Process for the synthesis of alpha-hydroxy amides or 3,3-disubstituted oxindoles

Abstract

The application discloses a green and environment-friendly reaction of visible light-induced alpha, beta-unsaturated amide and aryl triazene in air without any additive or cosolvent, so that bifunctionalization is realized, and when the condition is changed and when there is a protective group on N, a cyclization reaction can also be realized. The metal-free reaction has high chemical selectivity, and corresponding beta-hydroxyl compounds and competitive cyclization products can be synthesized. The reaction has considerable advantages, including high selectivity, mild reaction condition, cleanness, no need of transition metal catalyst, high atom economy and good functional group compatibility.

Description

Technical Field

[0001] This invention belongs to the field of compound synthesis technology, specifically relating to a visible light-induced arylation and hydroxylation reaction of α,β-unsaturated amides (III) using arylacrylamide compound (I) and aryltriazene (II) as substrates, under room temperature conditions and with ultraviolet light as the light source, to synthesize α-hydroxyamide products (III), and the synthesis of 3,3-disubstituted indole-2-one compounds (VI) using blue light as the light source and with the addition of photosensitizers and promoters. This reaction has significant advantages, including mild and clean reaction conditions, no need for transition metal catalysts, high atom economy, good selectivity, and good functional group compatibility. Background Technology

[0002] Alpha-hydroxyamides and their derivatives are widely found in natural products and drug molecules, forming the core skeletons of some antitumor drugs and antibacterial compounds. The natural product (+)-avimycin was first isolated from marine-derived fungi in 2006 (Wohlfahrt, M.; Harms, K.; Koert, U., European Journal of Organic Chemistry 2012, 2260-2265). Verucopeptin inhibitors can reduce the expression of target genes and exhibit antitumor activity against drug-resistant cancer cells, and are commonly used in cancer-related research (Andler, O.; Kazmaier, U., Org Lett. 2022, 24, 2541-2545). PDHK is also a type of inhibitor that plays an important role in controlling glucose homeostasis. (Aicher, TD; Anderson, RC; Gao, JP; Shetty, SS; Coppola, GM; Stanton, JL; Knorr, DC; Sperbeck, DM; Brand, LJ; Vinluan, CC; Kaplan, EL; Dragland, CJ; Tomaselli, HC; Islam, A.; Lozito, RJ; Liu, XL; Manila, WM; Fillers, WS; Del Grande, D.; Walter, RE; Mann, WR, J. Med. Chem. 2000, 43, 236-249).

[0003] In the past decade, research on constructing indolone skeletons using N-aryl-substituted acrylamides as substrates through radical addition and cyclization reactions has attracted widespread attention. Due to the unique chemical structure of N-arylacrylamides, which can rapidly cyclize via radical initiation without polymerization, they have become ideal substrates for the synthesis of 3,3-disubstituted indol-2-ones via radical addition / cyclization reactions. Traditional methods for synthesizing aryl hydroxylated and cyclized oxidized indoles (Kindt S, Wicht K, Heinrich M R. Angew Chem Int Ed, 2016, 55(30): 8744-8751. Wang J, Xue L, Hong M, et al. Green Chem., 2020, 22(2): 411-416. Fu W, Xu F, Fu Y, et al. J. Org. Chem., 2013, 78(23): 12202-12206. Chen M, Xing X, X. Wang X, Ren Z and Guan Z. Org. Chem. Front., 2022, 9, 5557-5563. Tang S, Zhou Dand Wang C, Eur. J. Org. Chem., 2014, 3656-3661. Zhang Q, Wang S, Huang X, Wang J (and Pan Y, Tetrahedron Lett., 2015, 56, 2512-2516.) In contrast, we used aryltriazenes as the aryl source. Synthetically, aryltriazenes are ideal aryl sources for radical cascade reactions, exhibiting superior reactivity, good stability, and diverse transformation characteristics compared to traditional arylating agents such as diazonium salts. The construction of traditional aryl-hydroxylated compounds is often carried out under heating and high-energy xenon lamp irradiation. However, we achieved aryl-hydroxylation reactions under mild conditions without any photosensitizers or oxidants, and selectively synthesized 3,3-disubstituted indole oxides under different conditions. Summary of the Invention

[0004] To address the shortcomings of existing technologies, the present invention aims to provide a method for synthesizing α-hydroxyamide compounds and 3,3-disubstituted indole-2-ones. The hydroxyl groups in this method are derived from inexpensive air, and the substrates are also inexpensive and readily available. This invention does not require transition metal catalysts or equivalent amounts of chemical oxidants. The reaction process is green, environmentally friendly, safe, and energy-efficient, with mild reaction conditions, a wide range of applicable substrates, good functional group compatibility of the products, readily available raw materials, simple operation, and high regioselectivity.

[0005] The synthetic reaction of this invention includes the following steps:

[0006] One objective of this invention is to provide a method for synthesizing compounds containing α-hydroxyamides, using arylacrylamide (I) and aryltriazene (II) as raw materials, and reacting them under conditions of visible light source in air atmosphere and room temperature. After the reaction, the products are separated and characterized by conventional separation and purification methods to obtain α-hydroxyamide compounds and di- to 3,3-disubstituted indole compounds under the conditions of adding photosensitizer and B(C6F5)3 (tris(C6F5)3) ...) (tris(C6F5)3) (tris(C6F5)3) (tris(C6F5)3)) (tris(C6F5)3) (tris(C6F5)3)) (tris(C6F5)3) (tris(C6F5)3)) (tris(C6F5)3) (tris(C6F5)3)) (tris(C6F5)3) (tris(C6F5)3

[0007] The structural formula 1 of the compound containing the α-hydroxyamide skeleton is as follows:

[0008]

[0009] Substituent R1 is one or more of phenyl, naphthyl, substituted aryl, etc.; the number of substituents is 1 to 5, preferably 1 or 2; the substituents in the substituted aryl group are one or more of fluorine, chlorine, bromine, iodine, phenyl, methoxy, ethoxy, aryl, ethyl, tert-butyl, etc.

[0010] Substituent R2 is one or more of phenyl, naphthyl, and substituted aryl; the substituent in the substituted aryl group is one or more of fluorine, chlorine, bromine, iodine, phenyl, methoxy, ethoxy, aryl, ethyl, and tert-butyl; the number of substituents is 1 to 5, preferably 1 or 2;

[0011] Substituent R3 is one or more of phenyl, tert-butyl, bromine, chlorine, iodine, and nitro; the substituent in the substituted aryl group is one or more of the following; the number of substituents is 1-2, preferably 1;

[0012] Substituent R4 is at least one of methyl, n-butyl, ethyl, phenyl, and benzyl.

[0013] The synthetic route for preparing compounds containing an α-hydroxyamide skeleton is as follows:

[0014]

[0015] The R substituents are the same as those described above.

[0016] Furthermore, the light source is any one of blue light, violet light (390nm-435nm), white light, green light, and red light, preferably violet light (390nm-395nm).

[0017] Further, the reaction solvent is one of dimethyl sulfoxide, ethanol, N,N-dimethylacetamide, dichloromethane, dichloroethane, acetonitrile, methanol, acetonitrile and water (2:1), preferably a mixed solvent of acetonitrile and water.

[0018] Furthermore, the molar concentration of the reacting aryltriazine is either 0.16M or 0.17M, preferably 0.17M.

[0019] Furthermore, the reaction time is 36 hours.

[0020] The synthetic route for the preparation of 3,3-disubstituted indole compounds is as follows:

[0021]

[0022] The R substituents are the same as those described above.

[0023] Furthermore, the light source is any one of blue light, violet light (390nm-465nm), white light, green light, and red light, preferably blue light (460-465nm).

[0024] Furthermore, the reaction solvent is one or more of acetonitrile, ethanol, and methanol, preferably methanol.

[0025] Furthermore, the molar concentration of the reacting aryltriazine is either 0.1M or 0.2M, preferably 0.2M.

[0026] Further, the additive is B(C6F5)3, preferably B(C6F5)3; its concentration in the solvent is 0.005-0.02M, preferably 0.02M;

[0027] Furthermore, the photosensitizer is disodium eosin Y, preferably disodium eosin Y; the concentration of the photosensitizer in the solvent is 0.005-0.02M, preferably 0.01M;

[0028] Furthermore, the reaction time is 24 hours.

[0029] The beneficial effects of this invention are:

[0030] This invention utilizes the different substituents attached to the N-ring of α,β-unsaturated amides and the control of conditions to selectively synthesize compounds with α-hydroxyamide skeletons or 3,3-disubstituted indole oxides with aryltriazene. By changing the substituents attached to the N-ring of arylacrylamide and the different groups attached to the benzene ring of aryltriazene, a series of compounds with different structures containing α-hydroxyamide skeletons and 3,3-disubstituted indole oxides were efficiently prepared. The preparation method of this invention is carried out at room temperature and pressure, without the need for additional catalysts, oxidants, or inert gas protection, and the operation and post-processing are simple. The reaction of this invention utilizes light, a clean energy source, with mild conditions, energy saving and environmental protection, inexpensive and readily available raw materials, simple operation, safety and reliability, and can be prepared in large quantities with high product yields. Detailed Implementation

[0031] The following examples will help to further understand the present invention, but the scope of the invention is not limited thereto. The processes, conditions, reagents, experimental methods, etc., used to implement the present invention, except as specifically mentioned below, are all common knowledge and general knowledge in the art, and the present invention does not have any particular limitations. The data given in the following examples include specific operations, reaction conditions, and products. Product purity was identified by NMR and high-resolution mass spectrometry.

[0032] Synthesis of aryltriazene:

[0033]

[0034] According to previous literature reports (Sutar SM, Kalkhambkar R G. Chemistry Select, 2021, 6(25): 6548-6556), the specific steps are as follows: Add ArNH2 (10 mmol) to a 100 mL round-bottom flask and cool it in an ice bath (0-5℃). Then, slowly add concentrated HCl (2 mL of concentrated hydrochloric acid with a mass concentration of 36-38) at 0℃. Prepare an aqueous solution of NaNO2 (11 mmol) (5 mL) and slowly add it dropwise to the hydrochloric acid solution of the amine. Continue stirring the obtained diazonium salt solution in an ice bath for 15 minutes. Then, add the above diazonium salt solution to a mixture containing K2CO3 (1.2 mol / L) and secondary amine (10 mmol) in one go in an ice bath. Continue stirring the reaction solution at room temperature for about 30 minutes. After the reaction is detected by thin-layer chromatography, filter and recrystallize the crude product with ethanol (or it can be purified by column chromatography) to obtain the pure product.

[0035] In the above amine structural formula, the substituent R2 is one or more of phenyl, naphthyl, and substituted aryl; the substituted aryl is substituted phenyl and / or substituted naphthyl, and the substituent in the substituted aryl is fluorine, chlorine, bromine, iodine, nitro, methoxy, ethoxy, aryl, ethyl, tert-butyl, or 3,5-dimethyl, and the corresponding products are obtained in sequence.

[0036] Synthesis of N-arylallylamide:

[0037]

[0038] N-Arylallylamide was synthesized according to the method described in the reference (Dai YY, Cui M, Li XQ, et al. New J. Chem., 2023, 47(12): 5780-5785.). Amine (5 mmol) and DCM (dichloromethane) (20 mL) were added to a 100 mL round-bottom flask equipped with a stir bar. The reaction mixture was cooled to 0 °C, and then methacryloyl chloride (6 mmol) and Et3N (6 mmol) were added. The mixture was stirred at room temperature for 2 h. 5 mL of saturated brine was added, and the mixture was extracted three times with DCM. The combined extracts were dried over MgSO4. The mixture was filtered and evaporated under vacuum. Following these steps, the corresponding NH allylamide was obtained. The product was purified by column chromatography on silica gel using PE (petroleum ether) / EA (ethyl acetate) (volume ratio, 20:11) as the eluent.

[0039] In the above amine structural formula, substituent R1 is a substituted aryl, phenyl, and / or naphthyl group, and the number of substituents on the substituted aryl group is 1-5, preferably 1 or 2; the substituents in the substituted aryl group are fluorine, chlorine, bromine, iodine, methoxy, aryl, nitro, or 3,5-dimethyl, and the corresponding products are obtained sequentially. Synthesis of N-methyl-N-arylallylamide:

[0040]

[0041] The synthesis of N-methyl-N-arylallylamide was carried out according to the method described in the reference (Dai YY, Cui M, Li XQ, et al. New J. Chem., 2023, 47(12): 5780-5785.). The specific steps are as follows: Add the above-mentioned NH allylamide and THF (tetrahydrofuran) (20 mL) to a 100 mL round-bottom flask equipped with a stir bar. Cool the mixture to 0 °C, and then add NaH (sodium hydride) (7.5 mmol). Stir the mixture at room temperature for 40 minutes. Then add MeI (methane iodide) (7.5 mmol) to the above solution and stir for another 3 hours. Pour the mixture into saturated brine and extract three times with EtOAc (ethyl acetate). Dry the combined extracts with MgSO4 (anhydrous magnesium sulfate), filter, and purify by chromatography on silica gel with PE / EA (20:1) as the eluent to obtain the corresponding N-methyl-N-arylallylamide.

[0042] In the above amine structural formula, R3 is specifically phenyl, tert-butyl, bromine, chlorine, iodine or nitro, respectively, and the corresponding N-methyl-N-arylallylic amide products are obtained in turn.

[0043] The process and conditions are the same as above, except that N,N-diphenylmethylacrylamide, N-ethyl-N-phenylmethylacrylamide, N-butyl-N-phenylmethylacrylamide, or N-benzyl-N-phenylmethylacrylamide can also be obtained by replacing iodomethane with other alkylating agents such as iodobenzene, iodoethane, n-iodobutane, or benzyl bromide in turn.

[0044] Example 1

[0045]

[0046] In a dry, clean 25 mL transparent quartz tube (used as a photoreactor), reaction substrate (1a) (0.2 mmol, 35.0 mg) and compound (2a) (0.5 mmol, 2.5 equiv., 97.5 mg) were added sequentially, followed by the addition of solvent CH3CN / H2O (volume ratio, 2:1, 3 mL). The reaction was then irradiated with ultraviolet light (390-395 nm) for 36 h. Post-treatment was as follows: After the reaction was complete, 5 mL of water was added to quench the reaction mixture, and the aqueous mixture was extracted with ethyl acetate (3 × 5 mL, repeated 3 times, 5 mL each time). After extraction, the organic phase was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The purified solid 3a (40.5 mg, yield 72%) was obtained by column chromatography (eluent: petroleum ether / ethyl acetate 30:1-10:1, v / v, (10:1 in this case)). The parameters of the product obtained by nuclear magnetic resonance (NMR) and high-resolution mass spectrometry (HMS) were as follows: 2-hydroxy-2-methyl-N,3-di-p-tolylpropionamide (3a): a new compound. (Eluent: petroleum ether (60-90℃) / EtOAc=10:1, v / v). 40.5 mg, yield: 72%, yellow solid. mp: 133.4-135.3℃. 1 H NMR (400MHz, CDCl3) δ8.38 (s, 1H), 7.41-7.37 (dt, J = 8.4, 2.6Hz, 2H), 7.14-7.09 (m, 7H) ,3.41(d,J=13.6Hz,1H),2.84(d,J=13.6Hz,1H),2.31(s,6H),2.21(s,1H),1.53(s,3H). 13 C NMR(100MHz, CDCl3)δ173.4,137.1,135.1,134.1,132.5,130.3,129.6,120.0,76.5,45.3,26.6,21.2,21.0.HRMS(ESI)m / z Calcd for C 18 H 21 NO2[M+H] +:284.1645; Found:284.1640.

[0047] Example 2

[0048] The reaction steps and operations were the same as in Example 1, except that the reaction was carried out without ultraviolet light irradiation. The reaction was stopped, and the target product 3a was not obtained after post-treatment. This indicates that the reaction cannot proceed without light.

[0049] Example 3

[0050] The reaction procedure and operation were the same as in Example 1, except that the reaction was carried out under a nitrogen atmosphere. The reaction was stopped, and after post-treatment, the target product 3a (11.5 mg, yield 21%) was obtained. The product formation under a nitrogen atmosphere is likely due to the presence of a small amount of oxygen in the solvent. This result indicates that the absence of air or oxygen is detrimental to the reaction.

[0051] Example 4

[0052] The reaction procedure and operation were the same as in Example 1, except that the reaction was carried out under ultraviolet light irradiation using an equal volume of acetonitrile:water (1:1) as the solvent. The reaction was stopped, and after post-treatment, the target product 3a (28.9 mg, yield 51%) was obtained, indicating a decrease in yield under these conditions.

[0053] Example 5

[0054] The reaction procedure and operation were the same as in Example 1, except that an equal volume of tetrahydrofuran was used as the solvent instead of CH3CN / H2O. The reaction was stopped, and post-processing yielded only the trace target product 3a. This result indicates that the conditions were unfavorable for the reaction.

[0055] Example 6

[0056] The reaction procedure and operation were the same as in Example 1, except that compound (2a) (0.2 mmol, 1 equiv., 37.9 mg) was added to initiate the reaction. The reaction was stopped, and the target product 3a (23.8 mg, yield 42%) was obtained after post-treatment.

[0057] Example 7

[0058]

[0059] The reaction procedure and operation were the same as in Example 1, except that the reactant 1b (32.2 mg, 0.2 mmol) was added to the reaction system instead of the substrate (1a). The reaction was stopped after 48 h of irradiation with ultraviolet light (390-395 nm). Post-processing yielded the target product 3b (27.0 mg, yield 50%) as a white solid. The parameters of the product were determined by nuclear magnetic resonance (NMR) and high-resolution mass spectrometry (HMS): 2-hydroxy-2-methyl-N,3-di-p-tolylpropionamide (3b): new compound. (Eluent: petroleum ether (60-90 °C) / EtOAc = 10:1, v / v). 27.0 mg, yield: 50%, white solid. mp: 125.1-127.8 °C. 1 H NMR (600MHz, CDCl3) δ8.49 (s, 1H), 7.51 (d, J = 7.9Hz, 2H), 7.32 (t, J = 7.4Hz, 2H), 7.14-7.08 (m ,5H),3.40(d,J=13.7Hz,1H),2.86(d,J=13.7Hz,1H),2.37(s,1H),2.31(s,3H),1.54(s,3H). 13 C NMR(150MHz, CDCl3)δ173.6,137.5,137.1,132.4,130.3,129.6,129.1,124.5,119.9,76.5,45.2,26.6,21.2.HRMS(ESI)m / z Calcd for C 17 H 19 NO2[M+H] + :270.1489; Found:270.1486.

[0060] Example 8

[0061]

[0062] The reaction procedure and operation were the same as in Example 1, except that the reactant 1c (47.4 mg, 0.2 mmol) was added to the reaction system instead of the substrate (1a). The reaction was stopped, and after post-treatment, the target product 3c (39.1 mg, yield 57%) was obtained as a white solid. The parameters of the product obtained were as follows: N-([1,1'-biphenyl]-4-yl)-2-hydroxy-2-methyl-3-(p-tolyl)acrylamide (3c): new compound. (Eluent: petroleum ether (60-90℃) / EtOAc=10:1, v / v). 39.1 mg, yield: 57%, white solid.mp: 129.6-131.3℃.1 H NMR (600MHz, CDCl3) δ8.55(s,1H),7.60-7.53(m,6H),7.42(t,J=7.5Hz,2H),7.32(t,J=7.4Hz,1H),7.14(d,J =8.1Hz,2H),7.11(d,J=8.0Hz,2H),3.41(d,J=13.7Hz,1H),2.86(d,J=13.7Hz,1H),2.31(s,3H),1.55(s,3H). 13 CNMR (150MHz, CDCl3) δ173.6,140.6,137.4,137.1,136.8,132.4,130.3,129 .6,128.9,127.7,127.2,127.0,120.2,76.6,45.2,26.6,21.2.HRMS(ESI)m / z Calcd for C 23 H 23 NO2[M+H] + :346.1807; Found:346.1811.

[0063] Example 9

[0064]

[0065] The reaction procedure and operation were the same as in Example 1, except that the reactant added to the reaction system was 1d (38.4 mg, 0.2 mmol) instead of the reaction substrate (1a), and the reaction was carried out under ultraviolet light (390-395 nm) for 48 h. The reaction was stopped, and after post-processing, the target product 3d (32.7 mg, yield 55%) was obtained as a yellow solid. The parameters of the product were determined by nuclear magnetic resonance (NMR) and high-resolution mass spectrometry: 2-hydroxy-N-(4-methoxyphenyl)-2-methyl-3-(p-tolyl)acrylamide (3d): novel compound. (Eluent: petroleum ether (60-90 °C) / EtOAc = 10:1, v / v). 32.7 mg, yield: 55%. Yellow solid, mp: 96.1-97.2 °C. 1 H NMR (600MHz, CDCl3) δ8.36 (s, 1H), 7.41 (d, J = 8.9Hz, 2H), 7.12 (dd, J = 8.3, 10.1Hz, 4H), 6.85 (d, J = 8.9Hz, 2H),3.79(s,3H),3.40(d,J=13.7Hz,1H),2.84(d,J=13.7Hz,1H),2.31(s,3H),2.28(s,1H),1.53(s,3H). 13C NMR (150MHz, CDCl3) δ173.33,156.54,137.01,132.52,130.68,130.30,129.51,121.66,114.20,76.43,55.58,45.25,26.53,21.17.HRMS (ESI) m / z Calcd for C 18 H 21 NO3[M+H] + :300.1600; Found 300.1598.

[0066] Example 10

[0067]

[0068] The reaction procedure and operation were the same as in Example 1, except that the reactant 1e (35.8 mg, 0.2 mmol) was used instead of the substrate (1a) in the reaction system. The reaction was stopped after 48 h of irradiation with ultraviolet light (390-395 nm). Post-processing yielded the yellow solid target product 3e (25.7 mg, yield 45%). The parameters of the product were determined by NMR and high-resolution mass spectrometry: N-(4-fluorophenyl)-2-hydroxy-2-methyl-3-(p-tolyl)acrylamide (3e): new compound. (Eluent: petroleum ether (60-90℃) / EtOAc = 10:1, v / v). 25.7 mg, yield: 45%, white solid.mp: 104.7.6-106.1℃. 1 H NMR (600MHz, CDCl3) δ8.46 (s, 1H), 7.44-7.46 (m, 2H), 7.12 (s, 4H), 7.00 (t, J = 8.4Hz, 2H) ,3.38(d,J=13.7Hz,1H),2.85(d,J=13.7Hz,1H),2.39(s,1H),2.31(s,3H),1.53(s,3H). 13 C NMR(150MHz,CDCl3)δ173.5,160.3(d,J CF =241.6Hz), 137.2, 133.5 (d, J) CF =3.2Hz),132.3,130.3,129.6,121.7(d,J CF =7.6Hz), 115.7(d,J) CF =22.6Hz),76.5,45.2,3.6,21.2.HRMS(ESI)m / z Calcd for:C 17 H18 FNO2[M+H] + :288.1400; Found:288.1403.

[0069] Example 11

[0070]

[0071] The reaction procedure and operation were the same as in Example 1, except that the reactant 1f (35.8 mg, 0.2 mmol) was added to the reaction system instead of the substrate (1a). The reaction was stopped after 48 h of irradiation with ultraviolet light (390-395 nm). Post-processing yielded the yellow solid target product 3f (27 mg, yield 47%). The parameters of the product were determined by NMR and high-resolution mass spectrometry: N-(3-fluorophenyl)-2-hydroxy-2-methyl-3-(p-tolyl)acrylamide (3f): new compound. (Eluent: petroleum ether (60-90 °C) / EtOAc = 10:1, v / v). 27.0 mg, yield: 47%, white solid.mp: 105.5-107.1 °C. 1 H NMR (600MHz, CDCl3) δ8.54(s,1H),7.51(d,J=8.8Hz,1H),7.26-7.22(m,1H),7.11(d,J=4.4Hz,5H),6.80(td ,J=8.3,2.3Hz,1H),3.39(d,J=13.7Hz,1H),2.85(d,J=13.7Hz,1H),2.31(s,3H),2.29(s,1H),1.53(s,3H). 13 C NMR(150MHz,CDCl3)δ173.7,163.1(d,J CF =243.0Hz),139.1,139.0,137.3,132.2,130.3,130.1(d,J CF =9.0Hz)129.7,115.2(d,J CF =1.6Hz), 111.2(d,J CF =21.0Hz), 107.3(d,J) CF =27.0Hz),76.6,45.2,26.5,21.2.HRMS(ESI)m / z Calcd for C 17 H 18 FNO2[M+H] + :288.1400; Found:288.1398.

[0072] Example 12

[0073]

[0074] The reaction procedure and operation were the same as in Example 1, except that 1 g (47.8 mg, 0.2 mmol) of the starting material was added to the reaction system to replace the reaction substrate (1a), and the reaction was carried out under ultraviolet light (390-395 nm) for 48 h. The reaction was stopped, and after post-processing, 3 g (31.3 mg, yield 44%) of the white solid target product was obtained. The parameters of the obtained product were detected by nuclear magnetic resonance and high-resolution mass spectrometry: N-(4-bromophenyl)-2-hydroxy-2-methyl-3-(p-tolyl)acrylamide (3 g): new compound. (Eluent: petroleum ether (60-90℃) / EtOAc=10:1, v / v). 31.3 mg, yield: 44%, white solid.mp: 115.6-116.9℃. 1 H NMR (600MHz, CDCl3) δ8.48(s,1H),7.42(s,4H),7.11(s,4H),3.38(d,J=13.6Hz,1H),2.84(d,J=13.8Hz,1H),2.31(s,3H),2.25(s,1H),1.53(s,3H). 13 CNMR(150MHz, CDCl3)δ173.6,137.2,136.6,132.2,132.0,130.3,129.6,121.5,117.1,76.6,45.2,26.5,21.2.HRMS(ESI)m / z Calcd for C 17 H 18 BrNO2[M+H] + :348.0594; Found:348.0597.

[0075] Example 13

[0076]

[0077] The reaction procedure and operation were the same as in Example 1, except that the starting material added to the reaction system was 1h (47.8 mg, 0.2 mmol) to replace the reaction substrate (1a), and the reaction was carried out under ultraviolet light (390-395 nm) for 48 h. The reaction was stopped, and after post-treatment, the white solid target product 3h (38.2 mg, yield 55%) was obtained. The parameters of the obtained product were detected by nuclear magnetic resonance and high-resolution mass spectrometry: N-(3-bromophenyl)-2-hydroxy-2-methyl-3-(p-tolyl)acrylamide (3h) novel compound. (Eluent: petroleum ether (60-90℃) / EtOAc = 10:1, v / v). 38.2 mg, yield: 55%, white solid.mp: 107.7-108.9℃. 1 H NMR (600MHz, CDCl3) δ8.49(s,1H),7.79(s,1H),7.40(d,J=7.8Hz,1H),7.23(d,J=7.6Hz,1H),7.16(t, J=7.8Hz,1H),7.11(s,4H),3.37(d,J=13.7Hz,1H),2.84(d,J=13.7Hz,1H),2.32(s,3H),1.53(s,3H). 13 C NMR (150MHz, CDCl3) δ173.7,138.8,137.3,132.2,130.4,130.3,129.7,127.5,122.8,122.7,118.3,76.6,45.2,26.53,21.2.HRMS(ESI)m / z Calcd for C 17 H 18 BrNO2[M+H] + :348.0594; Found:348.0598.

[0078] Example 14

[0079]

[0080] The reaction procedure and operation were the same as in Example 1, except that the reactant added to the reaction system was 1i (42.2 mg, 0.2 mmol) instead of the reaction substrate (1a). The reaction was stopped, and after post-processing, the target product 3i (38.1 mg, yield 60%) was obtained as a brown solid. The parameters of the product were determined by nuclear magnetic resonance and high-resolution mass spectrometry: 2-hydroxy-2-methyl-N-(2-naphthyl)-3-(p-tolyl)propionamide (3i): new compound. (Eluent: petroleum ether (60-90℃) / EtOAc = 10:1, v / v). 38.1 mg, yield: 60%, white solid.mp: 96.1-97.8℃. 1 H NMR (600MHz, CDCl3) δ8.95(s,1H),7.94(d,J=7.5Hz,1H),7.80(d,J=8.1Hz,1H),7.64(d,J=8.2Hz,1H),7.45-7.42(m,3H),7.37(t,J=8.04H z,1H),7.16(d,J=7.9Hz,2H),7.08(d,J=7.8Hz,2H),3.40(d,J=13.7Hz,1H),2.88(d,J=13.7Hz,1H),2.84(s,1H),2.29(s,3H),1.60(s,3H). 13 C NMR (150MHz, CDCl3) δ174.0,136.9,134.1,132.6,132.0,130.3,129.5,128.7,127. 0,126.1,126.0,150.8,150.6,120.7,120.1,77.0,45.5,26.8,21.2.HRMS(ESI)m / z Calcd for C 21 H 21 NO2[M+H] + :320.1651; Found:320.1650.

[0081] Example 15

[0082]

[0083] The reaction procedure and operation were the same as in Example 1, except that the reactant 1j (37.8 mg, 0.2 mmol) was added to the reaction system to replace the substrate (1a), and the reaction was carried out under ultraviolet light (390-395 nm) for 48 h. The reaction was stopped, and after post-processing, the target product 3j (30.5 mg, yield 51%) was obtained as a yellow solid. The parameters of the obtained product were detected by nuclear magnetic resonance and high-resolution mass spectrometry: N-(3,5-dimethylphenyl)-2-hydroxy-2-methyl-3-(p-tolyl)acrylamide (3j): new compound. (Eluent: petroleum ether (60-90℃) / EtOAc=10:1, v / v). 30.5 mg, yield: 51%, yellow solid. mp: 97.1-98.8℃. 1 H NMR (600MHz, CDCl3) δ8.41(s,1H),7.16(s,2H),7.14(d,J=8.1Hz,2H),7.11(d,J=8.2Hz,2H),6.7 6(s,1H),3.39(d,J=13.7Hz,1H),2.85(d,J=13.7Hz,1H),2.32(s,3H),2.29(s,6H),1.53(s,3H). 13 C NMR(150MHz, CDCl3)δ173.5,138.8,137.4,137.0,132.5,130.3,129.6,126.2,117.6,76.5,45.2,26.6,21.5,21.2.HRMS(ESI)m / z Calcd for C 19 H 23 NO2[M+H] + :298.1802; Found:298.1798.

[0084] Example 16

[0085]

[0086] The reaction procedure and operation were the same as in Example 1, except that the reactant 2b (87.5 mg, 0.5 mmol) was used instead of the substrate (2a) in the reaction system. The reaction was stopped after 48 h of irradiation with ultraviolet light (390-395 nm). Post-processing yielded the white solid target product 3k (35.3 mg, yield 66%). Nuclear magnetic resonance (NMR) and high-resolution mass spectrometry (HMS) were used to detect the parameters of the product: 2-hydroxy-2-methyl-3-phenyl-N-(p-tolyl)propionamide (3k): new compound. (Eluent: petroleum ether (60-90 °C) / EtOAc = 10:1, v / v). 35.3 mg, yield: 66%, white solid.mp: 112.6-113.3 °C. 1 H NMR(400MHz, CDCl3)δ8.38(s,1H),7.37(dt,J=8.4,2.8Hz,2H),7.32-7.27(m,3H),7.25-7.22(m,2H),7.1 1(d,J=8.2Hz,2H),3.42(d,J=13.6Hz,1H),2.89(d,J=13.6Hz,1H),2.31(s,3H),2.24(s,1H),1.54(s,3H). 13 C NMR(100MHz, CDCl3)δ173.3,135.7,134.9,134.2,130.5,129.6,128.8,127.4,76.5,45.7,26.6,21.0.HRMS(ESI)m / zCalcd for C 17 H 19 NO2[M+K] + :308.1047; Found:308.1042.

[0087] Example 17

[0088]

[0089] The reaction procedure and operation were the same as in Example 1, except that the starting material added to the reaction system was 2c (116.1 mg, 0.5 mmol), replacing compound (2a). The reaction was stopped, and after post-treatment, the target product 3l (37.2 mg, yield 57%) was obtained as a white solid. The parameters of the product obtained were as follows: 3-(4-tert-butylphenyl)-2-hydroxy-2-methyl-N-(p-tolyl)propionamide (3l): new compound. (Eluent: petroleum ether (60-90℃) / EtOAc = 10:1, v / v). 37.2 mg, yield: 57%. White solid. mp.: 127.5-128.3℃. 1 H NMR (400MHz, CDCl3) δ8.40(s,1H),7.38(d,J=8.4Hz,2H),7.32(d,J=8.4Hz,2H),7.17(d,J=8.4Hz,2H),7.12(d,J =8.8Hz,2H),3.39(d,J=13.6Hz,1H),2.87(d,J=13.6Hz,1H),2.34(s,1H),2.32(s,3H),1.54(s,3H),1.30(s,9H). 13 C NMR (100MHz, CDCl3) δ173.6,150.2,135.0,134.1,132.6,130.2,129.5,150.67,120.1,76.5,45.2,34.6,31.4,26.5,21.0.HRMS(ESI)m / z Calcd for C 21 H 27 NO2[M+Na] + :348.1934; Found:348.1939.

[0090] Example 18

[0091]

[0092] The reaction procedure and operation were the same as in Example 1, except that the starting material added to the reaction system was 2d (102.5 mg, 0.5 mmol), replacing compound (2a). The reaction was stopped, and after post-treatment, the target product 3m (45.2 mg, yield 75%) was obtained as a white solid. The parameters of the product were determined by nuclear magnetic resonance (NMR) and high-resolution mass spectrometry (HMS): 2-hydroxy-3-(4-methoxyphenyl)-2-methyl-N-(p-tolyl)propionamide (3m): new compound. (Eluent: petroleum ether (60-90℃) / EtOAc = 10:1, v / v). 45.2 mg, yield: 76%, white solid.mp: 127.3-129.1℃. 1 HNMR (400MHz, CDCl3) δ8.39(s,1H),7.38(dt,J=8.4 2.5Hz,2H),7.16(dt,J=8.8 3.0Hz,2H),7.11(d,J=9.4Hz,2H),6.83(dt,J=8.8 3.0Hz,1H),3.77(s,3H),3.38(d,J=13.7Hz,1H),2.81(d,J=13.8Hz,1H),2.31(s,3H),2.27(s,1H),1.53(s,3H). 13 C NMR(100MHz, CDCl3)δ173.4,159.0,135.0,134.1,131.5,129.6,127.5,120.0,114.3,76.6,55.4,44.9,26.5,21.0.HRMS(ESI)m / z Calcd for C 18 H 21 NO3[M+H] + :300.1594; Found:300.1590.

[0093] Example 19

[0094]

[0095] The reaction procedure and operation were the same as in Example 1, except that the starting material added to the reaction system was 2e (150.5 mg, 0.5 mmol) to replace compound (2a). The reaction was stopped, and after post-treatment, the target product 3n (42.9 mg, yield 62%) was obtained as a white solid. The parameters of the product obtained were as follows: 3-([1,1'-biphenyl]-4-yl)-2-hydroxy-2-methyl-N-(p-tolyl)propionamide (3n): new compound. (Eluent: petroleum ether (60-90℃) / EtOAc = 10:1, v / v). 42.9 mg, yield: 62%, white solid.mp: 136.1-137.2℃. 1 H NMR(400MHz, CDCl3)δ8.43(s,1H),7.58-7.52(m,4H),7.45-7.41(m,2H),7.40-7.37(m,2H),7.36-7.31(m,3H) ,7.12(d,J=8.2Hz,2H),3.46(d,J=13.6Hz,1H),2.94(d,J=13.6Hz,1H),2.38(s,1H),2.31(s,3H),1.58(s,3H). 13 C NMR (100MHz, CDCl3) δ173.3,140.8,140.3,134.9,134.7,134.2,130.9,129. 6,128.9,127.5,127.5,127.1,120.0,76.6,45.4,26.7,21.0.HRMS(ESI)m / z Calcd for C 23 H 23 NO2[M+H] + :346.1802;Found:346.1803。

[0096] Example 20

[0097]

[0098] The reaction procedure and operation were the same as in Example 1, except that the starting material added to the reaction system was 2f (150.5 mg, 0.5 mmol) replacing compound (2a). The reaction was stopped after 48 h of irradiation with ultraviolet light (390-395 nm), and post-processing yielded the target product 3o (37.8 mg, yield 55%), a brown solid. The parameters of the product obtained were as follows: 3-([1,1'-biphenyl]-2-yl)-2-hydroxy-2-methyl-N-(p-tolyl)propionamide (3o): new compound. (Eluent: petroleum ether (60-90℃) / EtOAc = 10:1, v / v). 37.8 mg, yield: 55%, brown solid.mp: 151.1-152.9℃. 1 H NMR (600MHz, CDCl3) δ8.31 (s, 1H), 7.42 (t, J = 7.6Hz, 2H), 7.32-7.37 (m, 6H), 7.28-7.23 (m, 3H), 7.09 (d ,J=8.2Hz,2H),3.35(d,J=14.2Hz,1H),3.23(d,J=14.1Hz,1H),2.30(s,3H),2.08(s,1H),1.28(s,3H). 13 C NMR (150MHz, CDCl3) δ173.3,143.4,141.7,135.0,134.0,133.3,131.2,130.7,129. 8,129.5,128.6,127.7,127.4,127.2,119.9,77.2,41.3,26.9,21.0.HRMS(ESI)m / z Calcd for C 23 H 23 NO2[M+H] + Found: 346.1807; Found: 346.1805.

[0099] Example 21

[0100]

[0101] The reaction procedure and operation were the same as in Example 1, except that the starting material added to the reaction system was 2j (101.5 mg, 0.5 mmol) replacing compound (2a). The reaction was stopped after 48 h of irradiation with ultraviolet light (390-395 nm), and post-processing yielded the target product 3p (30.0 mg, yield 50%) as a yellow solid. The parameters of the product obtained were as follows: 3-(4-ethylphenyl)-2-hydroxy-2-methyl-N-(p-tolyl)acrylamide (3p): new compound. (Eluent: petroleum ether (60-90℃) / EtOAc = 10:1, v / v). 30 mg, yield: 50%, yellow solid. mp: 117.6-118.8℃. 1 H NMR (600MHz, CDCl3) δ8.43 (s, 1H), 7.36 (d, J = 7.6Hz, 2H), 7.16-7.08 (m, 6H), 3.36 (d, J = 13.7Hz, 1H), 2.8 5(d,J=13.7Hz,1H),2.64(s,1H),2.60(q,J=7.6Hz,2H),2.30(s,3H),1.52(s,3H),1.20(t,J=7.6Hz,3H). 13 C NMR(100MHz, CDCl3)δ173.5,143.3,134.9,134.1,132.8,130.4,129.5,128.3,120.0,76.4,45.3,28.5,26.5,21.0,15.6.HRMS(ESI)m / zCalcd for C 19 H 23 NO2[M+H] + Found: 298.1802; Found: 298.1804.

[0102] Example 22

[0103]

[0104] The reaction procedure and operation were the same as in Example 1, except that the starting material added to the reaction system was 2h (109.5 mg, 0.5 mmol) as a substitute for compound (2a). The reaction was stopped, and after post-treatment, the target product 3q (37.6 mg, 60% yield) was obtained as a yellow solid. The parameters of the product obtained were as follows: 3-(4-ethoxyphenyl)-2-hydroxy-2-methyl-N-(p-tolyl)propionamide (3q): new compound. (Eluent: petroleum ether (60-90℃) / EtOAc = 10:1, v / v). 37.6 mg, yield: 60%, yellow solid. mp: 105.1-106.3℃. 1 H NMR (600MHz, CDCl3) δ8.41(s,1H),7.37(d,J=8.3Hz,2H),7.14(d,J=8.5Hz,2H),7.10(d,J=8.2Hz,2H),6.81(d,J=8.5Hz,2H),3.98(q, J=7.0Hz,2H),3.36(d,J=13.8Hz,1H),2.80(d,J=13.8Hz,1H),2.32(d,J=5.1Hz,1H),2.30(s,3H),1.52(s,3H),1.38(t,J=7.0Hz,3H). 13 C NMR (150MHz, CDCl3) δ173.5,158.4,135.0,134.1,131.4,129.5,127.4,120.0,114.8,76.5,63.5,44.8,26.5,21.0,14.9.HRMS(ESI)m / z Calcd for C 19 H 23 NO3[M+H] + :314.1756; Found:314.1753.

[0105] Example 23

[0106]

[0107] The reaction procedure and operation were the same as in Example 1, except that the starting material added to the reaction system was 2i (112.5 mg, 0.5 mmol) to replace compound (2a). The reaction was stopped after 48 h of irradiation with ultraviolet light (390-395 nm), and post-processing yielded the target product 3r (43.0 mg, yield 67%), a brown solid. The parameters of the product obtained were as follows: 2-hydroxy-2-methyl-3-(2-naphthyl)-N-(p-tolyl)acrylamide (3r): new compound. (Eluent: petroleum ether (60-90℃) / EtOAc = 10:1, v / v). 43.0 mg, yield: 67%, brown solid.mp: 130.8-131.9℃. 1 H NMR (600MHz, CDCl3) δ8.43(s,1H),8.20(d,J=8.5Hz,1H),7.83(d,J=8.2Hz,1H),7.75(d,J=7.9Hz,1H),7.5(t,J=7.0Hz,1H),7.45(t,J=7.6Hz,1H),7. 43–7.37(m,2H),7.32(d,J=8.2Hz,2H),7.07(d,J=8.2Hz,2H),3.70(d,J=1 4.3Hz,1H),3.59(d,J=14.3Hz,1H),2.50(s,1H),2.28(s,3H),1.55(s,3H). 13 C NMR (150MHz, CDCl3) δ173.5,134.9,134.1,134.1,133.3,132.2,129.5,129.2,1 28.9,128.1,126.34,150.5,124.7,120.1,77.2,41.2,26.8,21.0.HRMS(ESI)m / z Calcd for C 21 H 21 NO2[M+H] + :320.1645; Found:320.1647.

[0108] Example 24

[0109]

[0110] The reaction procedure and operation were the same as in Example 1, except that 2 g (150.5 mg, 0.5 mmol) of the substitute compound (2a) was added to the reaction system. The reaction was stopped after 48 h of irradiation with ultraviolet light (390-395 nm). Post-processing yielded the target product 3S (26.5 mg, yield 34%) as a brown solid. The parameters of the product obtained were as follows: 2-hydroxy-3-(4-iodophenyl)-2-methyl-N-(p-tolyl)acrylamide (3S): new compound. (Eluent: petroleum ether (60-90 °C) / EtOAc = 10:1, v / v). 26.5 mg, yield: 34%, yellow solid. mp: 98.3-99.5 °C. 1 H NMR (400MHz, CDCl3) δ8.38(s,1H),7.61(d,J=8.3Hz,2H),7.35(d,J=8.6Hz,2H),7.12(d,J=7.9Hz,2 H), 6.99 (d, J = 8.3Hz, 2H), 3.32 (d, J = 13.6Hz, 1H), 2.82 (d, J = 13.7Hz, 1H), 2.31 (s, 3H), 1.53 (s, 3H). 13 C NMR(150MHz, CDCl3)δ172.9,137.7,135.5,134.7,134.3,132.5,129.6,120.0,93.0,76.5,45.2,26.7,21.0.HRMS(ESI)m / zCalcd for C 17 H 18 INO2[M+Na] + :418.0280; Found:418.0284.

[0111] Example 25

[0112]

[0113] The reaction procedure and operation were the same as in Example 1, except that the starting material added to the reaction system was 2k (126.5 mg, 0.5 mmol) substituted for compound (2a). The reaction was stopped after 48 h of irradiation with ultraviolet light (390-395 nm). Post-treatment yielded a white solid, 3t (39.8 mg, yield 53%). The parameters of the product obtained were determined by nuclear magnetic resonance (NMR) and high-resolution mass spectrometry: 3-(4-bromophenyl)-2-hydroxy-2-methyl-N-(p-tolyl)propionamide (3t): new compound. (Eluent: petroleum ether (60-90 °C) / EtOAc = 10:1, v / v). 39.8 mg, yield: 53%, yellow solid. mp: 133.6-134.6 °C. 1 H NMR (400MHz, CDCl3) δ8.38(s,1H),7.41(d,J=8.4Hz,2H),7.35(d,J=8.5Hz,2H),7.12(d,J=8.4 Hz,4H),3.33(d,J=13.7Hz,1H),2.84(d,J=13.7Hz,1H),2.32(s,1H),2.31(s,3H),1.54(s,3H). 13 C NMR(100MHz, CDCl3)δ173.2,134.9,134.6,134.4,132.2,131.6,129.6,121.3,120.1,76.4,45.2,26.6,21.0.HRMS(ESI)m / z Calcdfor C 17 H 18 BrNO2[M+K] + :386.0153; Found:386.0158.

[0114] Example 26

[0115]

[0116] The reaction procedure and operation were the same as in Example 1, except that the starting material added to the reaction system was 2l (96.5 mg, 0.5 mmol) of the substitute compound (2a). The reaction was stopped after 48 h of irradiation with ultraviolet light (390-395 nm). Post-treatment yielded a white solid, 3u (27.0 mg, yield 48%). The parameters of the product obtained were determined by nuclear magnetic resonance (NMR) and high-resolution mass spectrometry: 3-(4-fluorophenyl)-2-hydroxy-2-methyl-N-(p-tolyl)propionamide (3u): new compound. (Eluent: petroleum ether (60-90 °C) / EtOAc = 10:1, v / v). 27.0 mg, yield: 48%, yellow solid. mp: 126.2-128.1 °C. 1 H NMR (400MHz, CDCl3) δ8.38(s,1H),7.35(d,J=8.5Hz,2H),7.18-7.12(m,2H),7.11(d,J=7.9Hz,2H),6.97 (t,J=8.8Hz,2H),3.36(d,J=13.8Hz,1H),2.86(d,J=13.7Hz,1H),2.33(s,1H),2.31(s,3H),1.54(s,3H). 13 C NMR(100MHz,CDCl3)δ173.3,162.2(d,J C-F =244.0Hz),134.7,134.3,131.9(d,J C-F =8.0Hz), 131.6(d,J C-F =3.0Hz),129.6,120.1,115.4(d,J C-F =21.0Hz),76.5,76.5,45.0,26.5,21.0.HRMS(ESI)m / z Calcdfor C 17 H 18 FNO2[M+H] + Found: 288.1394; Found: 288.1387.

[0117] Example 27

[0118]

[0119] The reaction procedure and operation were the same as in Example 1, except that the starting material added to the reaction system was 2m (96.5 mg, 0.5 mmol) substituted for compound (2a). The reaction was stopped after 48 h of irradiation with ultraviolet light (390-395 nm). Post-treatment yielded the target product 3v (20.0 mg, yield 35%) as a white solid. The parameters of the product obtained were as follows: 3-(3-fluorophenyl)-2-hydroxy-2-methyl-N-(p-tolyl)propionamide (3v): new compound. (Eluent: petroleum ether (60-90 °C) / EtOAc = 10:1, v / v). 20.0 mg, yield: 35%, yellow solid. mp: 118.2-119.3 °C. 1 H NMR (600MHz, CDCl3) δ8.44(s,1H),7.34(d,J=8.0Hz,2H),7.21-7.24(m,1H),7.10(d,J=8.0Hz,2H),7.02-6.97(m, 2H), 6.93 (t, J = 8.5Hz, 1H), 3.33 (d, J = 13.3Hz, 1H), 2.89 (d, J = 13.3Hz, 1H), 2.68 (s, 1H), 2.30 (s, 3H), 1.53 (s, 3H). 13 C NMR(150MHz,CDCl3)δ173.1,162.9(d,J C-F =203.8Hz), 138.6(d,J) C-F =6.3Hz),134.7,134.3,130.1(d,J C-F =7.5Hz), 129.6, 126.2 (d, J) C-F =1.3Hz), 120.1, 117.4 (d, J) C-F =17.5Hz), 114.2(d,J C-F =17.5Hz),76.5,45.5,26.6,21.0.HRMS(ESI)m / z Calcd for C 17 H 18 FNO2[M+H] + :288.1400;Found:288,1405.

[0120] Example 28

[0121]

[0122] The reaction procedure and operation were the same as in Example 1, except that the starting material added to the reaction system was 2n (104.5 mg, 0.5 mmol) substituted compound (2a), and the reaction was carried out under ultraviolet light (390-395 nm) for 48 h. The reaction was stopped, and after post-treatment, the target product 3w (21.3 mg, yield 35%) was obtained as a white solid. The parameters of the obtained product were detected by nuclear magnetic resonance and high-resolution mass spectrometry: 3-(3-chlorophenyl)-2-hydroxy-2-methyl-N-(p-tolyl)propionamide (3w): new compound. (Eluent: petroleum ether (60-90℃) / EtOAc = 10:1, v / v). 21.3 mg, yield: 35%, yellow solid. mp: 111.2-113.0℃. 1 H NMR (600MHz, CDCl3) δ8.40(s,1H),7.36(t,J=3.1Hz,1H),7.34(t,J=3.7Hz,1H),7.27(d,J=3.8Hz,1H),7.23(t,J=2. 8Hz,1H),7.15-7.08(m,4H),3.32(d,J=13.7Hz,1H),2.88(d,J=13.7Hz,1H),2.36(s,1H),2.31(s,3H),1.54(s,3H). 13 C NMR (150MHz, CDCl3) δ183.2,172.9,137.9,134.7,134.4,134.4,130.6,129.9,129.6,128.7,127.5,120.2,76.5,45.4,26.6,21.0.HRMS (ESI) m / z Calcd for C 17 H 18 ClNO2[M+H] + :304.1099; Found:304.1096.

[0123] Example 29

[0124]

[0125] In a dry, clean, transparent quartz tube, the following compounds were added sequentially: substrate (1k) (0.2 mmol, 35.0 mg), compound (2a) (0.4 mmol, 2.0 equiv., 75.6 mg), B(C6F5)3 0.02 M (final concentration in the reaction solvent, the same in the following examples), and EsionY-Na2 0.01 M (final concentration in the reaction solvent, the same in the following examples). Then, 2 mL of CH3OH solvent was added, and the reaction was carried out under blue light (460-465 nm) for 24 h. The post-treatment process was as follows: after the reaction was complete, 5 mL of water was added to the reaction system to quench the reaction, and the aqueous mixture was extracted with ethyl acetate (3 × 5 mL, 3 times, 5 mL each time). After extraction, the organic phase was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The solution was then purified by column chromatography (eluent: petroleum ether / ethyl acetate 40:1-15:1, v / v, (in this case 15:1)) to obtain a brown liquid 4a (30.1 mg, yield 58%). The product parameters were determined by nuclear magnetic resonance and high-resolution mass spectrometry: 1,3-dimethyl-3-(4-methylbenzyl)indololin-2-one (4a): known compound. (Eluent: petroleum ether (60-90℃) / EtOAc = 20:1, v / v). 30.1 mg, yield: 58%, yellow oil. 1 H NMR (400MHz, CDCl3) δ7.19(td,J=7.7,1.3Hz,1H),7.09-7.71(m,1H),7.02(t,J=7.1Hz,1H),6.86(d,J=8.1Hz,2H),6.74(d, J=8.0Hz,2H),6.64(d,J=7.4Hz,1H),3.06(d,J=13.1Hz,1H),3.01(s,3H),2.97(d,J=13.1Hz,1H),2.21(s,3H),1.45(s,3H). 13 C NMR (100MHz, CDCl3) δ180.2,143.3,136.0,133.3,133.2,129.9,128.3,127.8,123.5,122.1,107.9,50.0,44.2,26.0,22.9,21.1.

[0126] Example 30

[0127]

[0128] The reaction procedure and operation were the same as in Example 29, except that 1L (37.8 mg, 0.2 mmol) of the starting material was added to the reaction system to replace the substrate (1k), and B(C6F5)3 (0.01 M, final concentration in the reaction solvent) was added. The reaction was carried out under blue light (460-465 nm) irradiation for 24 h. The reaction was stopped, and after post-processing, the target product 4b (28.4 mg, yield 51%) was obtained as a yellow liquid. The parameters of the obtained product were determined by nuclear magnetic resonance and high-resolution mass spectrometry: 1-ethyl-3-methyl-3-(4-methylbenzyl)indoline-2-one (4b): 30.5 mg, yield: 51%, yellow liquid. 1 ¹H NMR (600MHz, CDCl₃) Novel compound. (Eluent: petroleum ether (60-90℃) / EtOAc = 20:1, v / v). 28.4 mg, yield: 51%, yellow oil. 1 H NMR (600MHz, CDCl3) δ7.18(t,J=8.4Hz,2H),7.04(t,J=7.4Hz,1H),6.84(d,J=7.7Hz,2H),6.71(d,J=7.9Hz,2H),6.64(d,J=7.6Hz,1H) ,3.68-3.74(m,1H),3.37-3.43(m,1H),3.09(d,J=13.1Hz,1H)2.98(d,J=13.1Hz,1H),2.19(s,3H),1.46(s,3H),0.89(t,J=7.2Hz,3H). 13 C NMR (150MHz, CDCl3) δ179.6,142.5,135.9,133.6,133.2,129.9,128.3,127.7 ,123.5,121.9,108.0,49.9,44.4,34.3,23.0,21.1,12.2.HRMS(ESI)m / zCalcd forC 19 H 21 NO[M+Na] + :330.1828;Found:330.1822;

[0129] Example 31

[0130]

[0131] The reaction procedure and operation were the same as in Example 29, except that the reactant added to the reaction system was 1m (43.4 mg, 0.2 mmol) instead of the substrate (1k), and B(C6F5)3 (0.01 M, final concentration in the reaction solvent) was added. The reaction was carried out under blue light (460-465 nm) irradiation for 36 h. The reaction was stopped, and after post-processing, the target product 4d (32.9 mg, yield 54%) was obtained as a yellow liquid. The parameters of the obtained product were detected by nuclear magnetic resonance and high-resolution mass spectrometry: 1-butyl-3-methyl-3-(4-methylbenzyl)indoline-2-one (4d): new compound. (Eluent: petroleum ether (60-90℃) / EtOAc=20:1, v / v). 32.9 mg, yield: 54%, yellow oil. 1 H NMR (600MHz, CDCl3) δ7.18(d,J=7.5Hz,2H),7.03(t,J=7.5Hz,1H),6.83(d,J =7.8Hz,2H),6.71(d,J=7.9Hz,2H),6.63(d,J=7.6Hz,1H),3.66-3.60(m,1H), 3.37-3.29(m,1H),3.08(d,J=13.1Hz,1H),2.99(d,J=13.1Hz,1H),2.19(s,3 H),1.45(s,3H),1.23-1.30(m,2H),1.03-1.12(m,2H),0.82(t,J=7.3Hz,3H). 13 C NMR (150MHz, CDCl3) δ179.8,143.0,136.0,133.6,133.3,129.9,128.3,127.7,12 3.5,121.9,108.2,49.9,44.2,39.6,29.5,23.4,21.1,20.2,13.9.HRMS(ESI)m / z Calcd for C 21 H 25 NO[M+H] + :280.1696; Found:280.1690.

[0132] Example 32

[0133]

[0134] The reaction procedure and operation were the same as in Example 29, except that the reactant added to the reaction system was 1n (50.2 mg, 0.2 mmol) instead of the substrate (1k), and B(C6F5)3 (0.01 M, final concentration in the reaction solvent) was added. The reaction was carried out under blue light (460-465 nm) irradiation for 36 h. The reaction was stopped, and after post-processing, the target product 4e (32.5 mg, yield 48%) was obtained as a brown liquid. The parameters of the obtained product were detected by nuclear magnetic resonance and high-resolution mass spectrometry: 1,3-dimethyl-3-(4-methylbenzyl)-5-phenylindololin-2-one (4e): new compound. (Eluent: petroleum ether (60-90℃) / EtOAc=20:1, v / v). 32.5 mg, yield: 48%, brown oil. 1 H NMR (600MHz, CDCl3) δ7.56-7.53(m,2H),7.46-7.40(m,3H),7.33(t,J=7.4Hz,1H),7.28(d,J=1.5Hz,1H),6.89(d,J=7.7Hz,2H),6. 80(d,J=7.9Hz,2H),6.71(d,J=8.0Hz,1H),3.08(d,J=13.2Hz,1H),3.05(s,3H),3.03(d,J=13.2Hz,1H),2.23(s,3H),1.49(s,3H). 13 C NMR (150MHz, CDCl3) δ180.3,142.7,141.3,136.1,135.5,133.9,133.2,130.0,128.9, 128.4,127.0,126.9,126.7,122.5,108.1,50.1,44.2,26.2,22.8,21.1.HRMS(ESI)m / z Calcd for C 24 H 23 NO[M+Na] + :364.1672; Found:364.1664.

[0135] Example 33

[0136]

[0137] The reaction procedure and operation were the same as in Example 29, except that the starting material added to the reaction system was 1o (46.2 mg, 0.2 mmol) instead of the substrate (1k), and B(C6F5)3 (0.01 M, final concentration in the reaction solvent) was added. The reaction was carried out under blue light (460-465 nm) irradiation for 36 h. The reaction was stopped, and after post-processing, the target product 4f (37.7 mg, yield 59%) was obtained as a brown liquid. The parameters of the obtained product were 5-(tert-butyl)-1,3-dimethyl-3-(4-methylbenzyl)indololin-2-one (4f): new compound. (Eluent: petroleum ether (60-90℃) / EtOAc=20:1, v / v). 37.7 mg, yield: 59%, yellow oil. 1 H NMR (600MHz, CDCl3) δ7.20(td,J=7.7,1.1Hz,1H),7.09(d,J=8.1Hz,3H),7.03(t,J=7.9Hz,1H),6.79( d,J=8.2Hz,2H),6.64(d,J=7.7Hz,1H),3.01(d,J=4.1Hz,2H),2.99(s,3H),1.45(s,3H),1.23(s,9H). 13 C NMR (150MHz, CDCl3) δ180.4,145.1,140.7,135.9,133.2,132.8,130.0,128.2 ,124.0,121.1,107.1,49.8,44.0,34.5,31.6,26.0,22.4,21.0.HRMS(ESI)m / z Calcd for C 22 H 27 NO[M+Na] + Found: 344.1985; Found: 344.1979.

[0138] Example 34

[0139]

[0140] The reaction procedure and operation were the same as in Example 29, except that 1p (50.6 mg, 0.2 mmol) was added to the reaction system to replace the substrate (1k), and B(C6F5)3 (0.01 M, final concentration in the reaction solvent) was added. The reaction was carried out under blue light (460-465 nm) irradiation for 36 h. The reaction was stopped, and after post-processing, 4 g (29.3 mg, yield 43%) of the target product, a brown liquid, was obtained. The parameters of the product, detected by nuclear magnetic resonance and high-resolution mass spectrometry, were: 5-bromo-1,3-dimethyl-3-(4-methylbenzyl)indololin-2-one (4 g): new compound. (Eluent: petroleum ether (60-90℃) / EtOAc = 20:1, v / v). 29.3 mg, yield: 43%, yellow oil. 1 H NMR (600MHz, CDCl3) δ7.30(dd,J=8.2,1.9Hz,1H),7.23(d,J=1.9Hz,1H),6.89(d,J=7.8Hz,2H),6.74(d,J=7.9Hz, 2H), 6.50 (d, J = 8.2Hz, 1H), 3.07 (d, J = 13.2Hz, 1H), 2.97 (s, 3H), 2.94 (d, J = 13.2Hz, 1H), 2.22 (s, 3H), 1.44 (s, 3H). 13 C NMR (150MHz, CDCl3) δ179.6,142.3,136.3,135.5,132.7,130.6,129.8,128.5,126.7,114.8,109.3,50.3,44.2,26.1,22.7,21.1.HRMS(ESI)m / z Calcd for C 18 H 18 BrNO[M+Na] + :366.0464; Found:366.0458.

[0141] Example 35

[0142]

[0143] The reaction procedure and operation were the same as in Example 29, except that the starting material added to the reaction system was 2b (70.0 mg, 0.4 mmol) replacing compound (2a), B(C6F5)3 (0.01 M, final concentration in the reaction solvent), and the reaction was carried out under blue light (460-465 nm) irradiation for 36 h. The reaction was stopped, and after post-treatment, the target product 4h (16.4 mg, yield 33%) was obtained. The parameters of the obtained product were detected by nuclear magnetic resonance and high-resolution mass spectrometry: 3-benzyl-1,3-dimethylindolin-2-one (4h): 16.4 mg, yield: 33%. (Eluent: petroleum ether (60-90℃) / EtOAc = 20:1, v / v). 16.3 mg, yield: 33%, yellow oil. 1 H NMR (600MHz, CDCl3) δ7.18 (td, J=7.6, 1.2Hz, 1H), 7.13 (d, J=7.3Hz, 1H), 7.02-7.04 (m, 4H), 6.85 (dd, J=7.6, 3.1Hz, 2H), 6.61 (d, J = 7.7Hz, 1H), 3.12 (d, J = 13.0Hz, 1H), 3.01 (d, J = 13.1Hz, 1H), 2.99 (s, 3H), 1.48 (s, 3H). 13 CNMR(150MHz, CDCl3)δ180.1,143.3,136.3,133.2,130.0,127.9,127.6,126.6,123.4,122.2,107.9,50.1,44.7,26.0,22.9.

[0144] Example 36

[0145]

[0146] The reaction procedure and operation were the same as in Example 29, except that the starting material added to the reaction system was 2 g (81.2 mg, 0.4 mmol) of the substitute compound (2a) and B(C6F5)3 (0.01 M, final concentration in the reaction solvent). The reaction was carried out under blue light (460-465 nm) irradiation for 36 h. The reaction was stopped, and after post-processing, the target product 4k (27.7 mg, yield 50%) was obtained as a yellow liquid. The parameters of the obtained product were detected by nuclear magnetic resonance and high-resolution mass spectrometry: 3-(4-ethylbenzyl)-1,3-dimethylindolin-2-one (4k): new compound. (Eluent: petroleum ether (60-90℃) / EtOAc=20:1, v / v). 28.1 mg, yield: 50%, yellow oil. 1H NMR (600MHz, CDCl3) δ7.19(td,J=7.7,1.1Hz,1H),7.10(d,J=7.3Hz,1H),7.03(t,J=6.8Hz,1H),6.89(d,J=7.9Hz,2H),6.77(d,J=8.0Hz ,2H),6.63(d,J=7.7Hz,1H),3.05(d,J=13.1Hz,1H),2.99(d,J=14.0Hz,4H),2.51(q,J=7.6Hz,2H),1.45(s,3H),1.13(t,J=7.6Hz,3H). 13 C NMR (150MHz, CDCl3) δ180.3,143.3,142.5,133.5,133.4,130.0,127.8,127.1,123.5,122.1,107.9,50.0,44.2,28.5,26.0,22.8,15.7.HRMS (ESI) m / z Calcd for C 19 H 21 NO[M+H] + Found: 280.16959; Found: 280.16910.

[0147] Example 37

[0148]

[0149] The reaction procedure and operation were the same as in Example 29, except that the starting material added to the reaction system was 2e (100.4 mg, 0.4 mmol) replacing compound (2a), and B(C6F5)3 (0.01 M, final concentration in the reaction solvent). The reaction was carried out under blue light (460-465 nm) irradiation for 36 h. The reaction was stopped, and after post-processing, 4l (26.5 mg, yield 41%) of the target product was obtained as a yellow liquid. The parameters of the obtained product were detected by nuclear magnetic resonance and high-resolution mass spectrometry: 3-([1,1'-biphenyl]-4-methyl)-1,3-dimethylindololin-2-one (4l): known compound. (Eluent: petroleum ether (60-90℃) / EtOAc=20:1, v / v). 32.5 mg, yield: 41%, yellow oil. 1H NMR (600MHz, CDCl3) δ7.50(d,J=7.3Hz,2H),7.39(t,J=7.7Hz,2H),7.28-7.32(m,3H),7.22-7.15(m,2H),7.05(t,J=7.4Hz, 1H), 6.92 (d, J = 8.0Hz, 2H), 6.63 (d, J = 7.7Hz, 1H), 3.15 (d, J = 13.0Hz, 1H), 3.06 (d, J = 13.0Hz, 1H), 3.01 (s, 3H), 1.50 (s, 3H). 13 CNMR (150MHz, CDCl3) δ180.1,143.3,140.9,139.2,135.5,133.2,130.4,128 .8,128.0,127.2,127.0,126.3,123.4,122.2,108.0,50.1,44.3,26.1,22.9.

[0150] Example 38

[0151]

[0152] The reaction procedure and operation were the same as in Example 29, except that the starting material added to the reaction system was 2c (92.4 mg, 0.4 mmol) replacing compound (2a), and B(C6F5)3 (0.01 M, final concentration in the reaction solvent). The reaction was carried out under blue light (460-465 nm) irradiation for 36 h. The reaction was stopped, and after post-processing, the target product 4m (26.5 mg, yield 41%) was obtained as a yellow liquid. The parameters of the obtained product, detected by nuclear magnetic resonance and high-resolution mass spectrometry, were: 3-(4-tert-butylbenzyl)-1,3-dimethylindolin-2-one (4m): known compound. (Eluent: petroleum ether (60-90℃) / EtOAc = 20:1, v / v). 26.8 mg, yield: 44%, yellow oil. 1 H NMR (600MHz, CDCl3) δ7.20(t,J=8.8Hz,1H),7.09(d,J=8.1Hz,3H),7.03(t,J=7.4Hz,1H),6.79(d, J=8.2Hz,2H),6.64(d,J=7.7Hz,1H),3.01(d,J=4.1Hz,2H),2.99(s,3H),1.45(s,3H),1.23(s,9H). 13C NMR (150MHz, CDCl3) δ180.3,149.4,143.3,133.4,133.2,129.7,127.8,124.5,123.5,122.1,107.8,49.9,44.1,34.4,31.4,26.0,22.6.

[0153] Example 39

[0154]

[0155] The reaction procedure and operation were the same as in Example 29, except that the starting material added to the reaction system was 2l (77.2 mg, 0.4 mmol) of the substitute compound (2a), and B(C6F5)3 (0.01 M, final concentration in the reaction solvent). The reaction was carried out under blue light (460-465 nm) irradiation for 36 h. The reaction was stopped, and after post-processing, the target product 4n (21.3 mg, yield 40%) was obtained as a yellow liquid. The parameters of the obtained product were 3-(4-fluorobenzyl)-1,3-dimethylindolin-2-one (4n): known compound. (Eluent: petroleum ether (60-90℃) / EtOAc=20:1, v / v). 21.4 mg, yield: 40%, yellow oil. 1 H NMR (600MHz, CDCl3) δ7.19(td,J=7.7,1.1Hz,1H),7.16(d,J=7.3Hz,1H),7.05(t,J=7.6Hz,1H),6.78(dd,J=5.8,2. 8Hz, 2H), 6.72 (t, J = 8.8Hz, 2H), 6.62 (d, J = 7.7Hz, 1H), 3.11 (d, J = 13.2Hz, 1H), 2.97 (d, J = 14.6Hz, 4H), 1.47 (s, 3H). 13 CNMR(150MHz,CDCl3)δ179.9,161.8(d,J C-F =243.0Hz),143.3,132.9,132.1(d,J C-F =4.6Hz), 131.3(d,J C-F =7.6Hz),128.0,123.2,122.3,114.5(d,J C-F =21.0Hz),108.0,50.2,43.9,26.0,22.9.

[0156] Example 40

[0157]

[0158] The reaction procedure and operation were the same as in Example 29, except that the starting material added to the reaction system was 2m (81.2 mg, 0.4 mmol) replacing compound (2a), B(C6F5)3 (0.01 M, final concentration in the reaction solvent), and the reaction was carried out under blue light (460-465 nm) irradiation for 36 h. The reaction was stopped, and after post-processing, the target product 4o (29.6 mg, yield 53%) was obtained as a yellow liquid. The parameters of the obtained product, detected by nuclear magnetic resonance and high-resolution mass spectrometry, were 3-(3,4-dimethylbenzyl)-1,3-dimethylindolin-2-one (4o): known compound. (Eluent: petroleum ether (60-90℃) / EtOAc=20:1, v / v). 29.6 mg, yield: 53%, yellow oil. 1 H NMR (600MHz, CDCl3) δ7.18(td,J=7.7,1.2Hz,1H),7.08(d,J=7.2Hz,1H),7.02(t,J= 7.8Hz,1H),6.81(d,J=7.7Hz,1H),6.65(d,J=7.9Hz,2H),6.58(d,J=7.6Hz,1H),3.01 3.02(s,3H),3.01(d,J=13.0Hz,1H),2.95(d,J=13.14Hz,1H),2.12(s,3H),2.08(s,3H),1.44(s,3H). 13 C NMR (150MHz, CDCl3) δ180.4,143.3,135.7,134.6,133.7,133.5,131.4,128 .9,127.8,127.4,123.6,122.1,107.9,49.9,44.1,26.1,22.8,19.6,19.4.

[0159] Example 41

[0160] The reaction procedure and operation were the same as in Example 29, except that water (2 mL) was used instead of CH3OH in the reaction system, along with eosin Y disodium salt (0.005 M, final concentration in the reaction solvent, the same in the following examples) and B(C6F5)3 (0.01 M, final concentration in the reaction solvent, the same in the following examples). The reaction was carried out under blue light (460-465 nm) irradiation for 24 h. The reaction was then stopped, and the target product was not obtained after post-treatment.

[0161] Example 42

[0162] The reaction procedure and operation were the same as in Example 29, except that ethanol (2 mL) was used as the solvent instead of CH3OH, and eosin Y disodium salt (0.005 M, final concentration in the reaction solvent, the same in the following examples) and B(C6F5)3 (0.01 M, final concentration in the reaction solvent, the same in the following examples) were added. The reaction was carried out under blue light (460-465 nm) irradiation for 24 h. The reaction was stopped, and the target product 4a (23.1 mg, yield 44%) was obtained after post-processing.

[0163] Example 43

[0164] The reaction procedure and operation were the same as in Example 29, except that the reaction system used methanol as the solvent (2 mL), Eosin (0.005 M, final concentration in the reaction solvent, the same in the following examples), and B(C6F5)3 (0.01 M, final concentration in the reaction solvent, the same in the following examples), and reacted under blue light (460-465 nm) irradiation for 24 h. The reaction was stopped, and after post-processing, the target product 4a (16.4 mg, yield 31%) was obtained.

[0165] Example 44

[0166] The reaction procedure and operation were the same as in Example 29, except that the reaction system used methanol as the solvent (2 mL), Eosin B (0.005 M, final concentration in the reaction solvent, the same in the following examples), and B(C6F5)3 (0.01 M, final concentration in the reaction solvent, the same in the following examples), and reacted under blue light (460-465 nm) irradiation for 24 h. The reaction was stopped, and after post-processing, the target product 4a (24.4 mg, yield 46%) was obtained.

[0167] The embodiments described above are merely preferred embodiments of the present invention and are not intended to limit the scope of the present invention. Various modifications and improvements made by those skilled in the art to the technical solutions of the present invention without departing from the spirit of the present invention should fall within the protection scope defined by the claims of the present invention.

Claims

1. A method for synthesizing α-hydroxy amide or 3,3-disubstituted oxindole, characterized in that: a double functionalization product containing an α-hydroxy amide skeleton, i.e. an α-hydroxy amide compound, is obtained by reacting an aryl triazene and an α,β-unsaturated amide as raw materials in a reaction solvent under irradiation of visible light in the presence of air and / or oxygen; or, when the H on the nitrogen of the α,β-unsaturated amide, i.e. the amide group, is replaced by a substituent, a 3,3-disubstituted oxindole compound is obtained by reacting the aryl triazene and the α,β-unsaturated amide with a protective group on the nitrogen in a reaction solvent with the addition of a photosensitizer and an additive under irradiation of visible light in the presence of air and / or oxygen; the visible light in the reaction is violet light with a wavelength of 390 nm-435 nm; the aryl triazene has the following structure: the α,β-unsaturated amide has the following structure: the α,β-unsaturated amide with a protective group on the nitrogen has the following structure: the double functionalization product containing the α-hydroxy amide skeleton has the following structure 1, and the 3,3-disubstituted oxindole compound has the following structure 2: in the structure of the above compounds, the substituent R1 is one or two or more of a phenyl group, a naphthyl group and a substituted aryl group, the substituted aryl group is a substituted phenyl group and / or a substituted naphthyl group, and the number of substituents on the substituted aryl group is 1-5; the substituents in the substituted aryl group are one or two or more of fluorine, chlorine, bromine, iodine, a phenyl group, a methoxy group, an ethoxy group, an ethyl group, a tert-butyl group, a nitro group and a 3,5-dimethyl group; the substituent R2 is one or two or more of a phenyl group, a naphthyl group and a substituted aryl group; the substituted aryl group is a substituted phenyl group and / or a substituted naphthyl group, and the number of substituents on the substituted aryl group is 1-5; the substituents in the substituted aryl group are one or two or more of fluorine, chlorine, bromine, iodine, a nitro group, a methoxy group, an ethoxy group, an ethyl group, a tert-butyl group and a 3,5-dimethyl group; the substituent R3 is one or two or more of fluorine, chlorine, bromine, iodine, a methoxy group, a nitro group and a 3,5-dimethyl group; and the number of substituents is 1-5; the substituent R4 is at least one or two or more of a methyl group, a n-butyl group, an ethyl group and a benzyl group; the reaction solvent used for synthesizing the double functionalization product containing the α-hydroxy amide skeleton is one or two or more of ethanol, acetonitrile, acetonitrile / water with a volume ratio of 3:1-1:1, dichloromethane, dichloroethane and methanol; the photosensitizer used in the reaction is any one or two or more of Acid red, Eosin Y-Na2, Eosin B and Eosin; and the additive used in the reaction is one or two or more of boron trifluoride etherate, trifluoroacetic acid and B(C6F5)3. : The synthesis conditions of the double functionalization product containing the α-hydroxy amide skeleton are as follows: the aryl triazene and the α,β-unsaturated amide are used as substrates, and the violet light induces the reaction of the aryl triazene and the α,β-unsaturated amide to synthesize the double functionalization product containing the α-hydroxy amide skeleton. ​ ​ ​ ​ ​ ​ ​ ​ ​ 2. The method of claim 1, wherein ​ The visible light in the reaction is violet light with a wavelength of 390-435 nm.

3. The synthesis method according to claim 1 or 2, wherein, The reaction solvent used in the synthesis of the bifunctional product of the α-hydroxy amide skeleton is acetonitrile / water with a volume ratio of 2:1-1:

1.

4. The method of synthesis of claim 1 or 2, wherein: The molar ratio of the α,β-unsaturated amide to aryl triazene used in the reaction is 0.2:0.1-0.

5.

5. The method of synthesis of claim 1, wherein The synthesis conditions of the 3,3-disubstituted oxindole compound are as follows: under blue light irradiation, an α,β-unsaturated amide with a protecting group on nitrogen and aryl triazene are used as substrates, the blue light induces the reaction of the α,β-unsaturated amide with a protecting group on nitrogen and triazene, and a 3,3-disubstituted oxindole compound is synthesized. The visible light in the reaction is blue light with a wavelength of 60-470 nm.

6. The synthesis method according to claim 1 or 5, wherein, The reaction solvent used in the synthesis of the 3,3-disubstituted oxindole compound is one or more of dimethyl sulfoxide, acetonitrile, dichloromethane, ethanol, and methanol.

7. The synthesis method according to claim 1 or 5, wherein, The molar ratio of the α,β-unsaturated amide with a protecting group on nitrogen to aryl triazene used in the reaction is 0.2:0.3-0.

5.

8. The synthesis method according to claim 1 or 5, wherein, The reaction is carried out in the presence of a photosensitizer, which is Eosin Y-Na2, and the concentration of the photosensitizer in the solvent is 0.005-0.02 M. The reaction is carried out in the presence of an additive, which is B(C6F5)3, and the concentration of the additive in the solvent is 0.005-0.03 M.

9. The method of synthesis of claim 1, wherein: The reaction is carried out in an atmosphere of air and / or oxygen, and the reaction time is 12-48 h.

10. The synthesis method according to claim 1, wherein, The reaction is carried out in a dry photochemical reaction vessel, the concentration of the α,β-unsaturated amide or the α,β-unsaturated amide with a protecting group on nitrogen in the reaction solvent is 0.05-0.2 M, and the concentration of the triazene in the reaction solvent is 0.1-0.5 M.

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