CN102408376A - Synthesis method of tetra-substituted iminazole - Google Patents
Synthesis method of tetra-substituted iminazole Download PDFInfo
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- CN102408376A CN102408376A CN2011103238821A CN201110323882A CN102408376A CN 102408376 A CN102408376 A CN 102408376A CN 2011103238821 A CN2011103238821 A CN 2011103238821A CN 201110323882 A CN201110323882 A CN 201110323882A CN 102408376 A CN102408376 A CN 102408376A
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- nitrine
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- thiazolinyl
- nitrone
- magnesium sulfate
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- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical class C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 title abstract 3
- 238000001308 synthesis method Methods 0.000 title abstract 3
- -1 alkenyl azide Chemical class 0.000 claims abstract description 48
- 238000006243 chemical reaction Methods 0.000 claims abstract description 24
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 18
- SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 claims abstract description 15
- 238000004440 column chromatography Methods 0.000 claims abstract description 14
- 238000001816 cooling Methods 0.000 claims abstract description 14
- 239000003480 eluent Substances 0.000 claims abstract description 14
- 239000012046 mixed solvent Substances 0.000 claims abstract description 14
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000002994 raw material Substances 0.000 claims abstract description 8
- 239000002904 solvent Substances 0.000 claims abstract description 6
- 150000002460 imidazoles Chemical class 0.000 claims description 18
- 239000000126 substance Substances 0.000 claims description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 11
- 238000010025 steaming Methods 0.000 claims description 5
- 230000035484 reaction time Effects 0.000 claims description 2
- 230000009286 beneficial effect Effects 0.000 abstract description 2
- 239000003054 catalyst Substances 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 238000010828 elution Methods 0.000 abstract 2
- 239000012295 chemical reaction liquid Substances 0.000 abstract 1
- 238000001514 detection method Methods 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 239000003208 petroleum Substances 0.000 abstract 1
- 238000002390 rotary evaporation Methods 0.000 abstract 1
- 238000004809 thin layer chromatography Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 16
- 238000010438 heat treatment Methods 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- VTWKXBJHBHYJBI-UHFFFAOYSA-N n-benzylidenehydroxylamine Chemical compound ON=CC1=CC=CC=C1 VTWKXBJHBHYJBI-UHFFFAOYSA-N 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- 238000000816 matrix-assisted laser desorption--ionisation Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 2
- NHOWDZOIZKMVAI-UHFFFAOYSA-N (2-chlorophenyl)(4-chlorophenyl)pyrimidin-5-ylmethanol Chemical compound C=1N=CN=CC=1C(C=1C(=CC=CC=1)Cl)(O)C1=CC=C(Cl)C=C1 NHOWDZOIZKMVAI-UHFFFAOYSA-N 0.000 description 1
- 101100391174 Dictyostelium discoideum forC gene Proteins 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The invention discloses a synthesis method of tetra-substituted iminazole shown by a formula III. The method comprises the following steps of: reacting alkenyl azide shown by a formula I and nitrone shown by a formula II as raw materials in the presence of anhydrous magnesium sulfate as an accelerant and 1,2-dichloroethane as a solvent at 50-80 DEG C for 24-48 h, and performing TLC (thin-layer chromatography) detection until the alkenyl azide disappears; after the reaction is over, cooling and concentrating the reaction liquid, and performing column chromatography elution by taking a mixed solvent of petroleum ether and ethyl acetate at a volume ratio of 10:1 as an eluent; collecting the elution liquid of all monitored products; and performing rotary evaporation to remove the solvent to obtain the 1,2,4,5-tetra-substituted iminazole. The synthesis method disclosed by the invention has the beneficial effects of no catalyst used, mild reaction, high yield and good selectivity, is easy to operate and realizes convenient post-treatment.
Description
(1) technical field
The present invention relates to a kind of compound method of four substituted imidazoles.
(2) background technology
Imidazoles is one type of very important nitrogen heterocyclic, and application is all arranged in a lot of fields.For example, medical, natural product, polymkeric substance, carbenes and ionic liquid etc. are referring to (J.Med.Chem.1990,33,1330; J.Med.Chem.1998,41,4744; Macromolecules 2003,36, and 1047; Chem.Rev.1996,96,2239; Chem.Rev.2009,109; Chem.Rev.2002,102,3667.).
The method severe reaction conditions of the synthetic imdazole derivatives of tradition is used highly basic like reaction needed, or high temperature, or the sour by product of reaction generation etc., referring to (Chem.Ber.1953,86,88; Ber.Dtsch.Chem.Ges.1882,15,1268; F.Kunckell, Ber.Dtsch.Chem.Ges.1901,34,637.J.Org.Chem.1977,42,1153.).After mostly taked substitution reaction and catalytic cyclization reaction in the strategy of a series of synthetic imdazole derivatives of people exploitation.Yet these reaction needed use simple imidazoles to be starting raw material, or to be difficult to the synthetic reacting precursor be raw material, or have used poisonous and expensive reagent or metal catalyst.Therefore, it is particularly important to develop the method for preparing imdazole derivatives a kind of economy, easy.
(3) summary of the invention
The compound method that the purpose of this invention is to provide a kind of easy and simple to handle, reaction conditions is gentle, yield is high, selectivity is good four substituted imidazole compounds.
The technical scheme that the present invention adopts is following:
A kind of compound method of four substituted imidazole compounds shown in formula III, described method is to be that raw material is promotor and 1 at anhydrous magnesium sulfate suc as formula the thiazolinyl nitrine shown in the I, suc as formula the nitrone shown in the II, the 2-ethylene dichloride is that solvent exists down; Under 50～80 ℃ of conditions, react 24～48h, TLC detects until the thiazolinyl nitrine and disappears, after question response finishes; With the reaction solution cooling concentration, through with sherwood oil: the ETHYLE ACETATE volume ratio is that 10: 1 mixed solvent is as the column chromatography wash-out of eluent, the elutriant part of collecting all products that monitor; Revolve and get 1 after steaming desolventizes; 2,4,5-four substituted imidazoles; Described thiazolinyl nitrine: nitrone: anhydrous magnesium sulfate amount of substance ratio is 1: 1.5～3: 2～8; Described thiazolinyl nitrine: 1,2-ethylene dichloride amount of substance ratio is 1: 210～300, in formula I, formula II or the formula III, R
1For-C
6H
5Or-3,4,5-tri-MeOC
6H
2R
2For-CO
2Et; R
3For-C
6H
5Or-p-MeOC
6H
4R
4For-C
6H
5Or-p-ClC
6H
4,
A kind of compound method of four substituted imidazole compounds shown in formula III, described method is to be promotor and 1 suc as formula the thiazolinyl nitrine shown in the I, suc as formula the nitrone raw material shown in the II at anhydrous magnesium sulfate, the 2-ethylene dichloride is that solvent exists down; Under 66 ℃ of conditions, react 48h, TLC detects until the thiazolinyl nitrine and disappears, after question response finishes; With the reaction solution cooling concentration, through with sherwood oil: the ETHYLE ACETATE volume ratio is that 10: 1 mixed solvent is as the column chromatography wash-out of eluent, the elutriant part of collecting all products that monitor; Revolve and get 1 after steaming desolventizes; 2,4,5-four substituted imidazoles; Described thiazolinyl nitrine: nitrone: anhydrous magnesium sulfate amount of substance ratio is 1: 3: 4; Described thiazolinyl nitrine: 1,2-ethylene dichloride amount of substance ratio is 1: 210, in formula I, formula II or the formula III, R
1For-C
6H
5Or-3,4,5-tri-MeOC
6H
2R
2For-CO
2Et; R
3For-C
6H
5Or-p-MeOC
6H
4R
4For-C
6H
5Or-p-ClC
6H
4
Reaction formula of the present invention is following:
Concrete, will be suc as formula the thiazolinyl nitrine 0.3mmol shown in the I, suc as formula the nitrone 0.9mmol shown in the II, 1.2mmol anhydrous magnesium sulfate and amount of substance are 1 of 210 times of thiazolinyl nitrine; The 2-ethylene dichloride is a raw material, places the 50mL there-necked flask, stirring heating; At 66 ℃ of reaction 48h, TLC detects until the thiazolinyl nitrine and disappears, after question response finishes; Cooling concentration; With sherwood oil: the ETHYLE ACETATE volume ratio is that 10: 1 mixed solvent is that the column chromatography of eluent carries out wash-out, separates obtaining product four substituted imidazole compounds shown in formula III, and product is identified with nuclear magnetic resonance spectrum and mass spectrum.
Preferable reaction temperature of the present invention is 66 ℃.
The preferred reaction time of the present invention is 48h.
The preferred thiazolinyl nitrine of the present invention: nitrone: anhydrous magnesium sulfate amount of substance ratio is 1: 3: 4.
The preferred thiazolinyl nitrine of the present invention: 1,2-ethylene dichloride amount of substance ratio is 1: 210.
The invention has the beneficial effects as follows: easy and simple to handle, catalyst-free, reaction temperature and, high, good, the convenient post-treatment of selectivity of yield.
(4) embodiment
Below in conjunction with specific embodiment the present invention is described further, but protection scope of the present invention is not limited in this:
Embodiment 1: by phenyl thiazolinyl nitrine and phenyl nitrone preparation 1,2,4-triphenyl-5-ester group imidazoles
With phenyl thiazolinyl nitrine 65mg (0.30mmol), phenyl nitrone 177mg (0.90mmol), anhydrous magnesium sulfate 150mg (1.24mmol) and 1,2-ethylene dichloride 5mL places the 50mL there-necked flask; Stirring heating, at 66 ℃ of reaction 48h, TLC detects and disappears until phenyl thiazolinyl nitrine; After question response finishes; Cooling concentration, with enriched material with hexanaphthene: ETHYLE ACETATE (V/V) is that 10: 1 mixed solvent carries out column chromatography as eluent, collects the elutriant part of all products that monitor; Revolve and get product 106mg, yield 96% after steaming desolventizes.
White?solid，m.p.127～128℃；
1H?NMR(CDCl
3，500MHz)：δ7.87(d，J＝7.5Hz，2H)，7.47-7.36(m，8H)，7.34-7.19(m，5H)，4.05(q，J＝7.0Hz，2H)，0.96(t，J＝7.0Hz，3H)；
13C?NMR(CDCl
3，125MHz)：δ160.4，149.9，148.2，137.9，134.1，129.6，129.5，129.1，129.0，129.0，128.9，128.2，128.1，127.8，121.8，60.5，13.6；HRMS(MALDI)Calcd?for?C
24H
21N
2O
2(M+H)
+：369.1598；Found：369.1595
Embodiment 2 is by 3,4, and 5-trimethoxyphenyl thiazolinyl nitrine and phenyl nitrone prepare 1,2-phenylbenzene-4-3,4,5-trimethoxyphenyl-5-ester group imidazoles
With 3,4,5-trimethoxy thiazolinyl nitrine 92mg (0.30mmol), phenyl nitrone 177mg (0.90mmol); Anhydrous magnesium sulfate 150mg (1.24mmol), 1,2-ethylene dichloride 5mL places the 50mL there-necked flask; Stirring heating, at 66 ℃ of reaction 48h, TLC detects until 3,4; 5-trimethoxyphenyl thiazolinyl nitrine disappears, after question response finishes, cooling concentration, with enriched material with hexanaphthene: ETHYLE ACETATE (V/V) is that 10: 1 mixed solvent carries out column chromatography as eluent; The elutriant part of all products that collection monitors, revolve steam after desolventizing product 135mg, yield 98%.
White?solid，m.p.117-119℃；
1H?NMR(CDCl
3，500MHz)：δ7.46-7.38(m，5H)，7.31-7.19(m，5H)，7.18(s，2H)，4.02(q，J＝7.0Hz，2H)，3.93(s，6H)，3.89(s，3H)，0.92(t，J＝7.0Hz，3H)；
13C?NMR(CDCl
3，125MHz)：δ160.5，152.7，149.5，147.7，138.3，137.9，129.5，129.4，129.1，129.0，128.8，128.1，127.9，121.8，106.9，60.8，60.5，56.1，13.6；HRMS(MALDI)Calcd?forC
27H
27N
2O
5(M+H)
+：459.1914；Found：459.1916
Embodiment 3 is by phenyl thiazolinyl nitrine with to methoxyl group nitrone preparation 1,4-phenylbenzene-2-p-methoxyphenyl-5-ester group imidazoles
With phenyl thiazolinyl nitrine 65mg (0.30mmol), to methoxyl group nitrone 205mg (0.90mmol), anhydrous magnesium sulfate 150mg (1.24mmol); 1,2-ethylene dichloride 5mL places the 50mL there-necked flask; Stirring heating, at 66 ℃ of reaction 48h, TLC detects and disappears until phenyl thiazolinyl nitrine; After question response finishes, cooling concentration, with enriched material with hexanaphthene: ETHYLE ACETATE (V/V) is that 10: 1 mixed solvent is as the column chromatography wash-out of eluent; The elutriant part of all products that collection monitors, revolve steam after desolventizing product 117mg, yield 98%.
White?solid，m.p.143-144℃；
1H?NMR(CDCl
3，500MHz)：δ7.86(d，J＝7.5Hz，2H)，7.47-7.29(m，10H)，6.74(d，J＝9.0Hz，2H)，4.04(q，J＝7.0Hz，2H)，3.75(s，3H)，0.95(t，J＝7.0Hz，3H)；
13C?NMR(CDCl
3，125MHz)：δ160.4，160.2，149.9，148.2，138.1，134.2，130.5，129.5，129.0，128.8，128.2，128.1，127.7，122.1，121.5，113.6，60.4，55.2，13.6；HRMS(MALDI)Calcdfor?C
25H
23N
2O
3(M+H)
+：399.1703；Found：399.1710
Embodiment 4 prepares 1-rubigan-2 by phenyl thiazolinyl nitrine and rubigan nitrone imidazoles, 4-phenylbenzene-5-ester group imidazoles
With phenyl thiazolinyl nitrine 65mg (0.30mmol), rubigan nitrone 209mg (0.90mmol), anhydrous magnesium sulfate 150mg (1.24mmol); 1,2-ethylene dichloride 5mL places the 50mL there-necked flask; Stirring heating, at 66 ℃ of reaction 48h, TLC detects and disappears until phenyl thiazolinyl nitrine; After question response finishes, cooling concentration, with enriched material with hexanaphthene: ETHYLE ACETATE (V/V) is that 10: 1 mixed solvent is as the column chromatography wash-out of eluent; The elutriant part of all products that collection monitors, revolve steam after desolventizing product 114mg, yield 94%.
White?solid，m.p.151-153℃；
1H?MR(CDCl
3，500MHz)：δ7.84(d，J＝7.0Hz，2H)，7.48-7.36(m，7H)，7.33-7.20(m，5H)，4.07(q，J＝7.0Hz，2H)，1.01(t，J＝7.0Hz，3H)；
13C?MR(CDCl
3，125MHz)：δ160.3，150.0，148.5，136.4，134.9，133.9，129.5，129.5，129.3，129.2，129.2，128.3，127.8，121.6，60.7，13.6；HRMS(MALDI)Calcd?for?C
24H
20ClN
2O
2(M+H)
+：403.1208；Found：403.1205
Embodiment 5 is with phenyl thiazolinyl nitrine 65mg (0.30mmol), phenyl nitrone 177mg (0.90mmol), anhydrous magnesium sulfate 150mg (1.24mmol) and 1, and 2-ethylene dichloride 5mL places the 50mL there-necked flask; Stirring heating, at 66 ℃ of reaction 24h, TLC detects and disappears until phenyl thiazolinyl nitrine; After question response finished, cooling concentration was with the enriched material column chromatography; With hexanaphthene: ETHYLE ACETATE (V/V) be 10: 1 mixed solvent as eluent, collect the elutriant part of all products that monitor, revolve steam after desolventizing 1; 2,4-triphenyl-5-ester group imidazoles 74mg, yield 67%.
Embodiment 6 is with phenyl thiazolinyl nitrine 65mg (0.30mmol), phenyl nitrone 177mg (0.90mmol), anhydrous magnesium sulfate 150mg (1.24mmol) and 1, and 2-ethylene dichloride 5mL places the 50mL there-necked flask; Stirring heating, at 66 ℃ of reaction 36h, TLC detects and disappears until phenyl thiazolinyl nitrine; After question response finishes, cooling concentration, with enriched material with hexanaphthene: ETHYLE ACETATE (V/V) is that 10: 1 mixed solvent is as the column chromatography wash-out of eluent; The elutriant part of all products that collection monitors, revolve steam after desolventizing 1,2; 4-triphenyl-5-ester group imidazoles 85mg, yield 77%.
Embodiment 7 is with phenyl thiazolinyl nitrine 65mg (0.30mmol), phenyl nitrone 177mg (0.90mmol), anhydrous magnesium sulfate 150mg (1.24mmol) and 1, and 2-ethylene dichloride 5mL places the 50mL there-necked flask; Stirring heating, at 50 ℃ of reaction 24h, TLC detects and disappears until phenyl thiazolinyl nitrine; After question response finishes, cooling concentration, with enriched material with hexanaphthene: ETHYLE ACETATE (V/V) is that 10: 1 mixed solvent is as the column chromatography wash-out of eluent; The elutriant part of all products that collection monitors, revolve steam after desolventizing 1,2; 4-triphenyl-5-ester group imidazoles 25mg, yield 23%.Embodiment 8 is with phenyl thiazolinyl nitrine 65mg (0.30mmol), phenyl nitrone 177mg (0.90mmol), anhydrous magnesium sulfate 150mg (1.24mmol) and 1, and 2-ethylene dichloride 5mL places the 50mL there-necked flask; Stirring heating, at 80 ℃ of reaction 24h, TLC detects and disappears until phenyl thiazolinyl nitrine; After question response finishes, cooling concentration, with enriched material with hexanaphthene: ETHYLE ACETATE (V/V) is that 10: 1 mixed solvent is as the column chromatography wash-out of eluent; The elutriant part of all products that collection monitors, revolve steam after desolventizing 1,2; 4-triphenyl-5-ester group imidazoles 24mg, yield 22%.
Claims (6)
1. the compound method of four substituted imidazole compounds shown in formula III, described method is to be that raw material is promotor and 1 at anhydrous magnesium sulfate suc as formula the thiazolinyl nitrine shown in the I, suc as formula the nitrone shown in the II, the 2-ethylene dichloride is that solvent exists down; Under 50～80 ℃ of conditions, react 24～48h, TLC detects until the thiazolinyl nitrine and disappears, after question response finishes; With the reaction solution cooling concentration, through with sherwood oil: the ETHYLE ACETATE volume ratio be 10: 1 mixed solvent as eluent column chromatography wash-out, collect the elutriant part of all products that monitor; Revolve and get 1 after steaming desolventizes; 2,4,5-four substituted imidazoles; Described thiazolinyl nitrine: nitrone: anhydrous magnesium sulfate amount of substance ratio is 1: 1.5～3: 2～8; Described thiazolinyl nitrine: 1,2-ethylene dichloride amount of substance ratio is 1: 210～300, in formula I, formula II or the formula III, R
1For-C
6H
5Or-3,4,5-tri-MeOC
6H
2R
2For-CO
2Et; R
3For-C
6H
5Or-p-MeOC
6H
4R
4For-C
6H
5Or-p-ClC
6H
4,
2. the compound method of four substituted imidazole compounds shown in formula III, described method is to be that raw material is promotor and 1 at anhydrous magnesium sulfate suc as formula the thiazolinyl nitrine shown in the I, suc as formula the nitrone shown in the II, the 2-ethylene dichloride is that solvent exists down; Under 66 ℃ of conditions, react 48h, TLC detects until the thiazolinyl nitrine and disappears, after question response finishes; With the reaction solution cooling concentration, through with sherwood oil: the ETHYLE ACETATE volume ratio is that 10: 1 mixed solvent is as the column chromatography wash-out of eluent wash-out, the elutriant part of collecting all products that monitor; Revolve and get 1 after steaming desolventizes; 2,4,5-four substituted imidazoles; Described thiazolinyl nitrine: nitrone: anhydrous magnesium sulfate amount of substance ratio is 1: 3: 4; Described thiazolinyl nitrine: 1,2-ethylene dichloride amount of substance ratio is 1: 210, in formula I, formula II or the formula III, R
1For-C
6H
5Or-3,4,5-tri-MeOC
6H
2R
2For-CO
2Et; R
3For-C
6H
5Or-p-MeOC
6H
4R
4For-C
6H
5Or-p-ClC
6H
4
3. the compound method of four substituted imidazole compounds as claimed in claim 1 is characterized in that described temperature of reaction is 66 ℃.
4. the compound method of four substituted imidazole compounds as claimed in claim 1 is characterized in that the described reaction times is 48h.
5. the compound method of four substituted imidazole compounds as claimed in claim 1 is characterized in that described thiazolinyl nitrine: nitrone: anhydrous magnesium sulfate amount of substance ratio is 1: 3: 4.
6. the compound method of four substituted imidazole compounds as claimed in claim 1 is characterized in that described thiazolinyl nitrine: 1, and 2-ethylene dichloride amount of substance ratio is 1: 210.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104529809A (en) * | 2014-10-10 | 2015-04-22 | 浙江大学 | Preparation method polysubstituted imidazole derivatives |
| CN106866541A (en) * | 2015-12-11 | 2017-06-20 | 中国科学院大连化学物理研究所 | A kind of method for preparing benzimidazoles derivative |
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2011
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| CN1138326A (en) * | 1993-12-21 | 1996-12-18 | 拜尔公司 | N-substituted aryl trifluoromethyl imidazoles |
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| NIKNAM K. ET AL: "Synthesis of 1,2,4,5-tetrasubstituted imidazoles using silica-bonded propylpiperazine N -sulfamic acid as a recyclable solid acid catalyst", 《TETRAHEDRON LETTERS》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104529809A (en) * | 2014-10-10 | 2015-04-22 | 浙江大学 | Preparation method polysubstituted imidazole derivatives |
| CN106866541A (en) * | 2015-12-11 | 2017-06-20 | 中国科学院大连化学物理研究所 | A kind of method for preparing benzimidazoles derivative |
| CN106866541B (en) * | 2015-12-11 | 2019-03-01 | 中国科学院大连化学物理研究所 | A method of preparing benzimidazoles derivative |
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