Preparation method of 5-sulfonyl-1,4-dihydropyridine compounds

Abstract

The present invention discloses a method for preparing a 5-sulfonyl-1,4-dihydropyridine compound, comprising the following steps: using an enaminone compound and an allene compound having structures such as those shown in formula (II) and formula (III) as raw materials, reacting in an organic solvent at 90 to 120° C. for 12 to 24 hours in the presence of an oxidant to obtain a reaction product, and then purifying the obtained reaction product to obtain a 5-sulfonyl-1,4-dihydropyridine compound shown in formula (I). The preparation method of the present invention has the characteristics of low cost, mild reaction conditions, simple operation, few reaction by-products, environmental protection, and high yield of the obtained target product, and therefore has broad application prospects.

Description

Technical Field

[0001] The present invention belongs to the technical field of organic compound synthesis, and particularly relates to a method for preparing 5-sulfonyl-1,4-dihydropyridine compounds. Background Art

[0002] Polysubstituted dihydropyridines (DHPs) are widely used as efficient photoredox agents and alkylation agents in organic synthesis. Therefore, the development of facile and efficient synthetic methods to prepare polyfunctional substituted dihydropyridine rings (skeletons) has attracted extensive attention.

[0003] Numerous methods for the synthesis of dihydropyridines have been reported. Among them, the Hantzsch reaction is particularly noteworthy due to its multicomponent, one-pot reaction and its ability to operate in water. However, this method also has drawbacks, such as long reaction times, demanding reaction conditions (refluxing acetic acid or alcohol), low to moderate product yields, and a limited substrate compatibility (suitable only for the synthesis of symmetric dihydropyridines). Summary of the Invention

[0004] In view of the problems existing in the above-mentioned prior art, the purpose of the present invention is to provide a method for preparing 5-sulfonyl-1,4-dihydropyridine compounds, which has the characteristics of mild reaction conditions, simple operation, atom economy, environmental friendliness and high yield.

[0005] In order to achieve the above object, the present invention adopts the following technical solutions:

[0006] The first aspect of the present invention provides a 5-sulfonyl-1,4-dihydropyridine compound, the structure of which is shown in the following formula (I):

[0007] (I)

[0008] Wherein, R is selected from any one of Ph, CH3-Ph, F-Ph, Cl-Ph, Br-Ph, OCH3, R 1 Any one selected from CH3, Bn, Ph, R 2 Selected from CH3 or CH3-Ph, R 3 Selected from H or CH3.

[0009] The second aspect of the present invention provides a method for preparing the above-mentioned 5-sulfonyl-1,4-dihydropyridine compound, comprising the following steps: using an enaminone compound and an allene compound represented by the following formula (II) and formula (III) as raw materials, reacting in an organic solvent at 90 to 120° C. for 12 to 24 hours in the presence of an oxidant to obtain a reaction product, and then purifying the obtained reaction product to obtain a 5-sulfonyl-1,4-dihydropyridine compound:

[0010] (II) (III)

[0011] Wherein, R is selected from any one of Ph, CH3-Ph, F-Ph, Cl-Ph, Br-Ph, OCH3, R 1 Any one selected from CH3, Bn, Ph, R 2 Selected from CH3 or CH3-Ph, R 3 Selected from H or CH3.

[0012] Preferably, the molar ratio of the oxidant, the enaminone compound, the allene compound and the oxidant is 1.2-3.0:1:1.2-2.0.

[0013] Preferably, the enaminone compound is selected from (Z)-3-(dimethylamino) -1-phenylpropyl-2-en-1-one, (Z)-3-(dimethylamino)-1-(o-tolyl)propylene glycol-2-en-1-one, (Z)-3-(dimethylamino)-1-(2-fluorophenyl)propyl-2-en-1-one, (Z)-3-(dimethylamino)-1-(m-tolyl)propylene glycol-2-en-1-one, (Z)-3-(dimethylamino)-1-(3-fluorophenyl)propyl-2-en-1-one, (Z)-3-(dimethylamino)-1-(p-tolyl)propylene glycol-2-en-1-one, (Z)-1-(4-bromophenyl)-3-(dimethylamino)propyl-2-en-1-one, (Z)-4-(dimethylamino)butyl-3-en-2-one, (Z)-3-(dimethylamino) -1-phenylpropyl-2-en-1-one.

[0014] Preferably, the oxidant is any one of divalent copper salt, silver salt, potassium persulfate, ammonium persulfate, potassium peroxymonosulfate, sodium percarbonate, and activated manganese dioxide; wherein the silver salt is silver acetate, silver carbonate, or silver trifluoroacetate.

[0015] Preferably, the organic solvent is one or a combination of two or more of ethylene glycol dimethyl ether, acetonitrile, dichloromethane, dichloroethane, chloroform, chlorobenzene, and 1,4-dioxane.

[0016] Preferably, the allene compound is selected from N,4-dimethyl-N-(prop-1,2-dien-1-yl)benzenesulfonamide, 4-methyl-N-phenyl-N-(prop-1,2-dien-1-yl)benzenesulfonamide, N-benzyl-4-methyl-N-(prop-1,2-dien-1-yl)benzenesulfonamide, and N-methyl-N-(prop-1,2-dien-1-yl)methylsulfonamide.

[0017] Preferably, the reaction product is purified by thin layer chromatography, and the developing solvent system used is petroleum ether / ethyl acetate, and the volume ratio of petroleum ether to ethyl acetate in the developing solvent system is 1:0.2-0.5.

[0018] Compared with the prior art, the present invention has the following beneficial effects:

[0019] This invention uses enaminones and allenes as raw materials, and prepares 5-sulfonyl-1,4-dihydropyridine compounds through a one-step cyclization reaction in the presence of an oxidant. This preparation method features mild reaction conditions, simple operation, few reaction byproducts, environmental friendliness, and a high yield of the target product. Enaminones, one of the main raw materials, are simple to synthesize, have high conversion rates, and have a wide range of substrate applications. Furthermore, the allenes and oxidants used are low-cost. Due to their widespread distribution among biologically and pharmaceutically active molecules, 5-sulfonyl-1,4-dihydropyridine compounds have broad application prospects. BRIEF DESCRIPTION OF THE DRAWINGS

[0020] In order to more clearly illustrate the technical solutions in the embodiments of the present invention, the following briefly introduces the drawings required for use in 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 paying any creative work.

[0021] Figure 1 The synthetic route of 5-sulfonyl-1,4-dihydropyridine compounds is shown below;

[0022] Figure 2 is the NMR spectrum of compound 3a prepared in Example 1;

[0023] Figure 3 This is the carbon spectrum of compound 3a prepared in Example 1. DETAILED DESCRIPTION

[0024] In the following description, specific details such as specific system structures and technologies are provided for illustration rather than limitation to facilitate a thorough understanding of the embodiments of the present invention. However, it should be clear to those skilled in the art that the present invention may also be implemented in other embodiments without these specific details.

[0025] Example 1

[0026] Reference Figure 1 , prepare 5-sulfonyl-1,4-dihydropyridine compounds, specifically compound 3a, whose structural formula is shown below:

[0027] (3a)

[0028] Specific steps: Ethylene glycol dimethyl ether, (Z)-3-(dimethylamino)-1-phenylpropyl-2-en-1-one (0.20 mmol, 0.035 g), N,4-dimethyl-N-(prop-1,2-dien-1-yl)benzenesulfonamide (0.30 mmol, 0.067 g), and sodium percarbonate (0.3 mmol, 0.047 g) were added to a 10 mL Shrek tube in sequence. The mixture was stirred in a sealed environment at 100°C for 24 h. After the reaction was completed, thin layer chromatography (developing solvent system: petroleum ether / ethyl acetate, volume ratio of 1:0.5) was used to separate and purify the product. The product was a yellow solid, namely compound 3a, with a yield of 88%. Its NMR and C spectroscopy results are shown as follows: Figure 2 and Figure 3 shown. 1 H NMR (400 MHz, CDCl3)δ 7.77 (d, J = 7.6 Hz, 2H), 7.47-7.42 (m, 3H),7.39 (t, J = 7.7 Hz, 2H), 7.33 (d, J = 8.0 Hz, 2H), 7.01 (s, 1H), 6.57 (s, 1H), 3.23 (s, 2H), 3.09 (s, 3H), 2.43 (s, 3H). 13 C NMR (101 MHz, CDCl3)δ 194.25,144.78, 144.38, 139.21, 136.87, 135.91, 130.96, 130.06, 128.55, 128.46,128.27, 115.79, 113.42, 41.73, 21.83, 20.88.

[0029] Example 2

[0030] Preparation of 5-sulfonyl-1,4-dihydropyridine compounds, specifically compound 3b, whose structural formula is shown below:

[0031] (3b)

[0032] Specific steps: Ethylene glycol dimethyl ether, (Z)-3-(dimethylamino)-1-(o-tolyl)propylene glycol-2-en-1-one (0.20 mmol, 0.038 g), N,4-dimethyl-N-(prop-1,2-dien-1-yl)benzenesulfonamide (0.30 mmol, 0.067 g), and copper acetate (0.30 mmol, 0.060 g) were added sequentially to a 10 mL Shrek tube. The mixture was stirred at 100°C in a sealed environment for 20 h. After the reaction was completed, thin-layer chromatography (TLC) was used as the developing solvent: petroleum ether / ethyl acetate, with a volume ratio of 1:0.5. The product was obtained as compound 3b as an orange solid with a yield of 85%. 1 H NMR (400 MHz, CDCl3)δ7.81 – 7.76 (m, 1H), 7.35 (d, J = 8.5 Hz, 1H), 7.31 – 7.27 (m, 1H), 7.22 – 7.13(m, 1H), 7.07 (s, 1H), 7.00 (s, 1H), 6.35 (s, 1H), 3.24 (s, 1H), 3.05 (s,1H), 2.46 – 2.44 (m, 1H), 2.21 (s, 1H). 13 C NMR (101 MHz, CDCl3)δ 195.94,145.10, 144.45, 139.09, 136.75, 135.87, 135.79, 130.99, 130.10, 129.48,128.33, 127.37, 125.40, 116.25, 114.65, 41.71, 21.88, 20.42, 19.57.

[0033] Example 3

[0034] Preparation of 5-sulfonyl-1,4-dihydropyridine compounds, specifically compound 3c, whose structural formula is shown below:

[0035] (3c)

[0036] Specific steps: Dichloroethane, (Z)-3-(dimethylamino)-1-(2-fluorophenyl)propyl-2-en-1-one (0.20 mmol, 0.039 g), N,4-dimethyl-N-(prop-1,2-dien-1-yl)benzenesulfonamide (0.30 mmol, 0.067 g), and potassium peroxymonosulfate (0.3 mmol, 0.057 g) were added sequentially to a 10 mL Shrek tube. The mixture was stirred at 90°C in a sealed environment for 3 h. After completion of the reaction, thin-layer chromatography (developing solvent: petroleum ether / ethyl acetate, volume ratio of 1:0.5) was used to separate and purify the product. The product was compound 3c as an orange solid with a yield of 85%. 1 H NMR (400 MHz, CDCl3)δ7.77 (d, J = 8.0 Hz, 2H), 7.43-7.37 (m, 1H), 7.34 (d, J = 8.0 Hz, 1H), 7.28-7.24(m, 1H), 7.17 (dt, J = 7.5, 0.9 Hz, 1H), 7.07 (dd, J = 13.2, 4.7 Hz, 1H), 7.00(s, 1H), 6.45 (s, 1H), 3.23 (s, 2H), 3.09 (s, 3H), 2.44 (s, 3H). 13 C NMR (101MHz, CDCl3)δ 189.96, 159.1(d, J = 249.7 Hz), 145.45, 144.50, 136.68, 135.62,131.87 (d, J = 7.9 Hz), 130.08, 129.93, 128.27, 124.48, 116.51, 116.31 (d, J =21.9 Hz), 114.23, 41.81, 21.85, 20.51.

[0037] Example 4

[0038] Preparation of 5-sulfonyl-1,4-dihydropyridine compounds, specifically compound 3d, whose structural formula is shown below:

[0039] (3d)

[0040] The specific steps are as follows: dichloromethane, (Z)-3-(dimethylamino)-1-(m-tolyl)propylene glycol-2-en-1-one (0.20 mmol, 0.038 g), N,4-dimethyl-N-(prop-1,2-dien-1-yl)benzenesulfonamide (0.30 mmol, 0.067 g), and potassium peroxymonosulfate (0.4 mmol, 0.076 g) were added sequentially to a 10 mL Shrek tube. The mixture was stirred at 100°C in a sealed environment for 18 h. After completion of the reaction, thin-layer chromatography (developing solvent: petroleum ether / ethyl acetate, volume ratio of 1:0.5) was used to separate and purify the product. The product was obtained as a yellow solid, compound 3d, with a yield of 79%. 1 H NMR (400 MHz, CDCl3)δ 7.78 (d, J = 8.1 Hz, 2H), 7.33 (d, J = 8.1 Hz, 2H), 7.29 – 7.23 (m, 3H), 7.23 – 7.17 (m, 1H), 7.02 (s, 1H), 6.58 (s, 1H), 3.23 (s, 2H), 3.09 (s, 3H), 2.43 (s, 3H), 2.36 (s, 3H). 13 C NMR (101 MHz, CDCl3)δ 194.49, 144.74, 144.33,139.19, 138.48, 136.91, 135.84, 131.66, 130.01, 128.93, 128.25, 128.21,125.50, 115.60, 113.38, 41.70, 21.81, 21.57, 20.81.

[0041] Example 5

[0042] Preparation of 5-sulfonyl-1,4-dihydropyridine compounds, specifically compound 3e, whose structural formula is shown below:

[0043] (3e)

[0044] Specific steps: Ethylene glycol dimethyl ether, (Z)-3-(dimethylamino)-1-(3-fluorophenyl)propyl-2-en-1-one (0.20 mmol, 0.039 g), N,4-dimethyl-N-(prop-1,2-dien-1-yl)benzenesulfonamide (0.30 mmol, 0.067 g), and ammonium persulfate (0.3 mmol, 0.0684 g) were added sequentially to a 10 mL Shrek tube. The mixture was stirred at 120°C in a sealed environment for 12 h. After completion of the reaction, thin-layer chromatography (developing solvent: petroleum ether / ethyl acetate, volume ratio of 1:0.2) was used to separate and purify the product. The product was compound 3e as an orange solid with a yield of 71%. 1 H NMR (400 MHz, CDCl3)δ 7.76 (d, J = 8.3 Hz, 2H), 7.35 (ddd, J = 14.0, 8.7, 4.3 Hz, 3H), 7.21(dt, J = 7.5, 1.1 Hz, 1H), 7.17-7.10 (m, 2H), 7.01 (d, J = 0.8 Hz, 1H), 6.57 (d, J = 0.7 Hz, 1H), 3.21 (s, 2H), 3.11 (s, 3H), 2.43 (s, 3H). 13 C NMR (101 MHz, CDCl3)δ 192.57 (d, J = 2.1 Hz), 163.83, 161.36, 145.06, 144.47, 141.20 (d, J =6.4 Hz), 136.73, 135.72, 130.42,129.97, 128.26, 124.11 (d, J = 3.1 Hz),118.02, 117.80, 116.13, 115.57, 115.35, 113.02, 41.81, 21.83, 20.79.

[0045] Example 6

[0046] Preparation of 5-sulfonyl-1,4-dihydropyridine compounds, specifically compound 3f, whose structural formula is shown below:

[0047] (3f)

[0048] Specific steps: Chloroform, (Z)-3-(dimethylamino)-1-(p-tolyl)propylene glycol-2-en-1-one (0.20 mmol, 0.038 g), N,4-dimethyl-N-(prop-1,2-dien-1-yl)benzenesulfonamide (0.30 mmol, 0.067 g), and ammonium persulfate (0.48 mmol, 0.11 g) were added sequentially to a 10 mL Shrek tube. The mixture was stirred at 90°C in a sealed environment for 24 h. After completion of the reaction, thin-layer chromatography (developing solvent: petroleum ether / ethyl acetate, volume ratio of 1:0.5) was used to separate and purify the product. The product was compound 3f as an orange solid with a yield of 76%. 1 H NMR (400 MHz, CDCl3)δ 7.76(d, J = 8.2 Hz, 2H), 7.34 (dd, J = 12.5, 8.1 Hz, 4H), 7.18 (d, J = 7.9 Hz, 2H), 7.01 (s, 1H), 6.58 (s, 1H), 3.22 (s, 2H), 3.08 (s, 3H), 2.42 (s, 3H), 2.37(s, 3H). 13 C NMR (101 MHz, CDCl3)δ 194.92, 144.26, 141.02, 137.09, 135.82,129.96, 128.10, 115.03, 114.02, 41.63, 24.75, 21.78, 20.37.

[0049] Example 7

[0050] Prepare 5-sulfonyl-1,4-dihydropyridine compounds, specifically compound 3g, whose structural formula is shown below:

[0051] (3g)

[0052] Specific steps: acetonitrile, (Z)-1-(4-bromophenyl)-3-(dimethylamino)propyl-2-en-1-one (0.20 mmol, 0.051 g), N,4-dimethyl-N-(prop-1,2-dien-1-yl)benzenesulfonamide (0.30 mmol, 0.067 g), and ammonium persulfate (0.24 mmol, 0.055 g) were added sequentially to a 10 mL Shrek tube, and the mixture was stirred at 90° C. in a sealed environment for 20 h. After the reaction was completed, thin layer chromatography (developing solvent system: petroleum ether / ethyl acetate, volume ratio of the two: 1:0.5) was used to separate and purify the product. The product was 3 g of an orange solid compound with a yield of 71%.1 H NMR (400 MHz, CDCl3)δ 7.76(d, J = 8.2 Hz, 2H), 7.53 (d, J = 8.3 Hz, 2H), 7.32 (t, J = 7.3 Hz, 4H), 7.01 (s,1H), 6.54 (s, 1H), 3.21 (s, 2H), 3.11 (s, 3H), 2.43 (s, 3H). 13 C NMR (101 MHz, CDCl3)δ 192.97, 144.82, 144.46, 137.91, 136.73, 135.75, 131.80, 130.07,130.06, 128.26, 125.54, 116.07, 113.20, 41.79, 21.84, 20.84.

[0053] Example 8

[0054] Preparation of 5-sulfonyl-1,4-dihydropyridine compounds, specifically compound 3h, whose structural formula is shown below:

[0055] (3 hours)

[0056] Specific steps: dichloromethane, (Z)-4-(dimethylamino)butyl-3-en-2-one (0.20 mmol, 0.023 g), N,4-dimethyl-N-(prop-1,2-dien-1-yl)benzenesulfonamide (0.30 mmol, 0.067 g), and ammonium persulfate (0.48 mmol, 0.11 g) were added sequentially to a 10 mL Shrek tube, and the mixture was stirred at 110°C in a sealed environment for 15 h. After the reaction was completed, thin layer chromatography (developing solvent system: petroleum ether / ethyl acetate, volume ratio of 1:0.5) was used to separate and purify the product. The product was an orange solid compound 3h, and the yield was 79%. 1 H NMR (400 MHz, CDCl3)δ 7.72 (d, J = 8.0Hz, 2H), 7.29 (d, J = 7.9 Hz, 2H), 6.98 (s, 1H), 6.79 (s, 1H), 3.16 (s, 3H), 3.02 (s, 2H), 2.40 (s, 3H), 2.15 (s, 3H). 13CNMR (101 MHz, CDCl3)δ 194.91,144.29, 140.93, 137.08, 135.88, 130.00, 128.17, 115.20, 114.13, 41.66, 24.79,21.82, 20.44.

[0057] Example 9

[0058] Preparation of 5-sulfonyl-1,4-dihydropyridine compounds, specifically compound 3i, whose structural formula is as follows:

[0059] (3i)

[0060] Specific steps: 1,4-dioxane, (Z)-3-(dimethylamino)-1-phenylpropyl-2-en-1-one (0.20 mmol, 0.035 g), N,4-dimethyl-N-(prop-1,2-dien-1-yl)benzenesulfonamide (0.30 mmol, 0.067 g), and sodium percarbonate (0.3 mmol, 0.047 g) were added sequentially to a 10 mL Shrek tube. The mixture was stirred at 110°C in a sealed environment for 18 h. After completion of the reaction, thin-layer chromatography (developing solvent: petroleum ether / ethyl acetate, volume ratio of 1:0.35) was used to separate and purify the product. The product was compound 3i as an orange solid with a yield of 73%. 1 H NMR (500 MHz, CDCl3)δ 7.80(d, J = 7.8 Hz, 2H), 7.44 (d, J = 7.6 Hz, 3H), 7.37 (t, J = 7.4 Hz, 2H), 7.31 (d, J =7.8 Hz, 2H), 7.16 (s, 1H), 6.60 (s, 1H), 3.85 (q, J = 6.4 Hz, 1H), 3.18 (s,3H), 2.42 (s, 3H), 1.08 (d, J = 6.4 Hz, 3H). 13 C NMR (126 MHz, CDCl3)δ 194.13,144.19, 143.39, 139.56, 137.98, 137.80, 130.99, 130.05, 128.45, 128.43,128.03, 119.88, 118.82, 41.96, 26.19, 23.38, 21.83.

[0061] Example 10

[0062] Preparation of 5-sulfonyl-1,4-dihydropyridine compounds, specifically compound 3j, whose structural formula is as follows:

[0063] (3j)

[0064] Specific steps: Dichloromethane, (Z)-3-(dimethylamino)-1-phenylpropyl-2-en-1-one (0.20 mmol, 0.062 g), 4-methyl-N-phenyl-N-(prop-1,2-dien-1-yl)benzenesulfonamide (0.4 mmol, 0.114 g), and ammonium persulfate (0.6 mmol, 0.137 g) were added sequentially to a 10 mL Shrek tube. The mixture was stirred at 120°C in a sealed environment for 12 hours. After completion of the reaction, the product was isolated and purified by thin-layer chromatography (developing solvent: petroleum ether / ethyl acetate, volume ratio: 1:0.35). The product was obtained as an orange solid, Compound 3j, in a yield of 75%. 1 H NMR (400 MHz, CDCl3)δ 7.82(d, J = 8.3 Hz, 2H), 7.51 (dd, J = 6.7, 1.5 Hz, 3H), 7.48 – 7.45 (m, 1H), 7.42 –7.35 (m, 6H), 7.29 – 7.24 (m, 1H), 7.13 – 7.08 (m, 3H), 3.37 (s, 2H), 2.45(s, 3H). 13 C NMR (101 MHz, CDCl3)δ 194.62, 144.61, 142.74, 142.09, 138.77,135.55, 134.78, 131.32, 130.25, 130.12, 128.65, 128.54, 128.37, 127.06,120.94, 118.01, 115.10, 21.85, 21.38.

[0065] Example 11

[0066] Preparation of 5-sulfonyl-1,4-dihydropyridine compounds, specifically compound 3k, whose structural formula is as follows:

[0067] (3k)

[0068] Specific steps: 1,4-dioxane, (Z)-3-(dimethylamino)-1-phenylpropyl-2-en-1-one (0.20 mmol, 0.035 g), N-benzyl-4-methyl-N-(prop-1,2-dien-1-yl)benzenesulfonamide (0.30 mmol, 0.090 g), and activated manganese dioxide (0.4 mmol, 0.0248 g) were added sequentially to a 10 mL Shrek tube. The mixture was stirred at 100°C in a sealed environment for 20 hours. After completion of the reaction, the product was isolated and purified by thin-layer chromatography (developing solvent: petroleum ether / ethyl acetate, volume ratio: 1:0.2). The product was obtained as a yellow solid, compound 3k, in an 82% yield. 1 H NMR (400 MHz, CDCl3)δ7.47-7.43 (m, 3H), 7.40-7.35 (m, 5H), 7.19-7.17 (m, 2H), 6.98 (d, J = 1.2 Hz,1H), 6.75 (t, J = 0.8 Hz, 1H), 4.42 (s, 2H), 3.55 (s, 2H), 2.93 (s, 2H). 13 C NMR(101 MHz, CDCl3)δ 194.23, 144.21, 138.83, 137.38, 135.27, 131.29, 129.56,128.96, 128.66, 128.59, 127.52, 115.02, 113.55, 58.34, 40.11, 21.75.

[0069] The present invention is not limited to the above-mentioned specific implementation methods. Various changes made by ordinary technicians in this field based on the above-mentioned concept without creative work are all within the scope of protection of the present invention.

Claims

1. A method for preparing a 5-sulfonyl-1,4-dihydropyridine compound, characterized in that: The following steps are involved: Using enaminone compounds and allene compounds represented by the following formulas (II) and (III) as raw materials, reacting in an organic solvent at 90-120° C. for 12-24 hours in the presence of an oxidant to obtain a reaction product, which is then purified to obtain a 5-sulfonyl-1,4-dihydropyridine compound represented by the following formula (I): （Ⅰ） （Ⅱ） （Ⅲ） Wherein, R is selected from any one of -Ph, CH3-Ph-, F-Ph-, Cl-Ph-, Br-Ph-, and -OCH3, and R 1 Any one selected from -CH3, -Bn, -Ph, R 2 Selected from -CH3 or CH3-Ph-, R 3 Selected from H or -CH3; The oxidant is any one of silver salt, potassium persulfate, ammonium persulfate, potassium peroxymonosulfate, sodium percarbonate, and activated manganese dioxide; The organic solvent is one or a combination of two or more of ethylene glycol dimethyl ether, acetonitrile, dichloromethane, dichloroethane, chloroform, chlorobenzene, and 1,4-dioxane.

2. The method for preparing 5-sulfonyl-1,4-dihydropyridine compounds according to claim 1, characterized in that: The molar ratio of the oxidant, the enaminone compound and the allene compound is 1.2-3.0:1:1.2-2.

0.

3. The method for preparing 5-sulfonyl-1,4-dihydropyridine compounds according to claim 1, characterized in that: The enaminones are selected from the group consisting of (Z)-3-(dimethylamino)-1-phenylpropyl-2-en-1-one, (Z)-3-(dimethylamino)-1-(o-tolyl)propylene glycol-2-en-1-one, (Z)-3-(dimethylamino)-1-(2-fluorophenyl)propyl-2-en-1-one, (Z)-3-(dimethylamino)-1-(m-tolyl)propylene glycol-2-en-1-one, (Z)-3-(dimethylamino)-1-(3-fluorophenyl)propyl-2-en-1-one, (Z)-3-(dimethylamino)-1-(p-tolyl)propylene glycol-2-en-1-one, (Z)-1-(4-bromophenyl)-3-(dimethylamino)propyl-2-en-1-one, (Z)-4-(dimethylamino)-1-(2-fluorophenyl)propyl-2-en-1-one. Any one of butyl-3-en-2-one and (Z)-3-(dimethylamino)-1-phenylpropyl-2-en-1-one.

4. The method for preparing 5-sulfonyl-1,4-dihydropyridine compounds according to claim 1, characterized in that: The allene compound is selected from N,4-dimethyl-N-(prop-1,2-dien-1-yl)benzenesulfonamide, 4-methyl-N-phenyl-N-(prop-1,2-dien-1-yl)benzenesulfonamide, N-benzyl-4-methyl-N-(prop-1,2-dien-1-yl)benzenesulfonamide, and N-methyl-N-(prop-1,2-dien-1-yl)methylsulfonamide.

5. The method for preparing 5-sulfonyl-1,4-dihydropyridine compounds according to claim 1, characterized in that: The reaction product is purified by thin layer chromatography, and the developing solvent system used is petroleum ether / ethyl acetate, and the volume ratio of petroleum ether to ethyl acetate in the developing solvent system is 1:0.2-0.5.

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