CN107814757A - A kind of method for synthesizing polysubstituted pyrrole derivative - Google Patents
A kind of method for synthesizing polysubstituted pyrrole derivative Download PDFInfo
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- CN107814757A CN107814757A CN201711107817.9A CN201711107817A CN107814757A CN 107814757 A CN107814757 A CN 107814757A CN 201711107817 A CN201711107817 A CN 201711107817A CN 107814757 A CN107814757 A CN 107814757A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
- C07D207/416—2,5-Pyrrolidine-diones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/333—Radicals substituted by oxygen or sulfur atoms
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Abstract
The present invention is a kind of synthetic method of polysubstituted pyrrole derivative, the synthetic method is with 1 shown in β nitrostyrolenes shown in primary aromatic amine derivative shown in Formula II, formula III and its derivative, formula IV, 3 dicarbonyl compounds are raw material, using LAuCl and AgOTf as catalyst, polysubstituted pyrrole derivative described in production I is reacted at 20 DEG C -50 DEG C.The inventive method is preferred by being carried out to catalyst, realize polysubstituted pyrrole derivative to react under relatively low or even normal temperature, product yield high, there is very strong practicality, easily-controlled reaction conditions and easily realize, the synthesis of polysubstituted pyrrole derivative is carried out under safer environment.
Description
Technical field
The present invention relates to a kind of synthetic method of derivative, particularly a kind of method for synthesizing polysubstituted pyrrole derivative.
Background technology
Pyrroles and its homologue are primarily present in Dippel's oil, are measured present in coal tar seldom.Pyrroles can be by Dippel's oil
Fractionation obtains；Or handled with diluted alkaline, then purified with acid acidifying aftercut.It is the five-ring heterocycles chemical combination containing a nitrogen heteroatom
Thing, its molecular formula are C4H5N。
Azole derivatives have extensive antitumor, anti-inflammatory, antibacterial etc. effect, and therefore, it is studied always by people institute
Pay attention to.In the prior art, synthesis polysubstituted pyrrole derivative is all carried out at high temperature, and in general synthesis temperature is all at 80 DEG C
More than, majority has all reached 100 DEG C, or even has up to 150 DEG C.Such as Li Baole " multicomponent one pot process azole derivatives "
（Hebei Normal University's Master's thesis）Nitroolefin, amine and the component one pot process of 1,3- dicarbonyl compound three is disclosed to take more
For azole derivatives, catalyst is that magnetic Nano material loads antimony trioxide used by synthesis, and the synthesis is exactly at 80 DEG C
Carry out, yield can reach 80%, and when synthesis temperature is down to 60 DEG C, yield only has 50% or so.Pyroreaction not only makes conjunction
Greatly improved into cost, while also increase the security risks of reaction.
The content of the invention
The technical problems to be solved by the invention are in view of the shortcomings of the prior art, there is provided a kind of polysubstituted pyrrole of new synthesis
The method for coughing up derivative, the synthetic method use new catalyst, reacted at a lower temperature on the premise of yield is ensured,
Synthetic reaction operation is safer.
The technical problems to be solved by the invention are realized by following technical scheme.The present invention is that one kind takes more
For the synthetic method of azole derivatives, be characterized in, the structure of described polysubstituted pyrrole derivative as described in Formulas I,
I
In Formulas I：
R substituted radicals are selected from hydrogen, alkyl, aryl；
R1 、R2Substituted radical is selected from hydrogen, halogen, alkyl, alkoxy, aryl；
R3 Substituted radical is selected from alkyl, alkoxy, aryl amine；
The synthetic method is with beta-nitrostyrene shown in primary aromatic amine derivative shown in Formula II, formula III and its derivative, formula IV
Shown 1,3- dicarbonyl compounds are raw material, and using LAuCl and AgOTf as catalyst, production I institutes are reacted at 20 DEG C -50 DEG C
State polysubstituted pyrrole derivative；It is comprised the following steps that：
（1）In reaction vessel, appropriate catalyst LAuCl and AgOTf are added, adds appropriate reaction dissolvent, room temperature is stirred
Mix, it is 0.8-1.1 to sequentially add material molar ratio：0.9-1.2：Primary aromatic amine derivative shown in 1 Formula II, formula III institute
Show 1,3- dicarbonyl compounds shown in beta-nitrostyrene and its derivative, formula IV, reactant mixture is placed at 20 DEG C -50 DEG C
Reaction, it is complete to TLC detection reactions；
L in LAuCl is part, selected from triphenylphosphine, BTA, 2- (di-t-butyl phosphine) biphenyl or 2- dicyclohexyls
Phosphorus -2,4,6- tri isopropyl biphenyls；
II
III
IV
（2）It is concentrated under reduced pressure after dry reaction solution, addition saturated aqueous sodium carbonate is appropriate, is extracted with ethyl acetate, is associated with
Machine phase, with saturated common salt water washing；Anhydrous sodium sulfate drying is used after liquid separation, filters, organic solvent is removed under reduced pressure, using silicagel column
Chromatography purifies, and obtains target product i.e. polysubstituted pyrrole derivative.
The synthetic route of the inventive method is as follows：
A kind of synthetic method of polysubstituted pyrrole derivative of the present invention, its further preferred technical scheme are：Raw material
Primary aromatic amine derivative shown in Formula II, 1,3- dicarbapentaborane shown in beta-nitrostyrene shown in formula III and its derivative, formula IV
The mol ratio of compound is 1：1.1：1.1.
A kind of synthetic method of polysubstituted pyrrole derivative of the present invention, its further preferred technical scheme are：
Primary aromatic amine derivative shown in Formula II is aniline, and beta-nitrostyrene shown in formula III and its derivative are nitrostyrolene；Formula
1,3- dicarbonyl compounds shown in IV is 3- oxo-N-phenyl butyramides；
A kind of synthetic method of polysubstituted pyrrole derivative of the present invention, its further preferred technical scheme are：It is described
Reaction dissolvent in methanol, ethanol, isopropanol, ethyl acetate, acetonitrile, toluene, dichloromethane, methyl tertiary butyl ether(MTBE) one
Kind is several.
A kind of synthetic method of polysubstituted pyrrole derivative of the present invention, its further preferred technical scheme are：
Reactant mixture, which is placed at 20 DEG C -30 DEG C, to react, using alcohols as reaction dissolvent.Methanol most preferably therein, ethanol,
Isopropanol.Alcohols reaction dissolvent has carried out important effect to synthetic method of the present invention.
Compared with prior art, synthetic method of the present invention has advantages below：Synthetic method of the present invention is with fragrant shown in Formula II
1,3- dicarbonyl compounds shown in beta-nitrostyrene shown in fragrant race's primary amine derivatives, formula III and its derivative, formula IV are original
Material, using LAuCl and AgOTf as catalyst, polysubstituted pyrrole derivative described in production I is reacted at 20 DEG C -50 DEG C.This hair
Bright method is preferred by being carried out to catalyst, realizes polysubstituted pyrrole derivative and is reacted under relatively low or even normal temperature, reach compared with
High yield.With very strong practicality, easily-controlled reaction conditions and easily realize, greatly save synthesis cost, also make
The synthesis of polysubstituted pyrrole derivative is carried out under safer environment.
Brief description of the drawings
Fig. 1 is the single crystal diffraction figure of polysubstituted pyrrole derivative made from embodiment 6.
Embodiment
Concrete technical scheme of the invention described further below, in order to which those skilled in the art is further understood that
The present invention, without forming the limitation to its right.
Embodiment 1, a kind of synthetic method of polysubstituted pyrrole derivative, the structure of described polysubstituted pyrrole derivative is such as
Described in Formulas I, in Formulas I：
R substituted radicals are selected from hydrogen, alkyl, aryl；
R1 、R2Substituted radical is selected from hydrogen, halogen, alkyl, alkoxy, aryl；
R3 Substituted radical is selected from alkyl, alkoxy, aryl amine；
The synthetic method is with beta-nitrostyrene shown in primary aromatic amine derivative shown in Formula II, formula III and its derivative, formula IV
Shown 1,3- dicarbonyl compounds are raw material, using LAuCl and AgOTf as catalyst, react described in production I more at 20 DEG C and take
For azole derivatives；It is comprised the following steps that：
（1）In reaction vessel, appropriate catalyst LAuCl and AgOTf are added, adds appropriate reaction dissolvent, room temperature is stirred
Mix, sequentially add material molar ratio as 0.8：0.9：Primary aromatic amine derivative shown in 1 Formula II, β-nitrobenzene shown in formula III
1,3- dicarbonyl compounds shown in ethene and its derivative, formula IV, reactant mixture, which is placed at 20 DEG C, to react, anti-to TLC detections
Should be complete；
L in LAuCl is part, is triphenylphosphine；
（2）It is concentrated under reduced pressure after dry reaction solution, addition saturated aqueous sodium carbonate is appropriate, is extracted with ethyl acetate, is associated with
Machine phase, with saturated common salt water washing；Anhydrous sodium sulfate drying is used after liquid separation, filters, organic solvent is removed under reduced pressure, using silicagel column
Chromatography purifies, and produces target product i.e. polysubstituted pyrrole derivative.
Described reaction dissolvent is selected from methanol, ethanol or isopropanol.
Embodiment 2, a kind of synthetic method of polysubstituted pyrrole derivative, the synthetic method is with primary aromatic amine shown in Formula II
1,3- dicarbonyl compounds are raw material shown in beta-nitrostyrene shown in derivative, formula III and its derivative, formula IV, with LAuCl
It is catalyst with AgOTf, polysubstituted pyrrole derivative described in production I is reacted at 50 DEG C；In its specific steps：Shown in Formula II
1,3- dicarbonyl compounds rubs shown in beta-nitrostyrene shown in primary aromatic amine derivative, formula III and its derivative, formula IV
You are than being 1.1：1.2：L in 1, LAuCl is part, is 2- (di-t-butyl phosphine) biphenyl or 2- dicyclohexyl phosphorus -2,4,6-
Tri isopropyl biphenyl；Described reaction dissolvent is ethyl acetate, acetonitrile or toluene.Remaining is same as Example 1.
Embodiment 3, a kind of synthetic method of polysubstituted pyrrole derivative, the synthetic method is with primary aromatic amine shown in Formula II
1,3- dicarbonyl compounds are raw material shown in beta-nitrostyrene shown in derivative, formula III and its derivative, formula IV, with LAuCl
It is catalyst with AgOTf, polysubstituted pyrrole derivative described in production I is reacted at 30 DEG C；In its specific steps：Shown in Formula II
1,3- dicarbonyl compounds rubs shown in beta-nitrostyrene shown in primary aromatic amine derivative, formula III and its derivative, formula IV
You are than being 0.9：1.1：L in 1, LAuCl is part, is BTA；Described reaction dissolvent is dichloromethane or first
Base tertbutyl ether；Remaining is same as Example 1.
Embodiment 4, a kind of synthetic method of polysubstituted pyrrole derivative, the synthetic method is with primary aromatic amine shown in Formula II
1,3- dicarbonyl compounds are raw material shown in beta-nitrostyrene shown in derivative, formula III and its derivative, formula IV, with LAuCl
It is catalyst with AgOTf, polysubstituted pyrrole derivative described in production I is reacted at 25 DEG C；In its specific steps：Shown in Formula II
1,3- dicarbonyl compounds rubs shown in beta-nitrostyrene shown in primary aromatic amine derivative, formula III and its derivative, formula IV
You are than being 1：1.1：1.1；L in LAuCl is part, is triphenylphosphine；Described reaction dissolvent is methanol；Remaining and embodiment
1 is identical.
Embodiment 5, a kind of synthetic method of polysubstituted pyrrole derivative, the synthetic method is with primary aromatic amine shown in Formula II
1,3- dicarbonyl compounds are raw material shown in beta-nitrostyrene shown in derivative, formula III and its derivative, formula IV, with LAuCl
It is catalyst with AgOTf, polysubstituted pyrrole derivative described in production I is reacted at 30 DEG C；In its specific steps：Shown in Formula II
1,3- dicarbonyl compounds rubs shown in beta-nitrostyrene shown in primary aromatic amine derivative, formula III and its derivative, formula IV
You are than being 0.8：0.95：L in 1, LAuCl is part, is 2- (di-t-butyl phosphine) biphenyl；Described reaction dissolvent be methanol with
The mixture of ethanol；Remaining is same as Example 1.
Embodiment 6, a kind of synthetic method experiment one of polysubstituted pyrrole derivative
In 25ml reaction bulb, Ph is added3PAuCl（20.0 mg, 0.04 mmol）And AgOTf（10.4 mg, 0.04
mmol）, 10ml ethanol is included in, after being stirred at room temperature 5 minutes, sequentially adds aniline（74.5mg, 0.80 mmol）, substitute nitro
Styrene（143.5 mg, 0.88 mmol）, 3- oxo-N-phenyl butyramides（155.9 mg, 0.88 mmol）.Reactant mixture
Room temperature reaction 6 hours is placed in, TLC detects complete to reaction.Carry out post processing purification：It is concentrated under reduced pressure after dry reaction solution, adds
Saturated aqueous sodium carbonate 20ml, uses ethyl acetate（10ml×3）Extraction, merge organic phase, use saturated aqueous common salt（10ml×1）
Washing.Anhydrous sodium sulfate drying is used after liquid separation, filters, organic solvent is removed under reduced pressure, using silica gel column chromatography separating purification, obtains
Clean product, white solid, yield 83%.Its reaction scheme is as follows：
The nucleus magnetic hydrogen spectrum and carbon modal data of the present embodiment synthetic product are as follows：
1H NMR (500 MHz, CDCl3) δ 7.58-7.36 (m, 10H), 7.31-7.30 (m, 4H), 7.09
(br, 1H), 6.80 (s, 1H), 2.52 (s, 3H)；
13C NMR (500 MHz, CDCl3) δ 163.94, 138.77, 138.22, 135.49, 133.36,
131.98, 130.70, 129.44, 128.97, 128.25, 126.25, 123.85, 122.37, 121.31,
120.31, 119.52, 115.36, 12.33。
Confirm that product made from the present embodiment is polysubstituted pyrrole derivative, its single crystal diffraction is such as
Shown in Fig. 1.
Embodiment 7, a kind of synthetic method experiment two of polysubstituted pyrrole derivative：
In 25ml reaction bulb, Ph is added3PAuCl（20.0 mg, 0.04 mmol）And AgOTf（10.4 mg, 0.04
mmol）, 10ml ethanol is included in, after being stirred at room temperature 5 minutes, sequentially adds o-aminoanisole（98.5mg, 0.80 mmol）,
Nitrostyrolene（131.3 mg, 0.88 mmol）, acetylacetone,2,4-pentanedione（88.1 mg, 0.88 mmol）.Reactant mixture is placed in 50 DEG C
Reaction 4 hours, TLC detect complete to reaction.Carry out post processing purification：It is concentrated under reduced pressure after dry reaction solution, adds unsaturated carbonate
Sodium water solution 20ml, uses ethyl acetate（10ml×3）Extraction, merge organic phase, use saturated aqueous common salt（10ml×1）Washing.Point
Anhydrous sodium sulfate drying is used after liquid, filters, organic solvent is removed under reduced pressure, using silica gel column chromatography separating purification, obtains pure production
Thing, white solid, yield 81%.Its reaction scheme is as follows
The nucleus magnetic hydrogen spectrum and carbon modal data of the product as white solid of the present embodiment synthesis are as follows：
1H NMR (500 MHz, CDCl3) δ7.46-7.38 (m, 5H), 7.32 (t, 1H, J = 5), 7.28 (t,
1H, J = 5), 7.07 (t, 2H, J = 5), 6.60 (s, 1H), 3.85 (s, 3H), 2.33 (s, 3H),
2.13 (s, 3H)；
13C NMR (126 MHz, CDCl3) δ 197.56, 154.77, 137.13, 136.35, 130.03, 129.46,
128.80, 128.19, 127.41, 126.64, 125.93, 121.60, 121.08, 120.79, 112.07,
55.71, 31.09, 12.46。
Embodiment 8, a kind of synthetic method experiment three of polysubstituted pyrrole derivative：
In 25ml reaction bulb, Ph is added3PAuCl（20.0 mg, 0.04 mmol）And AgOTf（10.4 mg, 0.04
mmol）, 10ml ethanol is included in, after being stirred at room temperature 5 minutes, sequentially adds aniline（74.5mg, 0.80 mmol）, substitute nitro
Styrene（161.5 mg, 0.88 mmol）, ethyl acetoacetate（114.5mg 0.88 mmol）.Reactant mixture is placed in 50 DEG C
Reaction 3 hours, TLC detect complete to reaction.Carry out post processing purification：It is concentrated under reduced pressure after dry reaction solution, adds unsaturated carbonate
Sodium water solution 20ml, uses ethyl acetate（10ml×3）Extraction, merge organic phase, use saturated aqueous common salt（10ml×1）Washing.Point
Anhydrous sodium sulfate drying is used after liquid, filters, organic solvent is removed under reduced pressure, using silica gel column chromatography separating purification, obtains pure production
Thing, white solid, yield 76%.Its reaction scheme is as follows:
The nucleus magnetic hydrogen spectrum and carbon modal data of the product as white solid of the present embodiment synthesis are as follows：
1H NMR (500 MHz, CDCl3) δ 7.53-7.50 (m, 2H), 7.47-7.43 (m, 2H), 7.39-7.36
(m, 3H), 7.27-7.25 (m, 2H), 6.72 (s, 1H), 4.13 (q, 2H, J = 5), 2.52 (s, 3H),
1.03 (t, 3H, J =5)
13C NMR (126 MHz, CDCl3) δ 165.58, 138.94, 136.09, 135.42, 134.55, 131.66,
129.35, 128.95, 128.07, 127.87, 126.32, 126.01, 123.39, 121.09, 112.95,
59.39, 13.80, 12.52。
Claims (5)
- A kind of 1. synthetic method of polysubstituted pyrrole derivative, it is characterised in that the structure of described polysubstituted pyrrole derivative As described in Formulas I,IIn Formulas I：R substituted radicals are selected from hydrogen, alkyl, aryl；R1 、R2Substituted radical is selected from hydrogen, halogen, alkyl, alkoxy, aryl；R3 Substituted radical is selected from alkyl, alkoxy, aryl amine；The synthetic method is with beta-nitrostyrene shown in primary aromatic amine derivative shown in Formula II, formula III and its derivative, formula IV Shown 1,3- dicarbonyl compounds are raw material, and using LAuCl and AgOTf as catalyst, production I institutes are reacted at 20 DEG C -50 DEG C State polysubstituted pyrrole derivative；It is comprised the following steps that：（1）In reaction vessel, appropriate catalyst LAuCl and AgOTf are added, adds appropriate reaction dissolvent, room temperature is stirred Mix, it is 0.8-1.1 to sequentially add material molar ratio：0.9-1.2：Primary aromatic amine derivative shown in 1 Formula II, formula III institute Show 1,3- dicarbonyl compounds shown in beta-nitrostyrene and its derivative, formula IV, reactant mixture is placed at 20 DEG C -50 DEG C Reaction, it is complete to TLC detection reactions；L in LAuCl is part, selected from triphenylphosphine, BTA, 2- (di-t-butyl phosphine) biphenyl or 2- dicyclohexyls Phosphorus -2,4,6- tri isopropyl biphenyls；II IIIIV（2）It is concentrated under reduced pressure after dry reaction solution, addition saturated aqueous sodium carbonate is appropriate, is extracted with ethyl acetate, is associated with Machine phase, with saturated common salt water washing；Anhydrous sodium sulfate drying is used after liquid separation, filters, organic solvent is removed under reduced pressure, using silicagel column Chromatography purifies, and obtains target product i.e. polysubstituted pyrrole derivative.
- A kind of 2. synthetic method of polysubstituted pyrrole derivative according to claim 1, it is characterised in that：Starting materials of formulae II institutes Show primary aromatic amine derivative, 1,3- dicarbonyl compounds shown in beta-nitrostyrene shown in formula III and its derivative, formula IV Mol ratio is 1：1.1：1.1.
- A kind of 3. synthetic method of polysubstituted pyrrole derivative according to claim 1, it is characterised in that：It is fragrant shown in Formula II Fragrant race's primary amine derivatives are aniline, and beta-nitrostyrene shown in formula III and its derivative are nitrostyrolene, 1,3- bis- shown in IV Carbonyls is 3- oxo-N-phenyl butyramides.
- A kind of 4. synthetic method of polysubstituted pyrrole derivative according to claim 1 or 2 or 3, it is characterised in that：It is described Reaction dissolvent in methanol, ethanol, isopropanol, ethyl acetate, acetonitrile, toluene, dichloromethane, methyl tertiary butyl ether(MTBE) one Kind is several.
- A kind of 5. synthetic method of polysubstituted pyrrole derivative according to claim 1 or 2 or 3, it is characterised in that：Reaction Mixture, which is placed at 20 DEG C -30 DEG C, to react.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113087649A (en) * | 2021-03-25 | 2021-07-09 | 南京医科大学康达学院 | Preparation method of dihydropyrrolone derivative |
| CN113943242A (en) * | 2021-12-08 | 2022-01-18 | 浙江工业大学 | Preparation method of polysubstituted pyrrole compound |
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| CN1039807A (en) * | 1987-07-29 | 1990-02-21 | 美国氰胺公司 | Desinsection, kill mite, nematocides aryl-pyrrolidine and preparation method thereof |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113087649A (en) * | 2021-03-25 | 2021-07-09 | 南京医科大学康达学院 | Preparation method of dihydropyrrolone derivative |
| CN113087649B (en) * | 2021-03-25 | 2022-07-12 | 南京医科大学康达学院 | Preparation method of dihydropyrrolone derivative |
| CN113943242A (en) * | 2021-12-08 | 2022-01-18 | 浙江工业大学 | Preparation method of polysubstituted pyrrole compound |
| CN113943242B (en) * | 2021-12-08 | 2023-08-15 | 浙江工业大学 | Preparation method of polysubstituted pyrrole compound |
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