2-phenylimidazo[1,2-α]pyridine (1a) and sodium o-chlorophenylsulfinate (2g) as raw materials (3j):

[0086]

[0087] 0.6 mmol of 2-phenylimidazo[1,2-α]pyridine (1a), 1.2 mmol of sodium 2-chlorophenylsulfinate (2 g), 0.06 mmol of FeCl3, 1.5 mmol of potassium persulfate, and 3 mL of solvent (DMA:H2O = 2:1) were added to a reaction flask, and the reaction was carried out at 120 °C until the starting material disappeared. Saturated brine was added, and the mixture was extracted three times with ethyl acetate. The combined organic phases were dried and separated by column chromatography to give a white solid in 74% yield.

[0088] 1 H NMR (300MHz, CDCl3) δ8.48(d,J=7.0Hz,1H),7.73(dd,J=7.9,1.7Hz,1H),7.66(d,J=9.1Hz,1H),7.44(d, J=3.8Hz,3H),7.35–7.27(m,5H),7.24(dd,J=7.9,1.2Hz,1H),6.95(td,J=6.9,1.2Hz,1H),5.14(s,2H). 13 C NMR (75MHz, CDCl3) δ148.07,146.22,135.41,135.27,133.08,132.91,132.04,132.0 1,128.67,128.52,128.41,127.37,126.24,125.10,117.59,113.07,107.48,50.37.

[0089] Example 11

[0090] Synthesized using 2-phenylimidazo[1,2-α]pyridine (1a) and sodium cyclopropylsulfinate (2h) as starting materials (3h):

[0091]

[0092] 0.6 mmol of 2-phenylimidazo[1,2-α]pyridine (1a), 0.9 mmol of sodium cyclopropyl sulfinate (2h), 0.06 mmol of FeCl3, 1.5 mmol of potassium persulfate, and 3 mL of solvent (DMA:H2O = 2:1) were added to a reaction flask, and the reaction was carried out at 120 °C until the starting material disappeared. Saturated brine was added, and the mixture was extracted three times with ethyl acetate. The combined organic phases were dried and separated by column chromatography to give a white solid in 80% yield.

[0093] 1 H NMR(300MHz, CDCl3)δ8.40(d,J=7.0Hz,1H),7.79(dd,J=8.2,1.4Hz,2H),7.71(d,J=9.1Hz,1H),7.52–7.38(m,3H),7.36–7.28(m,1H), 6.93(dd,J=6.9,1.1Hz,1H),4.86(s,2H),2.12(ddd,J=12.8,8.0,4.8Hz,1H),1.00(dd,J=4.7,2.1Hz,2H),0.68(dd,J=7.9,2.2Hz,2H). 13 C NMR (75MHz, CDCl3) δ147.08,145.99,133.51,129.00,128.64,128.53,126.21,124.91,117.52,113.08,108.12,49.91,28.80,4.98.

[0094] Example 12

[0095] Synthesized using 2-phenylimidazo[1,2-α]pyridine (1a) and sodium p-trifluoromethylphenylsulfinate (2i) as raw materials (3i):

[0096]

[0097] 0.6 mmol of 2-phenylimidazo[1,2-α]pyridine (1a), 1.2 mmol of sodium p-trifluoromethylphenylsulfinate (2i), 0.06 mmol of FeCl3, 1.5 mmol of potassium persulfate, and 3 mL of solvent (DMA:H2O = 2:1) were added to a reaction flask, and the reaction was carried out at 120 °C until the starting material disappeared. Saturated brine was added, and the mixture was extracted three times with ethyl acetate. The combined organic phases were dried and separated by column chromatography to give a white solid in 75% yield.

[0098] 1 H NMR(300MHz, CDCl3)δ8.37(d,J=6.9Hz,1H),7.66–7.60(m,1H),7.40(d,J=1.0Hz ,4H),7.33–7.26(m,1H),7.21–7.12(m,5H),6.92(d,J=6.1Hz,1H),4.93(s,2H). 13CNMR (75MHz, CDCl3) δ147.45,146.20,140.44,132.74,128.76,128.68,128.32,127.92,126 .30,126.11,126.06,124.82,121.18,117.70,113.15,107.42,51.93.HRMS(ESI)m / z:[M+H] + Calcd for C 21 H 16 F3N2O2S + 417.0880; Found 417.0881.

[0099] Example 13

[0100] Synthesized using 2-phenylimidazo[1,2-α]pyridine (1a) and sodium 2-thiophene sulfinate (2j) as raw materials (3j):

[0101]

[0102] 0.6 mmol of 2-phenylimidazo[1,2-α]pyridine (1a), 1.2 mmol of sodium 2-thiophene sulfinate (2j), 0.06 mmol of FeCl3, 1.5 mmol of potassium persulfate, and 3 mL of solvent (DMA:H2O = 2:1) were added to a reaction flask, and the reaction was carried out at 120 °C until the starting material disappeared. Saturated brine was added, and the mixture was extracted three times with ethyl acetate. The combined organic phases were dried and separated by column chromatography to give a white solid in 78% yield.

[0103] 1 H NMR (300MHz, CDCl3) δ8.41(d,J=6.9Hz,1H),7.69(d,J=9.1Hz,1H),7.57(dd,J=5.0 ,1.3Hz,1H),7.45–7.37(m,2H),7.37–7.27(m,5H),6.98–6.90(m,2H),4.99(s,2H). 13 CNMR (75MHz, CDCl3) δ147.91,146.12,138.00,135.41,135.07,132.98,128. 65,128.41,128.35,128.21,126.24,124.95,117.63,113.12,108.11,54.07.

[0104] Example 14

[0105] Synthesized using 2-phenylimidazo[1,2-α]pyridine (1a) and sodium 2-pyridinesulfinate (2k) as raw materials (3k):

[0106]

[0107] 0.6 mmol of 2-phenylimidazo[1,2-α]pyridine (1a), 1.2 mmol of sodium 2-pyridinesulfinate (2k), 0.06 mmol of FeCl3, 1.5 mmol of potassium persulfate, and 3 mL of solvent (DMA:H2O = 2:1) were added to a reaction flask, and the reaction was carried out at 120 °C until the starting material disappeared. Saturated brine was added, and the mixture was extracted three times with ethyl acetate. The combined organic phases were dried and separated by column chromatography to give a white solid in 70% yield.

[0108] 1 H NMR(300MHz, CDCl3)δ8.60–8.54(m,1H),8.45(dt,J=4.6,1.4Hz,1H),7.90–7.78( m,3H),7.67–7.60(m,2H),7.48–7.35(m,5H),7.05(t,J=6.9Hz,1H),5.23(s,2H). 13 CNMR (75MHz, CDCl3) δ156.10,150.38,147.67,146.20,137.96,133.05,128.72,1 28.59,128.37,127.81,126.25,125.00,122.90,117.57,113.07,107.15,48.81.

[0109] Example 15

[0110] Synthesized from 2-phenylimidazo[1,2-α]pyridine (1a) and sodium methyl sulfinate (2l):

[0111]

[0112] 0.6 mmol of 2-phenylimidazo[1,2-α]pyridine (1a), 0.9 mmol of sodium methanesulfonate (2l), 0.06 mmol of FeCl3, 1.5 mmol of potassium persulfate, and 3 mL of solvent (DMA:H2O = 2:1) were added to a reaction flask, and the reaction was carried out at 120 °C until the starting material disappeared. Saturated brine was added, and the mixture was extracted three times with ethyl acetate. The combined organic phases were dried and separated by column chromatography to give a white solid in 82% yield.

[0113] 1H NMR (300MHz, CDCl3) δ8.39(d,J=6.9Hz,1H),7.75(d,J=6.8Hz,2H),7.70(d,J=9.1Hz,1H),7.54–7.47 (m,2H),7.47–7.41(m,1H),7.36–7.30(m,1H),6.94(td,J=6.9,1.2Hz,1H),4.83(s,2H),2.63(s,3H). 13 CNMR (75MHz, CDCl3) δ147.44,146.46,133.54,129.29,128.87,128.53,126.30,124.94,117.82,113.19,108.02,50.95,39.61.

[0114] Example 16

[0115] Synthesized using 2-(4-bromophenyl)imidazo[1,2-α]pyridine (1e) and sodium phenylsulfinate (2b) as raw materials (3m):

[0116]

[0117] 0.6 mmol of 2-(4-bromophenyl)imidazo[1,2-α]pyridine (1e), 0.72 mmol of sodium phenylsulfinate (2b), 0.06 mmol of FeCl3, 1.5 mmol of potassium persulfate, and 3 mL of solvent (DMA:H2O = 2:1) were added to a reaction flask, and the reaction was carried out at 120 °C until the starting material disappeared. Saturated brine was added, and the mixture was extracted three times with ethyl acetate. The combined organic phases were dried and separated by column chromatography to give a white solid in 82% yield.

[0118] 1 H NMR(300MHz,Chloroform-d)δ8.36(d,J=7.0Hz,1H),7.63(d,J=9.0Hz,1H),7.52(td,J=7.0,1.4Hz,3H),7. 34(qd,J=7.5,6.7,2.0Hz,4H),7.23–7.12(m,3H),6.89(d,J=6.9Hz,1H),4.77(s,2H).HRMS(ESI)m / z:[M+H] + Calcd for C 20 H 16 BrN2O2S + 427.0111; Found 427.0111.

[0119] Example 17

[0120] Synthesized from 2-(4-bromophenyl)imidazo[1,2-α]pyridine (1e) and sodium p-tolylsulfinate (2a):

[0121]

[0122] 0.6 mmol of 2-(4-bromophenyl)imidazo[1,2-α]pyridine (1e), 0.9 mmol of sodium p-tolylsulfinate (2a), 0.06 mmol of FeCl3, 1.5 mmol of potassium persulfate, and 3 mL of solvent (DMA:H2O = 2:1) were added to a reaction flask, and the reaction was carried out at 120 °C until the starting material disappeared. Saturated brine was added, and the mixture was extracted three times with ethyl acetate. The combined organic phases were dried and separated by column chromatography to give a white solid in 84% yield.

[0123] 1 H NMR (300MHz, CDCl3) δ8.42(d,J=7.0Hz,1H),7.68(d,J=9.1Hz,1H),7.45–7.38(m,4H),7.37–7.31(m,1H ),7.24(d,J=8.5Hz,2H),7.12(d,J=7.7Hz,2H),6.95(td,J=6.9,1.2Hz,1H),4.82(s,2H),2.38(s,3H). 13 CNMR(75MHz, CDCl3)δ146.09,146.06,145.65,134.35,132.05,131.55,129.95, 129.78,128.25,126.39,124.93,122.53,117.58,113.20,108.48,52.64,21.76.

[0124] Example 18

[0125] Synthesized from 2-(4-bromophenyl)imidazo[1,2-α]pyridine (1e) and sodium p-bromophenyl sulfinate (2e) as raw materials (3o):

[0126]

[0127] 0.6 mmol of 2-(4-bromophenyl)imidazo[1,2-α]pyridine (1e), 1.2 mmol of sodium p-bromophenylsulfinate (2e), 0.06 mmol of FeCl3, 1.5 mmol of potassium persulfate, and 3 mL of solvent (DMA:H2O = 2:1) were added to a reaction flask, and the reaction was carried out at 120 °C until the starting material disappeared. Saturated brine was added, and the mixture was extracted three times with ethyl acetate. The combined organic phases were dried and separated by column chromatography to give a white solid in 75% yield.

[0128] 1 H NMR(300MHz, CDCl3)δ8.39(d,J=7.0Hz,1H),7.70–7.66(m,1H),7.50–7.44(m,2H),7.44–7.38(m,2H), 7.38–7.32(m,1H),7.30–7.26(m,2H),7.20(d,J=8.5Hz,2H),6.98(td,J=6.9,1.2Hz,1H),4.88(s,2H). 13 CNMR (75MHz, CDCl3) δ146.18,135.92,132.53,131.81,130.24,129.69,129.65 ,126.63,124.84,122.81,117.74,113.44,107.98,52.27.HRMS(ESI)m / z:[M+H] + Calcd for C 20 H 15 Br2N2O2S + 506.9195; Found 506.9196.

[0129] Example 19

[0130] Synthesized using 2-(4-bromophenyl)imidazo[1,2-α]pyridine (1e) and sodium cyclopropylsulfinate (2h) as starting materials (3p):

[0131]

[0132] 0.6 mmol of 2-(4-bromophenyl)imidazo[1,2-α]pyridine (1e), 0.9 mmol of sodium cyclopropyl sulfinate (2h), 0.06 mmol of FeCl3, 1.5 mmol of potassium persulfate, and 3 mL of solvent (DMA:H2O = 2:1) were added to a reaction flask, and the reaction was carried out at 120 °C until the starting material disappeared. Saturated brine was added, and the mixture was extracted three times with ethyl acetate. The combined organic phases were dried and separated by column chromatography to give a white solid in 74% yield.

[0133] 1 H NMR (300MHz, CDCl3) δ8.37(d,J=7.0Hz,1H),7.74–7.64(m,3H),7.64–7.57(m,2H),7.35–7.28(m,1H),6.93(td ,J=6.9,1.2Hz,1H),4.80(s,2H),2.24–2.17(m,1H),1.08(dt,J=6.6,3.3Hz,2H),0.81(tt,J=8.0,3.6Hz,2H). 13C NMR (75MHz, CDCl3) δ146.19,146.09,132.56,132.11,130.06,126.32,124.8 7,122.94,117.58,113.17,108.01,50.00,29.11,5.12.HRMS(ESI)m / z:[M+H] + Calcd for C 17 H 16 BrN2O2S + 391.0110, Found 391.0111.

[0134] Example 20

[0135] Synthesized using 2-(4-nitrophenyl)imidazo[1,2-α]pyridine (1f) and sodium p-tolylsulfinate (2a) as starting materials (3q):

[0136]

[0137] 0.6 mmol of 2-(4-nitrophenyl)imidazo[1,2-α]pyridine (1f), 0.9 mmol of sodium p-tolylsulfinate (2a), 0.06 mmol of FeCl3, 1.5 mmol of potassium persulfate, and 3 mL of solvent (DMA:H2O = 2:1) were added to a reaction flask, and the reaction was carried out at 120 °C until the starting material disappeared. Saturated brine was added, and the mixture was extracted three times with ethyl acetate. The combined organic phases were dried and separated by column chromatography to give a white solid in 75% yield.

[0138] 1 H NMR (300MHz, CDCl3) δ8.44(d,J=7.0Hz,1H),8.23–8.11(m,2H),7.74(d,J=9.1Hz,1H),7.69–7.63(m,2H),7.48(d ,J=8.3Hz,2H),7.43–7.37(m,1H),7.16(d,J=8.0Hz,2H),7.01(td,J=6.9,1.1Hz,1H),4.85(s,2H),2.38(s,3H). 13 C NMR (75MHz, CDCl3) δ147.47,146.35,145.95,144.83,139.70,134.42,130.14,128.98,128 .33,126.97,125.02,123.68,117.89,113.69,109.65,52.69,21.74.HRMS(ESI)m / z:[M+H] + Calcd forC 21 H18 N3O4S + 408.1013; Found 408.1013.

[0139] Example 21

[0140] Synthesized using 6-methyl-2-phenylimidazo[1,2-α]pyridine (1g) and sodium p-tolylsulfinate (2a) as raw materials (3r):

[0141]

[0142] 0.6 mmol of 6-methyl-2-phenylimidazo[1,2-α]pyridine (1 g), 0.9 mmol of sodium p-tolylsulfinate (2a), 0.06 mmol of FeCl3, 1.5 mmol of potassium persulfate, and 3 mL of solvent (DMA:H2O = 2:1) were reacted at 120 °C until the starting material disappeared. Saturated brine was added, and the mixture was extracted three times with ethyl acetate. The combined organic phases were dried and separated by column chromatography to give a white solid in 90% yield.

[0143] 1 H NMR (300MHz, CDCl3) δ8.12(s,1H),7.57(d,J=9.1Hz,1H),7.38(d,J=8.3Hz,2H),7.34–7.25(m ,5H),7.15(dd,J=9.2,1.4Hz,1H),7.07(d,J=8.1Hz,2H),4.86(s,2H),2.36(d,J=6.8Hz,6H). 13 C NMR (75MHz, CDCl3) δ147.19,145.32,145.04,134.35,133.19,129.85,129.15,128. 33,128.27,128.20,128.04,122.69,122.52,116.86,108.00,52.81,21.70,18.55.

[0144] Example 22

[0145] Synthesized using 7-bromo-2-phenylimidazo[1,2-α]pyridine (1h) and sodium p-tolylsulfinate (2a) as starting materials (3s):

[0146]

[0147] 0.6 mmol of 7-bromo-2-phenylimidazo[1,2-α]pyridine (1 h), 0.9 mmol of sodium p-toluenesulfinate (2 a), 0.06 mmol of FeCl3, 1.5 mmol of potassium persulfate, and 3 mL of solvent (DMA:H2O = 2:1) were added to a reaction flask, and the reaction was carried out at 120 °C until the starting material disappeared. Saturated brine was added, and the mixture was extracted three times with ethyl acetate. The combined organic phases were dried and separated by column chromatography to give a white solid in 80% yield.

[0148] 1 H NMR (300MHz, CDCl3) δ8.29(d,J=7.3Hz,1H),7.56(d,J=1.6Hz,1H),7.29–7.25(m,2H),7. 19(s,5H),6.99(d,J=8.1Hz,2H),6.79(dd,J=7.4,2.1Hz,1H),4.75(s,2H),2.26(s,3H). 13 C NMR (75MHz, CDCl3) δ147.98,145.65,145.45,134.01,132.63,132.41,129.86,128.37 ,128.12,128.05,125.50,116.17,114.46,108.75,52.39,21.64.HRMS(ESI)m / z:[M+H] + Calcd for C 21 H 18 BrN2O2S + 441.0267; Found 441.0267.

[0149] Example 23

[0150] Synthesized using 8-methyl-2-phenylimidazo[1,2-α]pyridine (1i) and sodium p-tolylsulfinate (2a) as raw materials (3t):

[0151]

[0152] 0.6 mmol of 8-methyl-2-phenylimidazo[1,2-α]pyridine (1i), 0.9 mmol of sodium p-tolylsulfinate (2a), 0.06 mmol of FeCl3, 1.5 mmol of potassium persulfate, and 3 mL of solvent (DMA:H2O = 2:1) were added to a reaction flask, and the reaction was carried out at 120 °C until the starting material disappeared. Saturated brine was added, and the mixture was extracted three times with ethyl acetate. The combined organic phases were dried and separated by column chromatography to give a white solid in 93% yield.

[0153] 1H NMR (300MHz, CDCl3) δ8.21(d,J=6.8Hz,1H),7.30(d,J=8.3Hz,2H),7.20(dt,J=9.6,2.8Hz ,5H),7.00(d,J=7.9Hz,3H),6.74(t,J=6.9Hz,1H),4.75(s,2H),2.56(s,3H),2.26(s,3H). 13 C NMR (75MHz, CDCl3) δ146.96,146.32,145.22,134.42,133.25,129.83,128.44,128. 31,128.19,127.99,127.44,124.82,122.74,112.91,108.61,52.85,21.68,17.18.

[0154] Example 24

[0155] Synthesized using 2-(2-thiophene)imidazo[1,2-α]pyridine (1j) and sodium p-tolylsulfinate (2a) as raw materials (3u):

[0156]

[0157] 0.6 mmol of 2-(2-thiophene)imidazo[1,2-α]pyridine (1j), 0.9 mmol of sodium p-toluenesulfinate (2a), 0.06 mmol of FeCl3, 1.5 mmol of potassium persulfate, and 3 mL of solvent (DMA:H2O = 2:1) were added to a reaction flask, and the reaction was carried out at 120 °C until the starting material disappeared. Saturated brine was added, and the mixture was extracted three times with ethyl acetate. The combined organic phases were dried and separated by column chromatography to give a white solid in 80% yield.

[0158] 1 H NMR (300MHz, CDCl3) δ8.72(d,J=6.7Hz,1H),8.60(s,1H),7.48(d,J=7.9Hz,2H),7.29(d,J=5. 2Hz,1H),7.15(d,J=7.9Hz,2H),7.07(d,J=3.2Hz,1H),6.94(s,2H),4.91(s,2H),2.33(s,3H). 13 C NMR (75MHz, CDCl3) δ151.32,148.80,145.86,142.92,135.04,134.03,132. 76,130.04,128.37,127.58,127.18,126.24,109.20,106.21,52.67,21.71.

[0159] Example 25

[0160] Synthesized using 2-(2-furan)imidazo[1,2-α]pyridine (1k) and sodium p-tolylsulfinate (2a) as starting materials (3v):

[0161]

[0162] 0.6 mmol of 2-(2-furan)imidazo[1,2-α]pyridine (1k), 0.9 mmol of sodium p-toluenesulfinate (2a), 0.06 mmol of FeCl3, 1.5 mmol of potassium persulfate, and 3 mL of solvent (DMA:H2O = 2:1) were added to a reaction flask, and the reaction was carried out at 120 °C until the starting material disappeared. Saturated brine was added, and the mixture was extracted three times with ethyl acetate. The combined organic phases were dried and separated by column chromatography to give a white solid in 82% yield.

[0163] 1 H NMR (300MHz, CDCl3) δ8.38(d,J=7.0Hz,1H),7.60(d,J=9.2Hz,1H),7.37(d,J=7.9Hz,2H),7.29(t,J=8.2Hz,1H),7.12(s ,1H),7.05(d,J=8.0Hz,2H),6.92(d,J=7.0Hz,1H),6.67(d,J=3.0Hz,1H),6.35–6.24(m,1H),5.07(s,2H),2.26(s,3H). 13 C NMR (75MHz, CDCl3) δ148.92,146.24,145.13,142.10,137.51,133.82,129.22,1 28.31,126.45,124.67,117.09,112.98,111.08,108.44,107.95,52.55,21.50.

[0164] Example 26

[0165] Synthesized using 2-tert-butylimidazo[1,2-α]pyridine (1l) and sodium p-tolylsulfinate (2a) as raw materials (3w):

[0166]

[0167] 0.6 mmol of 2-tert-butylimidazo[1,2-α]pyridine (1 L), 0.9 mmol of sodium p-tolylsulfinate (2 A), 0.06 mmol of FeCl3, 1.5 mmol of potassium persulfate, and 3 mL of solvent (DMA:H2O = 2:1) were added to a reaction flask, and the reaction was carried out at 120 °C until the starting material disappeared. Saturated brine was added, and the mixture was extracted three times with ethyl acetate. The combined organic phases were dried and separated by column chromatography to give a white solid in 86% yield.

[0168] 1 H NMR (300MHz, CDCl3) δ8.21(d,J=6.9Hz,1H),7.60(d,J=8.2Hz,3H),7.28(d,J=8.0Hz,2H),7. 20(t,J=8.1Hz,1H),6.76(t,J=6.9Hz,1H),4.89(s,2H),2.41(s,3H),1.30(d,J=2.1Hz,9H). 13 C NMR (75MHz, CDCl3) δ155.80,145.49,144.90,135.55,130.04,128.52,125.27,124.20,116.92,112.12,106.12,53.60,34.18,30.84,21.68.

[0169] Example 27

[0170] Synthesized from 6-phenyl-2,3-dihydroimidazole[2,1-b]thiazole (1m) and sodium p-tolylsulfinate (2a):

[0171]

[0172] 0.6 mmol of 6-phenyl-2,3-dihydroimidazole[2,1-b]thiazole (1m), 0.9 mmol of sodium p-toluenesulfinate (2a), 0.06 mmol of FeCl3, 1.5 mmol of potassium persulfate, and 3 mL of solvent (DMA:H2O = 2:1) were added to a reaction flask, and the reaction was carried out at 120 °C until the starting material disappeared. Saturated brine was added, and the mixture was extracted three times with ethyl acetate. The combined organic phases were dried and separated by column chromatography to give a white solid in 80% yield.

[0173] 1 H NMR (300MHz, CDCl3) δ7.40(d,J=7.8Hz,1H),7.06(d,J=8.1Hz,1H),4.45(s,1H),4.29(t,J=7.4Hz,1H),3.78(t,J=7.3Hz,1H). 13C NMR (75MHz, CDCl3) δ151.08,147.55,145.20,133.87,133.20,129.67,128.06,128.03,127.10,126.68,113.96,53.18,46.11,34.77,21.55.

[0174] Example 28

[0175] Synthesized using 6-phenylimidazolium[2,1-b]thiazole (1n) and sodium p-tolylsulfinate (2a) as raw materials (3y):

[0176]

[0177] 0.6 mmol of 6-phenylimidazolium[2,1-b]thiazole (1n), 0.9 mmol of sodium p-toluenesulfinate (2a), 0.06 mmol of FeCl3, 1.5 mmol of potassium persulfate, and 3 mL of solvent (DMA:H2O = 2:1) were added to a reaction flask, and the reaction was carried out at 120 °C until the starting material disappeared. Saturated brine was added, and the mixture was extracted three times with ethyl acetate. The combined organic phases were dried and separated by column chromatography to give a white solid in 78% yield.

[0178] 1 H NMR (300MHz, CDCl3) δ7.67(d,J=4.5Hz,1H),7.43(d,J=8.0Hz,2H),7.27–7.15( m,5H),7.12(d,J=7.9Hz,2H),6.86(d,J=4.4Hz,1H),4.69(s,2H),2.34(s,3H). 13 C NMR (75MHz, CDCl3) δ150.77,148.42,145.37,134.00,133.01,129.83,128.27,128 .16,127.78,127.49,119.07,112.72,109.77,77.58,77.16,76.74,53.45,21.62.

[0179] Example 29

[0180] Synthesized using 1-phenyl-3-methyl-5-amino-1H-pyrazole (1o) and sodium p-tolylsulfinate (2a) as raw materials (3z):

[0181]

[0182] 0.6 mmol of 1-phenyl-3-methyl-5-amino-1H-pyrazole (1o), 0.9 mmol of sodium p-tolylsulfinate (2a), 0.06 mmol of FeCl3, 1.5 mmol of potassium persulfate, and 3 mL of solvent (DMA:H2O = 2:1) were added to a reaction flask, and the reaction was carried out at 120 °C until the starting material disappeared. Saturated brine was added, and the mixture was extracted three times with ethyl acetate. The combined organic phases were dried and separated by column chromatography to give a white solid in 82% yield.

[0183] 1 H NMR (300MHz, CDCl3) δ7.65(d,J=8.3Hz,2H),7.50–7.42(m,4H),7.37–7.28(m,3H),4.40(br s,2H),4.12(s,2H),2.43(s,3H),1.62(s,3H). 13 C NMR (75MHz, CDCl3) δ148.75,145.56,144.99,138.05,134.66,129.78,129.58,128.54,127.61,124.01,90.17,53.08,21.65,11.24.

Claims

1. A method for synthesizing an arylmethyl sulfone compound, characterized in that, The chemical reaction formula of the synthesis method is as follows: Equation I In Formula I, Ar is selected from 2-phenylimidazo[1,2-α]pyridine, 2-(2-methylphenyl)imidazo[1,2-α]pyridine, 2-(3-methylphenyl)imidazo[1,2-α]pyridine, 2-(4-chlorophenyl)imidazo[1,2-α]pyridine, 2-(4-bromophenyl)imidazo[1,2-α]pyridine, 2-(4-nitrophenyl)imidazo[1,2-α]pyridine, 6-methyl- 2-Phenylidene imidazo[1,2-α]pyridine, 7-bromo-2-phenylimidazo[1,2-α]pyridine, 8-methyl-2-phenylimidazo[1,2-α]pyridine, 2-(thiophen-2-yl)imidazo[1,2-α]pyridine, 2-(furan-2-yl)imidazo[1,2-α]pyridine, 2-tert-butylimidazo[1,2-α]pyridine, 6-phenyl-2,3-dihydroimidazo[2,1- β ]thiazole, 6-phenylimidazole [2,1- β ]Thiazole, 1-phenyl-3-methyl-5-amino-1 H - One of the pyrazoles; R is selected from one of methyl, phenyl, p-tolyl, 4-fluorophenyl, 4-chlorophenyl, 4-bromophenyl, 4-methoxyphenyl, 2-chlorophenyl, cyclopropyl, p-trifluoromethylphenyl, thiophene-2-yl, and pyridin-2-yl. The reaction steps of the synthesis method are as follows: the raw material aromatic base compound Ar-H and sodium alkyl sulfinate RSO2Na, as well as the catalyst FeCl3 and oxidant K2S2O8, are added to a mixed system of DMA and water, and reacted at 110~130℃ until the raw material disappears. The mixture is then separated and purified to obtain aryl methyl sulfone compounds; the DMA is N,N-dimethylacetamide. The arylmethyl sulfone compounds specifically include the following compounds: 。 2. The method for synthesizing arylmethyl sulfone compounds according to claim 1, characterized in that, The molar ratio of the aromatic base, sodium alkyl sulfinate, catalyst, and oxidant is: .

3. The method for synthesizing arylmethyl sulfone compounds according to claim 2, characterized in that, In the DMA and water mixture, the volume ratio of DMA to water is 2:

1.

4. The method for synthesizing arylmethyl sulfone compounds according to claim 3, characterized in that, The reaction temperature is 120°C.

5. The method for synthesizing arylmethyl sulfone compounds according to claim 2, characterized in that, The concentration of the raw material aromatic base is 0.1~0.4 mol / L.

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