CN114014859A - Triazole indolol compound and synthesis method thereof - Google Patents
Triazole indolol compound and synthesis method thereof Download PDFInfo
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Abstract
The invention provides a triazole indolol compound and a synthesis method thereof, belonging to the technical field of indole multi-functionalization. The technical scheme is that indole compounds and azomethine imine are converted into isoquinoline triazole indolol and derivatives under the oxidation of acetone solution of acetone peroxide for the first time. The method synthesizes the isoquinoline triazole indolol compound by a one-pot method for the first time, and overcomes the difficulties of complicated steps, multi-step synthesis process, catalyst, high-temperature heating and the like in the synthesis method. It is suitable for use as plant protecting regulator and basic unit of main component of natural anticancer medicine.
Description
Technical Field
The application relates to an isoquinoline triazole indolol compound and a synthesis method thereof, belongs to the technical field of multifunctional synthesis of nitrogen-containing heterocyclic indole compounds from indole compounds, and particularly relates to 9-substituted-4H-indolino [1,2,4] triazolo [5,1-a ] isoquinoline-9-ol, a derivative and a synthesis method thereof.
Background
The nitrogen heterocyclic indole compound is a dominant skeleton of a plurality of active natural products and clinical drug molecules, has strong physiological and pharmacological activities of antibiosis, antiphlogosis, anticancer, antivirus and the like, plays an important role in medicine and pesticide, and is widely applied to plant protective agents and plant growth regulators of sterilization, disinsection, weeding and the like. Therefore, the method has very wide research and development prospects. At present, the common technology for synthesizing the nitrogen-containing heterocyclic indole compound utilizes the click chemical reaction of azide and alkyne, and the explosive property of the azide influences the safety of the technology. In addition, the existing technology for synthesizing the nitrogen heterocyclic ring indole compound by utilizing the multi-functionalization of indole has the problems of using a catalyst or a metal catalyst and simultaneously needing reaction conditions such as high-temperature heating and the like, and high technical cost is generated.
Disclosure of Invention
In view of the above, the present invention aims to provide a triazoloindoles compound, namely 9-substituted-4H-indolino [1,2,4] triazolo [5,1-a ] isoquinoline-9-ol and derivatives thereof, which has stable molecular structure and excellent chemical properties, is an important molecular module, and is a central skeleton containing physiologically or pharmacologically active compounds.
The invention also aims to provide a synthesis method of the triazole indole alcohol compound. The method has the advantages of scientific and reasonable process, easy operation, few reaction steps, simple required equipment, cheap and easily obtained raw materials, no need of any additional organic solvent and catalyst, no need of heating reaction, great reaction limit of atom economy, low investment and high yield, and easy industrial production and popularization.
In order to achieve the purpose, the invention adopts the following technical scheme:
a triazole indole alcohol compound has a general formula as shown in formula I:
wherein the content of the first and second substances,
R1one selected from hydrogen atom, methyl, halogen radical and methoxyl;
R2one selected from hydrogen atom, methyl, halogen group, phenyl and methoxyl;
R3selected from hydrogen atom, allyl group, propargyl group, ethylcyano group, vinyl group, substituted/unsubstituted C6-C7Aryl or substituted/unsubstituted heterocyclic radical containing nitrogen, oxygen, sulfur atoms or C1-C6Wherein the substituent of the aryl or heterocyclic group is selected from methylene or methoxy;
R4one selected from hydrogen atom, methylsulfonyl, substituted or unsubstituted phenylsulfonyl, wherein the substituent of phenylsulfonyl is selected from methyl or methoxy.
A process for synthesizing triazole indolol compounds includes such steps as mixing indole compounds with azomethine imine compounds in the presence of oxidant, reaction at low temp. by one-pot method, extracting, rotary drying to obtain coarse product, and column separation and purification.
The oxidant is acetone solution of acetone peroxide.
In the mixed reaction system, an additional organic solvent may or may not be added, and an additive may or may not be added.
The mol ratio of the indole compound to the azomethine imine compound to the oxidant is 1: 1.1-2.0: 1-5, the reaction temperature is less than or equal to 0 ℃, and the reaction time is 2-3 h.
The mol ratio of the indole compound to the azomethine imine compound to the oxidant is 1: 1.2-1.5: 2-4, the reaction temperature is-78-0 ℃, and the reaction time is 2-3 h.
The azomethine compounds are selected from C16-C24The azomethine benzene sulfonamide compound has a structural general formula as formula II:
wherein，R2One selected from hydrogen atom, methyl, halogen group, phenyl and methoxyl; r4One selected from hydrogen atom, methylsulfonyl, substituted or unsubstituted phenylsulfonyl, wherein the substituent of phenylsulfonyl is selected from methyl or methoxy.
The raw material for synthesizing azomethine imine benzene sulfonamide in the formula II is one of isochroman, 7-fluoroisochroman, 7-bromoisochroman, 7-methylisochroman, 7-bromoisochroman, benzene sulfonyl hydrazide, p-toluene sulfonyl hydrazide, 4-methoxy benzene sulfonyl hydrazide and mesitylene sulfonyl hydrazide.
The structural general formula of the indole compound is shown as formula III:
wherein R is1One selected from hydrogen atom, methyl, halogen radical and methoxyl;
R3selected from hydrogen atom, allyl group, propargyl group, ethylcyano group, vinyl group, substituted/unsubstituted C6-C7Aryl or substituted/unsubstituted heterocyclic radical containing nitrogen, oxygen, sulfur atoms or C1-C6Wherein the substituent of the aryl or heterocyclic group is selected from methylene or methoxy.
The indole compound is selected from 3-methylindole, 3-methyl-5-bromoindole, 3-methyl-6-chloroindole, 3-methyl-6-fluoroindole, 3-methyl-6-methoxyindole, 3-isopropylindole, 3-cyclohexylindole, indole-3-acetonitrile, 3-allylindole, 3-propargylindole, indole-3-ethene, 3-phenylindole, 3- (4-methoxyphenyl) indole, 3-benzylindole, 3-thienylindole, 3- (thien-2-ylmethyl) indole, 3- (furan-2-ylmethyl) indole or 3- (1-p-toluenesulfonyl-pyrrol-2-ylmethyl) indole.
The invention relates to a 9-substituted-4H-indoline [1,2,4] triazolo [5,1-a ] isoquinoline-9-ol, a derivative and a synthesis method thereof, which adopts acetone peroxide as an oxidant and an oxygen source for the first time, and adopts acetone or acetone and DMF, DCE, 1, 4-dioxane, toluene, acetonitrile and the like as mixed solvents to convert indole compounds and azomethine imine into isoquinoline triazolo-indool and the derivative. The method overcomes the defects that the triazole indole alcohol synthesis method has complex steps and can be completed by adopting a multi-step synthesis process and use a catalyst or be heated at high temperature and the like; it maintains atom economy to a great extent; the compound has stable molecular structure and excellent chemical property, and molecular blocks and compound frameworks contain rich and diverse contents of biological activity and pharmacological activity; the method also has the characteristics of mild reaction conditions, simple reaction system, simple and convenient experimental operation, less reaction equipment, wide material sources, easy expansion of application, higher product utilization value, expected market commercialization prospect and the like.
Compared with the prior art, the invention has the following beneficial effects:
(1) the invention adopts the technical scheme that indole compounds and azomethine imine are converted into isoquinoline triazole indolol and derivatives thereof under the action of acetone solution of acetone peroxide for the first time, and products with stable molecular structure and excellent chemical properties and additional products thereof are prepared;
(2) the technical scheme of converting indole compounds and azomethine into isoquinoline triazole indolol and derivatives thereof under the action of acetone solution of acetone peroxide for the first time is adopted, reaction raw materials are cheap and easy to obtain, and the reaction atom economy is high;
(3) according to the invention, the technical scheme that the indole compound and azomethine imine are converted into isoquinoline triazole indolol and the derivatives thereof under the action of acetone solution of acetone peroxide is adopted for the first time, no catalyst or additional organic solvent is needed in the reaction, raw materials are saved, and the reaction cost is reduced;
(4) the technical scheme of converting indole compounds and azomethine imine into isoquinoline triazoloindolol and derivatives thereof under the action of acetone solution of acetone peroxide for the first time is adopted, the product is directly synthesized by adopting a one-pot method, the yield is high, the dilemma of huge waste of manpower, material resources, financial resources and the like brought by the conventional multi-step synthesis method is overcome, and a large amount of development time cost and production period are saved. Meanwhile, the practical application of the product is greatly advanced, and a basic condition is created for the advanced industrial production;
(5) according to the invention, the technical scheme that the indole compound and azomethine imine are converted into isoquinoline triazole indolol and the derivatives thereof under the action of acetone solution of acetone peroxide is adopted for the first time, the temperature required by the reaction is mild, the heating reaction is not required, a large amount of energy consumption is saved, and meanwhile, the production safety is improved;
(6) the invention adopts the technical scheme that the indole compound and azomethine imine are converted into isoquinoline triazole indolol and derivatives thereof under the action of acetone solution of acetone peroxide for the first time, and the method has the advantages of scientific and reasonable process, simple and easy operation, few reaction steps and few required equipment;
(7) the invention adopts the technical scheme that indole compounds and azomethine imine are converted into isoquinoline triazole indolol and derivatives thereof under the action of acetone solution of acetone peroxide for the first time, and the preparation method has the advantages of wide raw materials and easy mass production and popularization;
(8) the technical scheme of converting indole compounds and azomethine into isoquinoline triazoloindolol and derivatives thereof under the action of acetone solution of acetone peroxide for the first time is adopted, and the method has the advantages of simple reaction system, mild reaction conditions, less reaction equipment, simple experimental operation, wide material sources, easy application expansion, high product utilization value and promising market commercialization prospect.
The invention can be widely used in the fields of medicines and pesticides such as sterilization, inflammation diminishing, cancer resistance, insect killing, weeding and the like.
Drawings
FIG. 1 is a scheme for the synthesis of compounds of the invention.
FIG. 2-1 nuclear magnetic hydrogen spectrum of the product of example 3.
FIGS. 2-2 nuclear magnetic carbon spectrum of the product of example 3.
FIG. 3-1 nuclear magnetic hydrogen spectrum of the product of example 4.
Figure 3-2 nuclear magnetic carbon spectrum of the product of example 4.
FIG. 4-1 nuclear magnetic hydrogen spectrum of the product of example 5.
Figure 4-2 nuclear magnetic carbon spectrum of the product of example 5.
FIG. 5-1 nuclear magnetic hydrogen spectrum of the product of example 6.
FIG. 5-2 nuclear magnetic carbon spectrum of the product of example 6.
FIG. 6-1 nuclear magnetic hydrogen spectrum of the product of example 8.
FIG. 6-2 nuclear magnetic carbon spectrum of the product of example 8.
Detailed Description
The present invention will be described in further detail with reference to the accompanying drawings and examples.
The general formula of the reaction system of the invention is synthesized by 9-substituted-4H-indoline [1,2,4] triazolo [5,1-a ] isoquinoline-9-ol and derivatives formed by formulas I, II and III, and is shown as follows:
wherein
R1One selected from hydrogen atom, methyl, halogen radical and methoxyl;
R2one selected from hydrogen atom, methyl, halogen group, phenyl and methoxyl;
R3selected from hydrogen atom, allyl group, propargyl group, ethylcyano group, vinyl group, substituted/unsubstituted C6-C7Aryl or substituted/unsubstituted heterocyclic radical containing nitrogen, oxygen, sulfur atoms or C1-C6Wherein the substituent of the aryl or heterocyclic group is selected from methylene or methoxy;
R4one selected from hydrogen atom, methylsulfonyl, substituted or unsubstituted phenylsulfonyl, wherein the substituent of phenylsulfonyl is selected from methyl or methoxy.
The compound synthesis comprises the following steps:
i) adding indole compounds, azomethine imine compounds and an oxidant;
ii) mixing the reactants fully, and reacting at low temperature;
iii) after the reaction is finished, purifying the obtained crude product to obtain a product;
wherein, the oxidant is preferably acetone solution of acetone peroxide, and the concentration of the acetone solution is 0.19-0.22mol/L, preferably 0.2 mol/L.
In the mixed reaction system, additional organic solvent can be added, and the organic solvent includes but is not limited to any one of DMF, DCE, 1, 4-dioxane, toluene and acetonitrile, and preferably no organic solvent is added.
In the mixed reaction system, triphenylphosphine or triphenylphosphine oxide additive, preferably triphenylphosphine, can also be added.
In order to achieve a better synthesis effect, the molar ratio of the indole compound to the azomethine imine to the acetone peroxide solution is preferably 1: 1.1-2.0: 1-5, the reaction temperature is less than or equal to 0 ℃, the reaction time is 2-3 hours, the molar ratio of the indole compound to the azomethine imine compound to the oxidant is further preferably 1: 1.2-1.5: 2-4, the reaction temperature is-78-0 ℃, and the reaction time is 2-3 hours.
The optimal scheme is that the molar ratio is 1:1.2: 3; the reaction temperature is preferably-78 ℃ to 0 ℃, and more preferably-10 ℃; the reaction time is preferably 2 h.
The raw material for synthesizing azomethine imine benzene sulfonamide is one of isochroman, 7-fluoroisochroman, 7-bromoisochroman, 7-methylisochroman, 7-bromoisochroman, benzene sulfonyl hydrazide, p-toluene sulfonyl hydrazide, 4-methoxy benzene sulfonyl hydrazide and mesitylene sulfonyl hydrazide.
The 9-substituted-4H-indoline [1,2,4] triazolo [5,1-a ] isoquinoline-9-ol and derivatives can be obtained from the process of the synthesis reaction system of the compound, and the compound is prepared by taking acetone oxide as an oxidant and an oxygen source for the first time and reacting indole compounds with azomethine imine to convert the indole compounds into isoquinoline triazoloindoles.
In conclusion, the compound has cheap reaction raw materials; the reaction does not need to use expensive catalysts and metal oxidants; the reaction is directly synthesized by a one-pot method; the method solves the problems of high cost and the like caused by the conventional multi-step synthesis method; the reaction condition is mild, no heating reaction is needed, and a series of isoquinoline triazole indolone compounds synthesized by the method have quite high potential application value.
Example 1: effect of different peroxidation Agents on the Synthesis Effect
In the preparation process, a plurality of oxidants are tried, and the best catalytic oxidation effect of the acetone peroxide is finally determined. See table 1 for details.
TABLE 1 Effect of different peroxidation Agents on Synthesis
| Serial number | Oxidizing agent | Yield (%) | Reaction state |
| 1 | H2O2 | 0 | No target product |
| 2 | m- |
0 | No target product |
| 3 | |
0 | No target product |
| 4 | TEMPO | 21 | Low synthesis speed and slow reaction |
| 5 | |
70 | The synthesis is stable, and the reaction is sufficient within 2h |
Stirring 3-methylindole (0.2mmol) and azomethine (0.22mmol) as raw materials, a hyperoxidant (2-5 times of equivalent), acetone (1mL) as a solvent at-10 ℃ for 2h, spin-drying, and performing column chromatography with petroleum ether and ethyl acetate (6: 1) to obtain a target compound white solid; wherein the hyperoxidant is shown in the following table 1: when the oxidant is 2,2,6, 6-tetramethyl piperidine oxynitride or acetone peroxide, the target product can be obtained. Wherein, the reaction effect of the acetone peroxide is best.
Example 2: influence of different reaction solvents on the Synthesis Effect
In further experiments, the same raw and auxiliary materials and reaction time are adopted, acetone solution of acetone peroxide is used as an oxidant, experiments are respectively carried out in different solvent systems, indexes such as reaction end point occurrence time, stability of a compound, purity of the compound and the like in different systems are comprehensively considered, and results show in combination with table 2 that: when the acetone solution of the acetone peroxide is adopted, no additional solvent is required to be added, and the effect is optimal.
TABLE 2 Effect of different reaction solvents on the Synthesis
| Serial number | Organic solvent | Yield (%) |
| 1 | Methylene dichloride | 73 |
| 2 | Ether (A) | 42 |
| 3 | Toluene | 55 |
| 4 | Tetrahydrofuran (THF) | 56 |
| 5 | Acetonitrile | 69 |
| 6 | Without adding any solvent | 76 |
As can be seen from table 2: no solvent is added for reaction, and the reaction effect is better.
TABLE 3 Effect of different temperatures on the Synthesis
As can be seen from table 3: due to the instability of the acetone peroxide, the reaction is more favorably carried out in a low-temperature state, and the reaction effect is the best at minus 10 ℃.
TABLE 4 influence of different proportions of the raw materials on the synthesis
As can be seen from table 4: when the molar weight of the oxidant is 2 times, the reaction is incomplete after 2 hours, and the thin-layer plate shows that the indole raw material still remains; when the molar equivalent of the oxidizing agent is 3, the reaction is complete for 2 h. Further increasing the molar amount of the oxidizing agent or azo raw material is not advantageous for increasing the yield of the reaction.
Example 3: preparation of 9-methyl-8-p-toluenesulfonyl-4H-indoline [1,2,4] triazolo [5,1-a ] isoquinoline-9-ol
A10 mL reaction tube was charged with 3-methylindole (26.2mg,0.2mmol), azomethine imine (72mg,0.24mmol), acetone peroxide solution (3mL) in acetone, followed by extraction, spin-drying, reaction with petroleum ether: ethyl acetate ═ 6:1, column chromatography and separation to obtain 66mg of the target compound as a white solid with a yield of 76%. The nuclear magnetic data and mass spectral data were as follows:
1H NMR(400MHz,CDCl3)δ7.91(d,J＝8.1Hz,2H),7.42(d,J＝7.5Hz,1H),7.39-7.27(m,5H),7.16(d,J＝7.5Hz,1H),6.83(t,J＝7.4Hz,1H),6.67(t,J＝7.7Hz,1H),5.21(d,J＝6.9Hz,1H),4.91(s,1H),4.54(s,1H),3.33(s,1H),3.12-2.96(m,1H),2.95-2.82(m,1H),2.61-2.48(m,1H),2.44(s,3H),2.43-2.31(m,1H),1.67(s,3H).13C NMR(101MHz,CDCl3)δ148.03,144.87,135.66,135.26,132.62,129.74,129.49,129.33,129.13,128.79,128.76,128.44,126.46,124.25,122.33,114.01,89.55,78.26,76.00,49.34,29.38,29.25,21.73.HRMS(ESI)calcd for C25H25N3O3Na+[M+Na]+470.1509,found 470.1512.
example 4: preparation of 11-bromo-9-methyl-8-p-toluenesulfonyl-4H-indoline [1,2,4] triazolo [5,1-a ] isoquinoline-9-ol
A10 mL reaction tube was charged with 3-methyl-5-bromoindole (42mg,0.2mmol), azomethine (72mg,0.24mmol), acetone solution of peroxyacetone (3mL) in that order, stirred at-10 ℃ for 2 hours, then spin dried, and treated with petroleum ether: ethyl acetate ═ 6: column chromatography 1 afforded 86mg of the title compound as a white solid in 82% yield. The nuclear magnetic and mass spectral data are as follows:1H NMR(400MHz,CDCl3)δ7.90(d,J＝8.0Hz,2H),7.49–7.30(m,6H),7.16(d,J＝7.5Hz,1H),6.78(d,J＝8.6Hz,1H),5.11(d,J＝8.6Hz,1H),4.91(s,1H),4.55(s,1H),3.31(s,1H),3.09–2.95(m,1H),2.91(dd,J＝10.0,5.5Hz,1H),2.57(d,J＝16.0Hz,1H),2.44(s,3H),2.43–2.32(m,1H),1.66(s,3H).13C NMR(101MHz,CDCl3)δ147.16,145.00,137.57,135.67,132.53,131.68,129.78,129.42,129.31,128.84,128.00,127.42,126.57,115.50,114.73,89.44,78.25,75.71,49.40,29.31,29.15,21.73.HRMS(ESI)calcd.for C18H16N3OBr+[M-Ts]+370.0525,found 370.0512.
example 8: preparation of 9-cyclohexyl-8-p-toluenesulfonyl-4H-indoline [1,2,4] triazolo [5,1-a ] isoquinoline-9-ol
A10 mL reaction tube was taken, and 3-cyclohexylindole (40mg,0.2mmol), azomethine (72mg,0.24mmol) and acetone solution (3mL) of acetone peroxide were added in this order, and the reaction was stirred at-10 ℃ for 2 hours, followed bySpin-drying, with petroleum ether: ethyl acetate ═ 5: column chromatography 1 afforded 85mg of the title compound as a white solid in 83% yield. The nuclear magnetic and mass spectral data are as follows:1H NMR(500MHz,CDCl3)δ7.90(d,J＝8.2Hz,2H),7.45(d,J＝7.5Hz,1H),7.38–7.31(m,3H),7.30(t,J＝7.3Hz,1H),7.23(d,J＝7.4Hz,1H),7.15(d,J＝7.6Hz,1H),6.81(t,J＝7.4Hz,1H),6.69–6.64(m,1H),5.24(d,J＝8.2Hz,1H),5.03(s,1H),4.63(s,1H),3.37(s,1H),3.05–2.93(m,1H),2.85–2.77(m,1H),2.52(d,J＝15.7Hz,1H),2.45(s,3H),2.35–2.27(m,1H),2.12–2.03(m,1H),1.90–1.63(m,4H),1.32–1.24(m,3H),1.23–1.16(m,2H),1.09–0.98(m,1H).13C NMR(126MHz,CDCl3)δ149.30,144.77,135.61,133.34,132.86,129.73,129.58,129.28,129.04,128.71,128.65,128.63,126.40,125.40,121.81,113.72,86.59,80.74,78.35,49.07,47.98,29.38,26.59,26.54,26.39,26.36,26.33,21.74.HRMS(ESI)calcd.for C23H25N3O+[M-Ts]+360.2070,found 360.2047.
example 13: preparation of 9-phenyl-8-p-toluenesulfonyl-4H-indoline [1,2,4] triazolo [5,1-a ] isoquinoline-9-ol
A10 mL reaction tube was charged with 3-phenylindole (38.6mg,0.2mmol), azomethine (72mg,0.24mmol), acetone solution (3mL) of acetone peroxide, followed by stirring at-10 ℃ for 2 hours, followed by spin-drying, and reaction with petroleum ether: ethyl acetate ═ 5: column chromatography 1 afforded 66mg of the title compound as a white solid in 62% yield. The nuclear magnetic and mass spectral data are as follows:1H NMR(400MHz,CDCl3)δ7.86(d,J＝8.2Hz,2H),7.48–7.43(m,2H),7.41(d,J＝6.4Hz,2H),7.38(d,J＝6.8Hz,2H),7.35(s,1H),7.34–7.29(m,4H),7.22(t,J＝7.7Hz,1H),6.88(t,J＝7.3Hz,1H),6.76(t,J＝7.7Hz,1H),5.36(d,J＝8.2Hz,1H),5.11(s,1H),4.52(s,1H),4.09(s,1H),3.14–3.03(m,1H),2.69–2.59(m,1H),2.59–2.53(m,1H),2.43(s,1H).13C NMR(101MHz,CDCl3)δ149.50,145.35,144.90,135.63,134.43,132.33,129.73,129.53,129.34,129.16,129.11,128.77,128.55,128.44,127.75,126.47,126.04,125.69,122.65,114.11,91.04,80.38,78.31,49.42,29.41,21.68.HRMS(ESI)calcd.for C23H20N3O+[M-Ts]+354.1656,found 354.1648.
example 15: preparation of 9-benzyl-8-p-toluenesulfonyl-4H-indoline [1,2,4] triazolo [5,1-a ] isoquinoline-9-ol
A10 mL reaction tube was charged with 3-benzylindole (41mg,0.2mmol), azomethine imine (72mg,0.24mmol), acetone solution (3mL) of acetone peroxide, followed by stirring at-10 ℃ for 2 hours, followed by spin-drying, petroleum ether: ethyl acetate ═ 6: column chromatography 1 afforded the title compound 90mg as a white solid in 86% yield. The nuclear magnetic and mass spectral data are as follows:1H NMR(400MHz,CDCl3)δ7.55(d,J＝8.2Hz,2H),7.45(d,J＝7.1Hz,1H),7.40(t,J＝7.6Hz,3H),7.37–7.31(m,3H),7.32–7.25(m,3H),7.19(d,J＝7.6Hz,1H),7.09(dd,J＝7.5,0.9Hz,1H),6.85–6.78(m,1H),6.74–6.68(m,1H),5.28(d,J＝8.1Hz,1H),4.84(s,1H),4.43(s,1H),3.82(s,1H),3.24(d,J＝13.7Hz,1H),3.13–3.00(m,2H),2.96(d,J＝13.7Hz,1H),2.64–2.53(m,1H),2.45(s,3H),2.43–2.37(m,1H).13C NMR(126MHz,CDCl3)δ148.12,144.67,135.93,135.76,134.36,131.83,131.13,129.62,129.44,129.24,129.05,128.77,128.76,128.61,128.13,126.95,126.41,124.87,122.03,114.03,86.96,78.28,78.02,49.59,47.70,29.38,21.73.HRMS(ESI)calcd.for C24H22N3O+[M-Ts]+368.1757,found 368.1715.
example 16: preparation of 9- (furan-2-ylmethyl) -8-p-toluenesulfonyl-4H-indoline [1,2,4] triazolo [5,1-a ] isoquinoline-9-ol
3- (furan-2-ylmethyl) indole (39.4mg,0.2mmol), azomethine (72mg,0.24mmol), acetone solution (3mL) of peroxyacetone were added sequentially to a 10mL reaction tube, stirred at-10 ℃ for 2 hours, then spun dry, with petroleum ether: ethyl acetate ═ 5: column chromatography 1 afforded 86mg of the title compound as a white solid in 84% yield. The nuclear magnetic and mass spectral data are as follows:
1H NMR(400MHz,CDCl3)δ7.72(d,J＝8.2Hz,2H),7.52(d,J＝1.1Hz,1H),7.47–7.40(m,1H),7.36(t,J＝6.8Hz,1H),7.31(d,J＝7.9Hz,3H),7.25(d,J＝9.4Hz,1H),7.18(d,J＝7.4Hz,1H),6.84(t,J＝7.2Hz,1H),6.73–6.68(m,1H),6.48(dd,J＝3.0,1.9Hz,1H),6.32(d,J＝3.0Hz,1H),5.27(d,J＝8.1Hz,1H),4.98(s,1H),4.45(s,1H),3.87(s,1H),3.28(d,J＝15.0Hz,1H),3.11–3.00(m,2H),2.97(d,J＝15.0Hz,1H),2.62–2.52(m,1H),2.44(s,3H),2.43–2.37(m,1H).13C NMR(101MHz,DMSO)δ150.95,148.85,144.92,142.34,135.77,134.22,133.14,130.16,129.81,129.63,129.26,129.09,128.95,128.34,126.91,125.27,121.73,113.46,111.06,109.15,87.03,78.02,77.59,49.23,29.07,21.58.HRMS(ESI)calcd.for C22H20N3O2 +[M-Ts]+358.1550,found 358.1514.
example 20: preparation of 9-allyl-8-p-toluenesulfonyl-4H-indoline [1,2,4] triazolo [5,1-a ] isoquinoline-9-ol
A10 mL reaction tube was charged with 3-allylindole (31.4mg,0.2mmol), azomethine (72mg,0.24mmol), acetone solution (3mL) of acetone peroxide, followed by stirring at-10 ℃ for 2 hours, followed by spin-drying, and reaction with petroleum ether: ethyl acetate ═ 8: column chromatography 1 afforded 67mg of the title compound as a white solid in 71% yield. The nuclear magnetic and mass spectral data are as follows:1H NMR(400MHz,CDCl3)δ7.92(d,J＝8.3Hz,1H),7.46(d,J＝7.7Hz,1H),7.40(dd,J＝7.4,1.3Hz,1H),7.38–7.34(m,1H),7.31(dd,J＝7.7,1.2Hz,1H),7.20(d,J＝7.5Hz,1H),6.86(td,J＝7.4,0.7Hz,1H),6.71(td,J＝7.9,1.4Hz,1H),6.05(ddt,J＝17.1,10.2,7.2Hz,1H),5.33–5.28(m,1H),5.24(dd,J＝17.1,1.9Hz,1H),5.00(s,1H),4.54(s,1H),3.55(s,1H),3.13–2.94(m,1H),2.77(dd,J＝14.1,6.8Hz,1H),2.64–2.53(m,1H),2.47–2.39(m,1H).13C NMR(101MHz,CDCl3)δ148.44,144.81,135.68,134.06,132.72,132.41,129.74,129.51,129.30,129.08,128.88,128.74,128.48,126.40,124.73,122.09,119.29,113.92,87.13,78.16,77.72,49.38,46.21,29.37,21.71.HRMS(ESI)calcd.for C20H20N3O+[M-Ts]+318.1601,found 318.1550.
example 21: preparation of 8-p-toluenesulfonyl-9-vinyl-4H-indoline [1,2,4] triazolo [5,1-a ] isoquinoline-9-ol
Indole-3-ethene (28.6mg,0.2mmol), azomethine (72mg,0.24mmol), acetone solution (3mL) of peroxyacetone were added to a 10mL reaction tube in this order, stirred at-10 ℃ for 2 hours, then spin dried, and treated with petroleum ether: ethyl acetate 10: column chromatography 1 afforded 62mg of the title compound as a white solid in 68% yield. The nuclear magnetic and mass spectral data are as follows:1H NMR(400MHz,DMSO)δ7.91(d,J＝8.1Hz,2H),7.52–7.46(m,3H),7.44(d,J＝7.5Hz,1H),7.37(t,J＝7.2Hz,1H),7.27(d,J＝7.7Hz,1H),7.16(d,J＝7.1Hz,1H),6.84(t,J＝7.3Hz,1H),6.73(t,J＝7.6Hz,1H),6.14(dd,J＝17.1,10.5Hz,1H),5.68(s,1H),5.22(d,J＝8.1Hz,1H),5.17(d,J＝10.6Hz,1H),5.13(d,J＝17.1Hz,1H),5.01(s,1H),4.32(s,1H),2.99–2.83(m,2H),2.63(d,J＝16.6Hz,1H),2.46(s,3H),2.43–2.30(m,1H).13C NMR(101MHz,DMSO)δ149.20,144.84,143.02,135.81,133.73,133.57,130.11,129.86,129.68,129.36,129.12,128.96,128.34,126.93,125.92,122.04,113.76,113.67,87.88,79.18,77.70,49.00,29.07,21.57.HRMS(ESI)calcd.for C26H25N3O3S+[M]+459.1509,found 459.1508.
example 22: preparation of 2, 9-dimethyl-8-p-toluenesulfonyl-4H-indoline [1,2,4] triazolo [5,1-a ] isoquinoline-9-ol
A10 mL reaction tube was charged with 3-methylindole (26.2mg,0.2mmol), 7-methylazomethine imine (75mg,0.24mmol), acetone peroxide solution (3mL) in succession, stirred at-10 ℃ for 2 hours, then spin-dried, and treated with petroleum ether: ethyl acetate 10: column chromatography 1 afforded 74mg of the title compound as a white solid in 80% yield. The nuclear magnetic data are as follows:1H NMR(400MHz,DMSO)δ7.84(d,J＝8.2Hz,2H),7.47(d,J＝8.0Hz,2H),7.29–7.17(m,3H),7.10(d,J＝7.8Hz,1H),6.76(dt,J＝7.4,3.7Hz,1H),6.72–6.66(m,1H),5.71(s,1H),5.19(d,J＝7.9Hz,1H),4.97(s,1H),4.19(s,1H),2.89–2.70(m,2H),2.49(d,J＝1.3Hz,1H),2.41(s,3H),2.31(s,3H),2.17(dd,J＝16.1,7.0Hz,1H),1.77(s,3H).13C NMR(101MHz,DMSO)δ150.16,145.03,136.14,135.83,133.16,132.54,130.45,130.25,129.87,129.29,129.13,128.96,128.27,124.48,121.75,113.43,92.06,78.24,76.73,49.23,28.67,24.48,21.60,20.94.
following the procedure described in example 3, the present invention synthesizes the following compounds:
nuclear magnetic and mass spectral data for some of the example compounds of the invention are given below:
example 5: synthesis of 12-fluoro-9-methyl-8-p-toluenesulfonyl-4H-indoline [1,2,4] triazolo [5,1-a ] isoquinoline-9-ol
1H NMR(500MHz,CDCl3)δ7.90(d,J＝8.2Hz,2H),7.38(t,J＝7.2Hz,2H),7.36–7.28(m,3H),7.25–7.15(m,2H),6.51(td,J＝8.6,2.2Hz,1H),4.92–4.86(m,2H),4.54(s,1H),3.27(s,1H),3.10–2.99(m,1H),2.95(dd,J＝9.9,5.0Hz,1H),2.60(d,J＝16.2Hz,1H),2.45(s,3H),2.44–2.38(m,1H),1.66(s,3H).19F NMR(471MHz,CDCl3)δ-112.12.13C NMR(101MHz,CDCl3)δ163.14(JC-F＝242.0Hz),149.43(JC-F＝11.8Hz),144.97,135.65,132.57,130.96(JC-F＝2.1Hz),129.78,129.45,129.30,129.26,128.93,127.82,126.64,125.08,124.98,109.12(JC-F＝23.0Hz),101.79(JC-F＝28.0Hz),89.73,78.17,75.42,49.40,29.33,21.72.HRMS(ESI)calcd.for C18H16N3OF+[M-Ts]+310.1350,found 310.1327.
Example 6: synthesis of 12-chloro-9-methyl-8-p-toluenesulfonyl-4H-indoline [1,2,4] triazolo [5,1-a ] isoquinoline-9-ol
1H NMR(500MHz,CDCl3)δ7.88(dd,J＝22.9,8.1Hz,2H),7.42–7.36(m,2H),7.36–7.29(m,3H),7.20(d,J＝7.9Hz,2H),6.83–6.77(m,1H),5.16(d,J＝1.6Hz,1H),4.91(s,1H),4.54(d,J＝10.6Hz,1H),3.29(s,1H),3.09–2.84(m,1H),2.61(d,J＝16.1Hz,1H),2.45(s,3H),2.43–2.34(m,1H),1.65(s,3H).13C NMR(101MHz,CDCl3)δ149.15,144.99,135.63,134.27,133.86,132.51,129.78,129.45,129.29,128.83,127.77,126.65,125.01,122.39,114.45,89.49,78.20,75.54,49.44,29.30,29.19,21.73.HRMS(ESI)calcd.for C18H16N3OCl+[M-Ts]+326.1031,found 326.1006.
Example 9: synthesis of 9-isopropyl-8-p-toluenesulfonyl-4H-indoline [1,2,4] triazolo [5,1-a ] isoquinoline-9-ol
1H NMR(400MHz,CDCl3)δ7.93(d,J＝8.3Hz,2H),7.48(d,J＝7.6Hz,1H),7.48(d,J＝7.6Hz,3H),7.42–7.35(m,1H),7.33(t,J＝7.2Hz,1H),7.27(dd,J＝7.5,1.0Hz,1H),7.18(d,J＝7.5Hz,1H),6.84(td,J＝7.4,0.7Hz,1H),6.76–6.63(m,1H),5.28(d,J＝8.1Hz,1H),5.00(s,1H),4.64(s,1H),3.43(s,1H),3.11–2.96(m,1H),2.89(ddd,J＝10.3,5.5,1.4Hz,1H),2.56(d,J＝16.6Hz,1H),2.48(s,3H),2.43–2.30(m,1H),2.22(hept,J＝6.8Hz,1H),1.08(d,J＝6.8Hz,3H),0.99(d,J＝6.9Hz,3H).13C NMR(101MHz,CDCl3)δ149.23,144.79,135.60,133.06,132.74,129.75,129.58,129.25,129.05,128.71,128.69,128.60,126.39,125.36,121.77,113.74,86.49,81.04,78.30,49.15,37.77,29.38,21.74,16.67,16.56.HRMS(ESI)calcd.for C20H22N3O+[M]+320.1757,found 320.1704.
Example 10: synthesis of 9-acetonitrile-8-p-toluenesulfonyl-4H-indoline [1,2,4] triazolo [5,1-a ] isoquinoline-9-ol
1H NMR(400MHz,DMSO)δ7.90(d,J＝8.1Hz,1H),7.46(d,J＝8.0Hz,1H),7.43–7.34(m,2H),7.23(d,J＝7.5Hz,1H),6.85(t,J＝7.4Hz,1H),6.75(t,J＝7.7Hz,1H),6.26(s,1H),5.18(d,J＝8.1Hz,1H),4.92(s,1H),4.23(s,1H),3.11(d,J＝16.7Hz,1H),2.92(d,J＝16.7Hz,1H),2.86(d,J＝9.4Hz,1H),2.59(d,J＝16.4Hz,1H),2.41(s,2H),2.26(dd,J＝18.5,9.0Hz,1H).13C NMR(101MHz,DMSO)δ148.86,145.01,135.83,133.26,132.35,130.14,129.85,129.79,129.75,129.48,129.20,128.09,127.03,125.49,122.07,117.92,113.77,87.24,77.68,76.20,49.17,30.98,29.03,21.58.HRMS(ESI)calcd.for C19H17N4O+[M]+317.1397,found 317.1353.
Example 11: synthesis of 9- (2- (tert-butyldimethylsilyl) oxy) ethyl) -8-p-toluenesulfonyl-4H-indolino [1,2,4] triazolo [5,1-a ] isoquinolin-9-ol
1H NMR(500MHz,CDCl3)δ7.84(dd,J＝8.2,2.0Hz,2H),7.34(d,J＝7.5Hz,1H),7.30–7.21(m,4H),7.21–7.14(m,2H),7.08(d,J＝7.4Hz,1H),6.78–6.71(m,1H),6.60(t,J＝7.1Hz,1H),5.19(d,J＝8.1Hz,1H),5.15(s,1H),4.49(s,1H),3.88(s,1H),3.86–3.80(m,1H),3.79–3.71(m,1H),2.98–2.87(m,1H),2.86–2.80(m,1H),2.46(d,J＝16.6Hz,1H),2.36(s,3H),2.33–2.29(m,1H),2.26–2.20(m,1H),2.01–1.94(m,1H),0.83(s,9H),-0.00(s,3H),-0.03(s,3H).13C NMR(126MHz,CDCl3)δ148.78,144.56,135.72,134.02,133.06,129.64,129.49,129.31,129.03,128.81,128.73,128.59,126.36,124.77,121.99,113.96,87.47,78.27,78.19,59.30,49.09,43.65,29.38,25.96,21.70,18.27,-5.42,-5.46.HRMS(ESI)calcd.for C25H35N3O2Si+[M-Ts]+437.2499,found 437.2500.
Example 12: synthesis of 1- (2- (9-hydroxy-8-p-toluenesulfonyl-4H-indoline [1,2,4] triazolo [5,1-a ] isoquinolin-9-yl) ethyl) pyrrolidine-2, 5-dione
1H NMR(500MHz,CDCl3)δ7.99(d,J＝8.2Hz,2H),7.43–7.36(m,3H),7.35–7.28(m,2H),7.16(d,J＝7.6Hz,1H),6.82(t,J＝7.4Hz,1H),6.70–6.62(m,1H),5.23(d,J＝8.2Hz,1H),5.20(s,1H),4.39(s,1H),3.92(ddd,J＝15.3,10.8,4.7Hz,1H),3.84(ddd,J＝13.8,10.4,5.9Hz,1H),3.40(s,1H),3.14–2.98(m,2H),2.69(m,4H),2.61–2.55(m,1H),2.45(s,3H),2.41–2.27(m,2H),1.99–1.90(m,1H).13C NMR(101MHz,DMSO)δ178.22,148.64,144.99,135.83,134.81,133.32,130.13,129.85,129.67,129.47,129.13,129.04,128.35,126.94,125.20,122.02,113.61,86.87,77.58,77.42,49.20,39.50,33.59,29.13,28.60,21.57.HRMS(ESI)calcd.for C23H24N4O3 +[M-Ts]+404.1848,found 404.1850.
Example 14: synthesis of 9- (thiophene-2-yl) -8-p-toluenesulfonyl-4H-indoline [1,2,4] triazolo [5,1-a ] isoquinoline-9-ol
1H NMR(400MHz,DMSO)δ7.78(dd,J＝39.7,8.3Hz,2H),7.52–7.47(m,1H),7.46–7.41(m,3H),7.40(d,J＝7.5Hz,1H),7.33(t,J＝7.1Hz,1H),7.25(t,J＝7.3Hz,2H),6.94(dd,J＝5.0,3.6Hz,1H),6.83(t,J＝7.4Hz,1H),6.77–6.69(m,1H),6.66(dd,J＝3.5,1.2Hz,1H),6.34(s,1H),5.21(d,J＝8.1Hz,1H),5.17(s,1H),4.32(s,1H),2.98–2.79(m,2H),2.63–2.56(m,1H),2.39(s,3H),2.33(d,J＝12.1Hz,1H).13C NMR(101MHz,DMSO)δ151.75,149.21,144.91,135.81,134.82,133.53,130.14,129.88,129.72,129.41,129.32,129.12,128.33,127.12,126.97,126.00,124.11,122.26,113.92,90.36,78.84,77.79,49.11,29.10,21.56.HRMS(ESI)calcd.for C21H18N3OS+[M-Ts]+360.1165,found 360.1124.
Example 25: synthesis of 2-bromo-9-methyl-8-p-toluenesulfonyl-4H-indoline [1,2,4] triazolo [5,1-a ] isoquinoline-9-ol
1H NMR(400MHz,CDCl3)δ7.89(d,J＝8.2Hz,2H),7.58(s,1H),7.48(dd,J＝8.2,1.7Hz,1H),7.36–7.30(m,3H),7.05(d,J＝8.2Hz,1H),6.86(t,J＝7.4Hz,1H),6.74(t,J＝7.7Hz,1H),5.35(d,J＝8.1Hz,1H),4.88(s,1H),4.46(s,1H),3.28(s,1H),2.96–2.90(m,2H),2.56–2.50(m,1H),2.46(s,3H),2.37(dd,J＝17.9,8.9Hz,1H),1.66(s,3H).13C NMR(101MHz,CDCl3)δ147.66,145.00,135.32,134.66,132.24,132.11,130.68,130.43,129.78,129.75,129.27,128.89,124.39,122.59,120.00,113.93,89.58,77.55,75.98,49.03,29.26,28.95,21.75,21.71.
Example 26: synthesis of 9-methyl-8-p-toluenesulfonyl-4H-benzo [ f ] indole [1,2,4] triazolo [5,1-a ] isoquinoline-9-ol
1H NMR(500MHz,CDCl3)δ7.91(dd,J＝12.4,5.7Hz,4H),7.82(d,J＝8.5Hz,1H),7.66–7.56(m,2H),7.49(d,J＝8.5Hz,1H),7.32(dd,J＝7.6,3.7Hz,3H),6.80(t,J＝7.4Hz,1H),6.64–6.54(m,1H),5.44(d,J＝8.2Hz,1H),4.98(s,1H),4.63(s,1H),3.35(s,1H),3.25–3.05(m,3H),2.53(td,J＝10.6,3.9Hz,1H),2.43(s,3H),1.70(s,3H).13C NMR(126MHz,CDCl3)δ148.01,144.88,135.12,133.30,132.60,132.26,131.36,129.73,129.37,128.86,128.72,127.25,126.92,126.81,126.38,125.51,124.26,123.64,122.27,114.09,89.74,78.73,76.05,49.05,29.28,26.15,21.72.HRMS(ESI)calcd.for C22H21N3O+[M-Ts]+343.1685,found 343.1690.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.
Claims (10)
1. A triazole indole alcohol compound is characterized in that: it has the general formula I:
wherein
R1One selected from hydrogen atom, methyl, halogen radical and methoxyl;
R2one selected from hydrogen atom, methyl, halogen group, phenyl and methoxyl;
R3selected from hydrogen atom, allyl group, propargyl group, ethylcyano group, vinyl group, substituted/unsubstituted C6-C7Aryl or substituted/unsubstituted heterocyclic radical containing nitrogen, oxygen, sulfur atoms or C1-C6Wherein the substituent of the aryl or heterocyclic group is selected from methylene or methoxy;
R4one selected from hydrogen atom, methylsulfonyl, substituted or unsubstituted phenylsulfonyl, wherein the substituent of phenylsulfonyl is selected from methyl or methoxy.
2. A synthetic method of the triazole indole alcohol compound according to claim 1, which is characterized in that: in the presence of an oxidant, mixing indole compounds and azomethine imine compounds, reacting at low temperature by a one-pot method, extracting, spin-drying to obtain a crude product, and separating and purifying by a column to obtain a product.
3. The method for synthesizing triazole indolol compounds according to claim 2, wherein the method comprises the following steps: the oxidant is acetone solution of acetone peroxide.
4. The method for synthesizing triazole indolol compounds according to claim 2, wherein the method comprises the following steps: in the mixed reaction system, an additional organic solvent may or may not be added, and an additive may or may not be added.
5. The method for synthesizing triazole indolol compounds according to claim 2, wherein the method comprises the following steps: the mol ratio of the indole compound to the azomethine imine compound to the oxidant is 1: 1.1-2.0: 1-5, the reaction temperature is less than or equal to 0 ℃, and the reaction time is 2-3 h.
6. The method for synthesizing triazole indolol compounds according to claim 2, wherein the method comprises the following steps: the mol ratio of the indole compound to the azomethine imine compound to the oxidant is 1: 1.2-1.5: 2-4, the reaction temperature is-78-0 ℃, and the reaction time is 2-3 h.
7. The method for synthesizing triazole indolol compounds according to claim 2, wherein the method comprises the following steps: the azomethine compounds are selected from C16-C24The azomethine benzene sulfonamide compound has a structural general formula as formula II:
wherein
R2One selected from hydrogen atom, methyl, halogen group, phenyl and methoxyl;
R4one selected from hydrogen atom, methylsulfonyl, substituted or unsubstituted phenylsulfonyl, wherein the substituent of phenylsulfonyl is selected from methyl or methoxy.
8. The method for synthesizing triazole indole alcohol compounds according to claim 7, wherein the method comprises the following steps: the raw material for synthesizing azomethine imine benzene sulfonamide in the formula II is one of isochroman, 7-fluoroisochroman, 7-bromoisochroman, 7-methylisochroman, 7-bromoisochroman, benzene sulfonyl hydrazide, p-toluene sulfonyl hydrazide, 4-methoxy benzene sulfonyl hydrazide and mesitylene sulfonyl hydrazide.
9. The method for synthesizing triazole indolol compounds according to claim 2, wherein the method comprises the following steps: the structural general formula of the indole compound is shown as formula III:
wherein
R1One selected from hydrogen atom, methyl, halogen radical and methoxyl;
R3selected from hydrogen atom, allyl group, propargyl group, ethylcyano group, vinyl group, substituted/unsubstituted C6-C7Aryl or substituted/unsubstituted heterocyclic radical containing nitrogen, oxygen, sulfur atoms or C1-C6Wherein the substituent of the aryl or heterocyclic group is selected from methylene or methoxy.
10. The method for synthesizing triazole indolol compounds according to claim 9, wherein the method comprises the following steps: the indole compound is selected from 3-methylindole, 3-methyl-5-bromoindole, 3-methyl-6-chloroindole, 3-methyl-6-fluoroindole, 3-methyl-6-methoxyindole, 3-isopropylindole, 3-cyclohexylindole, indole-3-acetonitrile, 3-allylindole, 3-propargylindole, indole-3-ethene, 3-phenylindole, 3- (4-methoxyphenyl) indole, 3-benzylindole, 3-thienylindole, 3- (thien-2-ylmethyl) indole, 3- (furan-2-ylmethyl) indole or 3- (1-p-toluenesulfonyl-pyrrol-2-ylmethyl) indole.
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| CN105198888A (en) * | 2015-10-01 | 2015-12-30 | 湘潭大学 | 2,3a-disubstituted-3H-pyrazole[1,5-a]indole-4(3aH)-ketone, derivative and synthetic method of 2,3a-disubstituted-3H-pyrazole[1,5-a]indole-4(3aH)-ketone and derivative |
| CN107417690A (en) * | 2017-09-07 | 2017-12-01 | 南方科技大学 | Method for efficiently and asymmetrically catalyzing and synthesizing pyrrolindoline |
| CN107501160A (en) * | 2017-09-07 | 2017-12-22 | 南方科技大学 | Method for synthesizing axial chiral aryl indole through organic catalysis |
| CN107501163A (en) * | 2017-09-07 | 2017-12-22 | 南方科技大学 | Method for synthesizing axial chiral aniline indole under catalysis of chiral phosphoric acid |
| CN113105460A (en) * | 2021-04-27 | 2021-07-13 | 扬州大学 | Synthesis method of 6-hydroisoindolo [2, 1-alpha ] indole compound |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105198888A (en) * | 2015-10-01 | 2015-12-30 | 湘潭大学 | 2,3a-disubstituted-3H-pyrazole[1,5-a]indole-4(3aH)-ketone, derivative and synthetic method of 2,3a-disubstituted-3H-pyrazole[1,5-a]indole-4(3aH)-ketone and derivative |
| CN107417690A (en) * | 2017-09-07 | 2017-12-01 | 南方科技大学 | Method for efficiently and asymmetrically catalyzing and synthesizing pyrrolindoline |
| CN107501160A (en) * | 2017-09-07 | 2017-12-22 | 南方科技大学 | Method for synthesizing axial chiral aryl indole through organic catalysis |
| CN107501163A (en) * | 2017-09-07 | 2017-12-22 | 南方科技大学 | Method for synthesizing axial chiral aniline indole under catalysis of chiral phosphoric acid |
| CN113105460A (en) * | 2021-04-27 | 2021-07-13 | 扬州大学 | Synthesis method of 6-hydroisoindolo [2, 1-alpha ] indole compound |
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