CN104262213A - Method for synthesizing alpha-aryl-beta-sulfonyl amide - Google Patents
Method for synthesizing alpha-aryl-beta-sulfonyl amide Download PDFInfo
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- CN104262213A CN104262213A CN201410439158.9A CN201410439158A CN104262213A CN 104262213 A CN104262213 A CN 104262213A CN 201410439158 A CN201410439158 A CN 201410439158A CN 104262213 A CN104262213 A CN 104262213A
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Abstract
The invention discloses a method for synthesizing alpha-aryl-beta-sulfonyl amide. The method comprises the following steps: mixing N-phenyl N-sulfonyl acrylamide compounds with p-methyl benzenesulfonyl hydrazide to obtain a mixture; then, adding a catalyst into the mixture, adding an oxidant into the mixture after dissolving the catalyst with a solvent, and reacting for 1-10 hours at 0-150 DEG C; and after the reaction is completed, separating and purifying the mixture to obtain alpha-aryl-beta-sulfonyl amide, wherein a structural formula of the N-phenyl N-sulfonyl acrylamide compounds is as shown in formula (I) described in the specification, a structural formula of the alkyl sulfonyl hydrazine is as shown in formula (II) described in the specification and a structural formula of the alpha-aryl-beta-sulfonyl amide compound is as shown in formula (III) described in the specification, wherein Ar1, Ar2 and Ar3 are independently selected from alkyl or substituted alkyl; a substituent group on substituted alkyl is alkyl with a carbon number of 5-6, alkoxy with a carbon number of 3-6 or halogen.
Description
Technical field
The present invention relates to organic synthesis field, be specifically related to a kind of method of synthesizing alpha-aromatic-'Beta '-sulfonyl acid amides.
Background technology
Make a general survey of antimicrobial drug for over ten years should be used for see, sulfamide compound due to advantages such as distinctive antibacterial general wide, stable in properties, easy to use, low prices, by extensively in clinical drug research.At present, along with the research of scientists is goed deep into, find that sulfamide compound has had biological activity more widely, as antitumor, diuresis, antithyroid, hypoglycemia, treatment cataract etc.Although its application is comparatively wide, in concrete building-up process, complex manufacturing, reactions steps is many, makes the cost of reaction large.
Summary of the invention
The invention provides a kind of method of synthesizing alpha-aromatic-'Beta '-sulfonyl acid amides, utilize catalytic oxidation, method is simple, easy handling, and aftertreatment is simple, meets industrialized production.
Synthesize a method for alpha-aromatic-'Beta '-sulfonyl acid amides, synthesis step is:
By N-aryl N-alkylsulfonyl acrylamides, arylsulfonyl hydrazine, catalyzer and oxygenant and solvent, at 0 ~ 150 DEG C, react 1 ~ 10h, after having reacted, obtain described alpha-aromatic-'Beta '-sulfonyl acid amides through separation and purification;
Step is more specifically: mixed with arylsulfonyl hydrazine by N-aryl N-alkylsulfonyl acrylamides, then add catalyzer, add oxygenant with after dissolution with solvents, then obtains described alpha-aromatic-'Beta '-sulfonyl acid amides through reaction and aftertreatment.
The structural formula of described N-aryl N-alkylsulfonyl acrylamides as shown in formula I,
The structural formula of described arylsulfonyl hydrazine is as shown in formula II;
The structural formula of described alpha-aromatic-'Beta '-sulfonyl amide compound is as shown in formula III;
In formula, Ar
1, Ar
2and Ar
3independently selected from aryl or substituted aryl, the substituting group on described substituted aryl to be carbon number be 5 ~ 6 alkyl, carbon number be the alkoxy or halogen of 3 ~ 6.
As preferably, described N-aryl N-alkylsulfonyl acrylamides and the feed ratio of arylsulfonyl hydrazine are 1:1 ~ 5; More preferably 1:1 ~ 2.
Find through experiment, the catalyzer adopted in the present invention can be only elemental copper, cupric oxide, mantoquita or cuprous salt; As preferably, described catalyzer is copper trifluoromethanesulfcomposite, neutralized verdigris, cuprous iodide, cuprous bromide, cupric chloride, cuprous chloride, cupric oxide, copper sulfate or copper powder; More preferably copper trifluoromethanesulfcomposite, neutralized verdigris, cuprous iodide, cuprous bromide, cupric chloride or cuprous chloride.
As preferably, described oxygenant is tertbutyl peroxide, benzoyl peroxide, peroxidized t-butyl perbenzoate, hydrogen peroxide, fluorine reagent, oxygen or Potassium Persulphate; More preferably tertbutyl peroxide, benzoyl peroxide or peroxidized t-butyl perbenzoate.
As preferably, the mass ratio of described N-aryl N-alkylsulfonyl acrylamides and oxygenant is 1:1 ~ 10; More preferably 1:1 ~ 5.
As preferably, described solvent is acetonitrile, methylene dichloride, Isosorbide-5-Nitrae-dioxane, chlorobenzene, toluene, 1,2-ethylene dichloride, fluorobenzene, ethyl acetate, Nitromethane 99Min., oil of mirbane or ether; More preferably acetonitrile, methylene dichloride, Isosorbide-5-Nitrae-dioxane, chlorobenzene, toluene, 1,2-ethylene dichloride or fluorobenzene.
As preferably, described temperature of reaction is 20 ~ 110 DEG C, and the reaction times is 2 ~ 5h; Temperature of reaction more preferably 80 ~ 100 DEG C.
Under above-mentioned preferred temperature of reaction, further preferably:
Described N-aryl N-alkylsulfonyl acrylamides is N-phenyl sulfonyl acrylamide, and arylsulfonyl hydrazine is to Methyl benzenesulfonyl hydrazine or to chlorobenzenesulfonyl hydrazine;
Described N-phenyl sulfonyl acrylamide and the mol ratio of arylsulfonyl hydrazine are 1:1.2 ~ 2;
Described catalyzer is copper trifluoromethanesulfcomposite.
In order to the universality of confirmatory reaction, carry out the effect of observing response by adding different additives, as preferably, described additive: sodium bicarbonate, sodium carbonate, sodium sulfate, sodium pyrosulfate, L-PROLINE.In reaction of the present invention, additionally can add additive, it is simple that demonstration is reacted, and easy handling, finally change temperature and the reaction times of reaction.
Compared with prior art, tool of the present invention has the following advantages:
Propose a kind of new reaction principle in the present invention in order to synthesize alpha-aromatic-'Beta '-sulfonyl acid amides, do not need the transition-metal catalyst adopting cost higher, and synthesis technique is simple, easy handling, convenient post-treatment, meets industrialized production.
Embodiment
Below in conjunction with specific embodiment, the present invention is described in further detail.
Embodiment 1
By N-phenyl sulfonyl acrylamide be 1:1.2 to the mol ratio of Methyl benzenesulfonyl hydrazine, with acetonitrile as solvent, the consumption of oxygenant tertbutyl peroxide is the mol ratio of N-phenyl N-alkylsulfonyl acrylamide is 2 times.
In round-bottomed flask, add N-phenylSulphon hydrazine acrylamide 4.7g, to Methyl benzenesulfonyl hydrazine 3.4g, add copper trifluoromethanesulfcomposite 1.1g, add oxygenant tertbutyl peroxide 3.9g after dissolving with acetonitrile, above-mentioned solution is reacted 3 hours at 80 DEG C.
Concrete reaction formula is as follows:
After having reacted, product column chromatographic isolation and purification is obtained corresponding α-phenyl-β-to Methyl benzenesulfonyl base acid amides.Obtaining corresponding fusing point is 177 DEG C, and yield is 87%.
1H?NMR(500MHz,CDCl
3)δ7.52(d,J＝8.3Hz,2H),7.31(d,J＝7.5Hz,2H),7.26(t,J＝8.1Hz,3H),7.17(dd,J＝13.4,8.2Hz,4H),7.07(dd,J＝15.4,7.8Hz,3H),4.13(d,J＝14.9Hz,1H),3.82(d,J＝14.9Hz,1H),2.39(s,3H),2.32(s,3H),2.10(s,3H).
13C?NMR(125MHz,CDCl
3)δ172.9,144.0,138.2,138.0,137.4,136.4,129.6,129.5,128.9,127.6,127.0,124.7,120.1,64.1,50.1,22.7,21.6,21.0.
Embodiment 2
By N-phenylSulphon hydrazine acrylamide be 1:1.5 to the mol ratio of Methyl benzenesulfonyl hydrazine, in flask, add raw material add N-phenylSulphon hydrazine acrylamide 4.7g, to Methyl benzenesulfonyl hydrazine 4.2g, add copper trifluoromethanesulfcomposite 1.1g, add oxygenant tertbutyl peroxide 3.9g after after dissolving with acetonitrile, other operations are with embodiment 1.
After having reacted, product column chromatographic isolation and purification is obtained corresponding α-phenyl-β-to Methyl benzenesulfonyl base acid amides.Obtaining corresponding fusing point is 177 °, and yield is 84%.
Embodiment 3
By N-phenyl N-sulfonyl hydrazide acrylamide be 1:2 to the mol ratio of Methyl benzenesulfonyl hydrazine, in flask, add raw material add N-phenyl N-sulfonyl hydrazide acrylamide 4.7g, to Methyl benzenesulfonyl hydrazine 5.6g, add copper trifluoromethanesulfcomposite 1.1g, add oxygenant tertbutyl peroxide 3.9g after after dissolving with acetonitrile, other operations are with embodiment 1
After having reacted, product column chromatographic isolation and purification is obtained corresponding α-phenyl-β-to Methyl benzenesulfonyl base acid amides.Obtaining corresponding fusing point is 177 °, and yield is 80%.
Embodiment 4
Be 1:4 by the mol ratio of N-phenyl N-sulfonyl hydrazide acrylamide and tertbutyl peroxide, in flask, add raw material add N-phenylSulphon hydrazine acrylamide 4.7g, to Methyl benzenesulfonyl hydrazine 3.4g, add copper trifluoromethanesulfcomposite 1.1g, add oxygenant tertbutyl peroxide 7.7g after after dissolving with acetonitrile, other operations are with embodiment 1
After having reacted, product column chromatographic isolation and purification is obtained corresponding α-phenyl-β-to Methyl benzenesulfonyl base acid amides.Obtaining corresponding fusing point is 177 °, and yield is 88%.
Embodiment 5
Catalysts is neutralized verdigris, adds 0.6g.Other operations are with example 1.
After having reacted, product column chromatographic isolation and purification is obtained corresponding α-phenyl-β-to Methyl benzenesulfonyl base acid amides.Obtaining corresponding fusing point is 177 °, and yield is 73%.
Embodiment 6
Catalysts is cuprous iodide, adds 0.6g.Other operations are with example 1.
After having reacted, product column chromatographic isolation and purification is obtained corresponding α-phenyl-β-to Methyl benzenesulfonyl base acid amides.Obtaining corresponding fusing point is 177 °, and yield is 78%.
Embodiment 7
Catalysts is cuprous bromide, adds 0.4g.Other operations are with example 1.
After having reacted, product column chromatographic isolation and purification is obtained corresponding α-phenyl-β-to Methyl benzenesulfonyl base acid amides.Obtaining corresponding fusing point is 177 °, and yield is 80%.
Embodiment 8
Catalysts is cupric chloride, adds 0.4g.Other operations are with example 1.
After having reacted, product column chromatographic isolation and purification is obtained corresponding α-phenyl-β-to Methyl benzenesulfonyl base acid amides.Obtaining corresponding fusing point is 177 °, and yield is 70%.
Embodiment 9
Catalysts is cuprous chloride, adds 0.3g.Other operations are with example 1.
After having reacted, product column chromatographic isolation and purification is obtained corresponding α-phenyl-β-to Methyl benzenesulfonyl base acid amides.Obtaining corresponding fusing point is 177 °, and yield is 68%.
Embodiment 10
Catalysts is Anhydrous Ferric Chloride, adds 0.4g.Other operations are with example 1.
After having reacted, by tlc analysis, do not obtain product.
Embodiment 11
Catalysts is tetrabutylammonium iodide, adds 0.8g.Other operations are with example 1.
After having reacted, product column chromatographic isolation and purification is obtained corresponding α-phenyl-β-to Methyl benzenesulfonyl base acid amides.Obtaining corresponding fusing point is 177 °, and yield is 12%.
Embodiment 12
Reaction solvent is Isosorbide-5-Nitrae-dioxane, and other operations are with example 1.
After having reacted, product column chromatographic isolation and purification is obtained corresponding α-phenyl-β-to Methyl benzenesulfonyl base acid amides.Obtaining corresponding fusing point is 177 °, and yield is 72%.
Embodiment 13
Reaction solvent is chlorobenzene, and other operations are with example 1.
After having reacted, product column chromatographic isolation and purification is obtained corresponding α-phenyl-β-to Methyl benzenesulfonyl base acid amides.Obtaining corresponding fusing point is 177 °, and yield is 77%.
Embodiment 14
Reaction solvent is toluene, and other operations are with example 1.
After having reacted, product column chromatographic isolation and purification is obtained corresponding α-phenyl-β-to Methyl benzenesulfonyl base acid amides.Obtaining corresponding fusing point is 177 °, and yield is 80%.
Embodiment 15
Reaction solvent is methylene dichloride, and other operations are with example 1.
After having reacted, product column chromatographic isolation and purification is obtained corresponding α-phenyl-β-to Methyl benzenesulfonyl base acid amides.Obtaining corresponding fusing point is 177 °, and yield is 82%.
Embodiment 16
Reaction solvent is 1.2-ethylene dichloride, and other operations are with example 1.
After having reacted, product column chromatographic isolation and purification is obtained corresponding α-phenyl-β-to Methyl benzenesulfonyl base acid amides.Obtaining corresponding fusing point is 177 °, and yield is 66%.
Embodiment 17
Reaction oxygenant is benzoyl peroxide 5.8g, and other operations are with example 1.
After having reacted, product column chromatographic isolation and purification is obtained corresponding α-phenyl-β-to Methyl benzenesulfonyl base acid amides.Obtaining corresponding fusing point is 177 °, and yield is 82%.
Embodiment 18
Reaction oxygenant is peroxidized t-butyl perbenzoate 12.1g, and other operations are with example 1.
After having reacted, product column chromatographic isolation and purification is obtained corresponding α-phenyl-β-to Methyl benzenesulfonyl base acid amides.Obtaining corresponding fusing point is 177 °, and yield is 83%.
Embodiment 19
Reaction oxygenant is hydrogen peroxide 0.8g, and other operations are with example 1.
After having reacted, product column chromatographic isolation and purification is obtained corresponding α-phenyl-β-to Methyl benzenesulfonyl base acid amides.Obtaining corresponding fusing point is 177 °, and yield is 43%.
Embodiment 20
Reaction oxygenant is Potassium Persulphate 6.5g, and other operations are with example 1.
After having reacted, product column chromatographic isolation and purification is obtained corresponding α-phenyl-β-to Methyl benzenesulfonyl base acid amides.Obtaining corresponding fusing point is 177 °, and yield is 22%.
Embodiment 21
Be 1:1.2 by the feed ratio of N-phenylSulphon hydrazine acrylamide and sulfonyl hydrazide, with acetonitrile as solvent, the consumption of oxygenant tertbutyl peroxide is 2 times of N-phenylSulphon hydrazine acrylamide.
In round-bottomed flask, add raw material add N-phenylSulphon hydrazine acrylamide 4.7g, to Methyl benzenesulfonyl hydrazine 3.4g, add copper trifluoromethanesulfcomposite 1.1g, add additive sodium bicarbonate 3.7g, add oxygenant tertbutyl peroxide 3.9g after after dissolving with acetonitrile, above-mentioned solvent is reacted 3 hours at 80 DEG C.
After having reacted, product column chromatographic isolation and purification is obtained corresponding α-phenyl-β-to Methyl benzenesulfonyl base acid amides.Obtaining corresponding fusing point is 177 °, and yield is 66%.
Embodiment 22
Reaction additives is L-PROLINE 0.3g, and other operations are with example 17.
After having reacted, product column chromatographic isolation and purification is obtained corresponding α-phenyl-β-to Methyl benzenesulfonyl base acid amides.Obtaining corresponding fusing point is 177 °, and yield is 85%.
Embodiment 23
Reaction is reacted at normal temperatures, and other operations are with example 1.
After having reacted, product column chromatographic isolation and purification is obtained corresponding α-phenyl-β-to Methyl benzenesulfonyl base acid amides.Obtaining corresponding fusing point is 177 °, and yield is 55%.
Embodiment 24
Reaction is at 100 DEG C, and other operations are with example 1.
After having reacted, product column chromatographic isolation and purification is obtained corresponding α-phenyl-β-to Methyl benzenesulfonyl base acid amides.Obtaining corresponding fusing point is 177 °, and yield is 88%.
Embodiment 25
Reaction times is 5 hours, and other operations are with example 1.
After having reacted, product column chromatographic isolation and purification is obtained corresponding α-phenyl-β-to Methyl benzenesulfonyl base acid amides.Obtaining corresponding fusing point is 177 °, and yield is 86%.
Embodiment 26
By N-phenyl N-alkylsulfonyl acrylamide be 1:1.2 to the mol ratio of chlorobenzenesulfonyl hydrazine, with acetonitrile as solvent, the consumption of oxygenant tertbutyl peroxide is the mol ratio of N-phenyl N-alkylsulfonyl acrylamide is 2 times.
In round-bottomed flask, add N-phenylSulphon hydrazine acrylamide 4.7g, to chlorobenzenesulfonyl hydrazine 3.7g, add copper trifluoromethanesulfcomposite 1.1g, add oxygenant tertbutyl peroxide 3.9g after after dissolving with acetonitrile, above-mentioned solvent is reacted 3 hours at 80 DEG C.
Concrete reaction formula is as follows:
After having reacted, product column chromatographic isolation and purification is obtained corresponding α-phenyl-β-to chlorobenzenesulfonyl acid amides.By high resolution detection, obtain 413.0855, yield is 80%.
Embodiment 27
Be 1:1.2 by the mol ratio of N-phenyl N-alkylsulfonyl acrylamide and benzol sulfohydrazide, with acetonitrile as solvent, the consumption of oxygenant tertbutyl peroxide is the mol ratio of N-phenyl N-alkylsulfonyl acrylamide is 2 times.
In round-bottomed flask, add N-phenylSulphon hydrazine acrylamide 4.7g, benzol sulfohydrazide 3.1g, add copper trifluoromethanesulfcomposite 1.1g, add oxygenant tertbutyl peroxide 3.9g after after dissolving with acetonitrile, above-mentioned solvent is reacted 3 hours at 80 DEG C.
Concrete reaction formula is as follows:
After having reacted, product column chromatographic isolation and purification is obtained corresponding α-phenyl-β-benzenesulfonyl acid amides.By high resolution detection, obtain 379.1244, yield is 88%.
Claims (8)
1. synthesize a method for alpha-aromatic-'Beta '-sulfonyl acid amides, it is characterized in that, synthesis step is as follows:
By N-aryl N-alkylsulfonyl acrylamides, arylsulfonyl hydrazine, catalyzer and oxygenant and solvent, at 0 ~ 150 DEG C, react 1 ~ 10h, after having reacted, obtain described alpha-aromatic-'Beta '-sulfonyl amide compound through separation and purification;
The structural formula of described N-aryl N-alkylsulfonyl acrylamides as shown in formula I,
The structural formula of described arylsulfonyl hydrazine is as shown in formula II;
The structural formula of described alpha-aromatic-'Beta '-sulfonyl amide compound is as shown in formula III;
In formula, Ar
1, Ar
2and Ar
3independently selected from aryl or substituted aryl, the substituting group on described substituted aryl to be carbon number be 5 ~ 6 alkyl, carbon number be the alkoxy or halogen of 3 ~ 6.
2. the method for synthesis alpha-aromatic-'Beta '-sulfonyl acid amides according to claim 1, is characterized in that, described N-aryl N-alkylsulfonyl acrylamides and the mol ratio of arylsulfonyl hydrazine are 1:1 ~ 5.
3. the method for synthesis alpha-aromatic-'Beta '-sulfonyl acid amides according to claim 1, is characterized in that, described catalyzer is elemental copper, cupric oxide, cuprous salt or mantoquita.
4. the method for synthesis alpha-aromatic-'Beta '-sulfonyl acid amides according to claim 3; it is characterized in that, described catalyzer is copper trifluoromethanesulfcomposite, neutralized verdigris, cuprous iodide, cuprous bromide, cupric chloride, cuprous chloride, cupric oxide, copper sulfate or copper powder.
5. the method for synthesis alpha-aromatic-'Beta '-sulfonyl acid amides according to claim 1; it is characterized in that, described oxygenant is tertbutyl peroxide, benzoyl peroxide, peroxidized t-butyl perbenzoate, hydrogen peroxide, fluorine reagent, oxygen or Potassium Persulphate.
6. the method for synthesis alpha-aromatic-'Beta '-sulfonyl acid amides according to claim 5, is characterized in that, the mol ratio of described N-aryl N-alkylsulfonyl acrylamides and oxygenant is 1:1 ~ 10.
7. the method for synthesis alpha-aromatic-'Beta '-sulfonyl acid amides according to claim 1; it is characterized in that; described solvent is acetonitrile, methylene dichloride, Isosorbide-5-Nitrae-dioxane, chlorobenzene, toluene, 1,2-ethylene dichloride, fluorobenzene, ethyl acetate, Nitromethane 99Min., oil of mirbane or ether.
8. the method for synthesis alpha-aromatic-'Beta '-sulfonyl acid amides according to claim 1, is characterized in that, described temperature of reaction is 20 ~ 110 DEG C, and the reaction times is 2 ~ 5h.
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104592086A (en) * | 2015-01-31 | 2015-05-06 | 台州学院 | Method for preparing indole compound through copper salt catalysis |
| CN105061252A (en) * | 2015-07-21 | 2015-11-18 | 安徽理工大学 | Method for preparing 1,2-bis(1-aralkyl methylene) hydrazine compound |
| CN105669491A (en) * | 2016-03-14 | 2016-06-15 | 苏州大学 | Acidylation method of amine |
| CN106432004A (en) * | 2016-09-28 | 2017-02-22 | 济南大学 | Synthesizing method of 3-sulfonyl alcohol compounds |
| CN106432003A (en) * | 2016-09-21 | 2017-02-22 | 济南大学 | Method for synthesizing 3-sulfonyl nitrile compound |
| CN106631927A (en) * | 2016-11-24 | 2017-05-10 | 济南大学 | Synthesis method of 3-sulfonyl propionic acid compound |
| CN108558734A (en) * | 2018-05-07 | 2018-09-21 | 江西师范大学 | Method for synthesizing 2-aryl-3-arylsulfonyl-1H-indole under catalysis of copper |
-
2014
- 2014-08-29 CN CN201410439158.9A patent/CN104262213A/en active Pending
Non-Patent Citations (1)
| Title |
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| QINGSHAN TIAN, ET AL.: "Copper-catalyzed arylsulfonylation of N-arylsulfonyl-acrylamides with arylsulfonohydrazides: synthesis of sulfonated oxindoles", 《ORGANIC & BIOMOLECULAR CHEMISTRY》 * |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104592086A (en) * | 2015-01-31 | 2015-05-06 | 台州学院 | Method for preparing indole compound through copper salt catalysis |
| CN104592086B (en) * | 2015-01-31 | 2017-06-06 | 台州学院 | A kind of method that Benzazole compounds are prepared by mantoquita catalysis |
| CN105061252A (en) * | 2015-07-21 | 2015-11-18 | 安徽理工大学 | Method for preparing 1,2-bis(1-aralkyl methylene) hydrazine compound |
| CN105061252B (en) * | 2015-07-21 | 2017-05-31 | 安徽理工大学 | One kind prepares 1,2 pairs of methods of (1 aralkyl methylene) hydrazine compound |
| CN105669491A (en) * | 2016-03-14 | 2016-06-15 | 苏州大学 | Acidylation method of amine |
| CN105669491B (en) * | 2016-03-14 | 2017-10-13 | 苏州大学 | A kind of acylation method of amine |
| CN106432003A (en) * | 2016-09-21 | 2017-02-22 | 济南大学 | Method for synthesizing 3-sulfonyl nitrile compound |
| CN106432004A (en) * | 2016-09-28 | 2017-02-22 | 济南大学 | Synthesizing method of 3-sulfonyl alcohol compounds |
| CN106432004B (en) * | 2016-09-28 | 2018-08-28 | 济南大学 | A kind of synthetic method of 3- sulfuryls alcohol compound |
| CN106631927A (en) * | 2016-11-24 | 2017-05-10 | 济南大学 | Synthesis method of 3-sulfonyl propionic acid compound |
| CN108558734A (en) * | 2018-05-07 | 2018-09-21 | 江西师范大学 | Method for synthesizing 2-aryl-3-arylsulfonyl-1H-indole under catalysis of copper |
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