CN111100071A - Method for synthesizing 2-cyano-5-aryl-1H-imidazole compound - Google Patents
Method for synthesizing 2-cyano-5-aryl-1H-imidazole compound Download PDFInfo
- Publication number
- CN111100071A CN111100071A CN201911315336.6A CN201911315336A CN111100071A CN 111100071 A CN111100071 A CN 111100071A CN 201911315336 A CN201911315336 A CN 201911315336A CN 111100071 A CN111100071 A CN 111100071A
- Authority
- CN
- China
- Prior art keywords
- aryl
- arylethanone
- dihalogen
- compound
- cyano
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings 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
- C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Abstract
The invention discloses a method for synthesizing 2-cyano-5-aryl-1H-imidazole compounds, which comprises the steps of taking α -dihalogen arylethanone and 2, 2-dialkoxy acetaldehyde as raw materials, performing cyclization with a nitrogen source under the action of an acid-binding agent to synthesize 2- (dialkoxymethyl) -5-aryl-1H-imidazole compounds, and then performing oximation, dehydration and other reactions to prepare the 2-cyano-5-aryl-1H-imidazole compounds.
Description
Technical Field
The invention belongs to the field of synthesis of pesticide raw materials and intermediates, and particularly relates to a method for synthesizing 2-cyano-5-aryl-1H-imidazole compounds.
Background
The 2-site dialkoxymethyl of the 2- (dialkoxymethyl) -5-aryl-1H-imidazole compound can form a naked aldehyde group after being acidified to remove acetal protection, the aldehyde group has high reactivity, and can be converted by simple functional groups to generate derivatives such as carboxyl, primary alcohol, amide, imine, cyano and the like, and similar derivatives can be used as intermediates to synthesize various molecules with biological activity, for example, 2-cyano-5-p-tolyl-1H-imidazole is an important intermediate for synthesizing 4-chloro-2-cyano-N, N-dimethyl-5-p-tolylimidazole-1-sulfonamide, 4-chloro-2-cyano-N, N-dimethyl-5-p-tolylimidazole-1-sulfonamide is a novel bactericide developed by Nippon stone original product company, has the advantages of strong pertinence, high efficiency, no cross resistance, long lasting period, safety, environmental protection and the like, has excellent performance, can be widely used for sterilizing melons and vegetables, is also suitable for lawn, egg mycosis represented by downy mildew, rape and plasmodioma disease, the invention discloses a special-based aryl-2-aryl-halogen oxime-1H-1-aryl-2-aryl-halogen compound prepared by a one-2-halogen cyclization reaction method, and a cyclization reaction of aryl-5-cyano-5-cyano-imidazole-cyano-5-imidazole-oxime compound.
At present, the literature discloses methods for preparing 2-cyano-5-aryl-1H-imidazoles, which mainly comprise the following three methods: 1) a method for introducing a cyano group at the 2-position of an imidazole ring by using n-butyllithium as described in patent BR8801098A 1. The raw material n-butyllithium used by the method is expensive, the reaction needs low temperature of-70 ℃, the reaction conditions are harsh, and the water pollution is caused by more waste water in the butyl lithium treatment process; 2) the introduction of a cyano group at position 2 of the imidazole ring by means of the formation of an imide structure is described in patent EP0365030A 1. The raw material 1-methoxy-1-imino-2, 2-diethoxyethane used by the method is difficult to prepare, easy to deteriorate and expensive; 3) the method of patent EP0705823A1 adopts glyoxal to close rings, and then utilizes aldoximyl to introduce cyano group into 2-position of imidazole ring, the synthesis of intermediate 4(5) -chloro-2-cyano-5 (4) - (4' -methylphenyl) imidazole adopts sulfur monochloride as chlorinating agent and reducing agent, the particle size of sulfur generated by reaction is very fine, the treatment process is complex, N-dimethylformamide is used as solvent in the reaction, and the solvent can not be recovered. The above method has the disadvantages of expensive raw materials, harsh operating conditions or unrecoverable solvent.
Disclosure of Invention
The invention aims to solve the technical problem of providing a method for synthesizing 2-cyano-5-aryl-1H-imidazole compounds, which has cheap and easily obtained raw materials, simple process and mild reaction conditions.
The invention discloses a method for synthesizing 2-cyano-5-aryl-1H-imidazole compounds, the reaction chemical equation of the method is shown as formula (I),
wherein Ar is an aryl group such as phenyl, substituted phenyl, furyl, thiazolyl, naphthyl, and the like; x is one or two of I, Br and Cl; r is one of chain alkyl such as methyl, ethyl, isopropyl, etc. (CH)2)2、(CH2)3An isocyclic alkyl group; the acid-binding agent is one or more of sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, triethylamine, pyridine, 4-N, N-dimethylpyridine, N-methylmorpholine, dimethylamine, diethylamine, pyrrole, morpholine, 2-methylpyrrole, etc.; the nitrogen source is one or more of ammonia gas, strong ammonia water, ammonium carbonate, ammonium oxalate, ammonium acetate and the like;
the experimental procedure was as follows:
(1) sequentially adding α -dihalogen arylethanone, a solvent, 2-dialkoxy acetaldehyde, an acid-binding agent and a liquid or solid nitrogen source into a three-neck round-bottom flask with a thermometer, a reflux condenser and a stirring device (if gaseous nitrogen source ammonia is used, the ammonia is heated and then introduced), wherein the solvent is one or more of N, N-dimethylformamide, dimethyl sulfoxide, water, methanol, ethanol, N-propanol, N-butanol, isopropanol, tert-butanol, toluene and xylene, the mass ratio of the solvent to α -dihalogen arylethanone is 3-10: 1, the molar ratio of α -dihalogen arylethanone to 2, 2-dialkoxy acetaldehyde is 1: 1-3, the molar ratio of α -dihalogen arylethanone to acid-binding agent is 1: 2-5, and the molar ratio of α -dihalogen arylethanone to nitrogen source is 1: 2-16;
(2) heating to 30-100 ℃ under stirring, starting to introduce ammonia gas if the nitrogen source is gaseous ammonia gas, monitoring the reaction by a liquid phase, and finishing the reaction when the content of the raw material α -dihalogen arylethanone is less than 2% (about 10 h);
(3) cooling to 40 ℃, adding water, stirring for 1h, generating a large amount of solid, and filtering to obtain a crude product, wherein the mass ratio of the added water to the α -dihalogen arylethanone is 3-10: 1;
(4) pulping the solid filter with hot water (40 ℃) for 1 hour, filtering to obtain a product 2- (dialkoxymethyl) -5-aryl-1H-imidazole (i), and drying for later use;
(5) adding the compound (i) into a mixed solution of 10% dilute sulfuric acid and methanol, stirring at 35 ℃ for two hours, neutralizing with 10% sodium hydroxide until the pH value is 7, evaporating the methanol to dryness to obtain a solid suspension, filtering to obtain 2-aldehyde-5-aryl-1H-imidazole (ii), and drying for later use; wherein the mass ratio of 10% dilute sulfuric acid to methanol is 1: 3; the mass ratio of the mixed solution of dilute sulfuric acid and methanol to the compound (i) is 3: 1;
(6) mixing 2-aldehyde-5-aryl-1H-imidazole and hydroxylamine sulfate in methanol, refluxing for 2 hours, evaporating the methanol to dryness to obtain a compound (iii), and drying for later use; wherein the molar ratio of the 2-aldehyde-5-aryl-1H-imidazole to the hydroxylamine sulfate is 1:1.1, and the mass ratio of the 2-aldehyde-5-aryl-1H-imidazole to the solvent methanol is 1: 3;
(7) suspending the compound (iii) in toluene, heating to 50 ℃, dropwise adding thionyl chloride while stirring, dropwise adding the compound for 30 minutes, then keeping the temperature for reaction for 3 hours, cooling to room temperature, dropwise adding 10% sodium hydroxide while stirring for neutralization until the pH value is 7, layering, separating a toluene layer, drying with anhydrous sodium sulfate, and evaporating the toluene to dryness to obtain a solid 2-cyano-5-aryl-1H-imidazole compound; wherein the mass ratio of the compound (iii) to toluene is 1: 3; the molar ratio of compound (iii) to thionyl chloride was 1: 1.05.
The acid-binding agent with optimized closed-loop is one or more of organic bases such as triethylamine, pyridine, 4-N, N-dimethylpyridine, N-methylmorpholine, dimethylamine, diethylamine, pyrrole, morpholine and 2-methylpyrrole, and the molar ratio of α -dihalogen arylethanone to the acid-binding agent is 1: 2-3.
The optimized reaction temperature of the ring closing reaction is 30-80 ℃.
The optimized reaction solvent of the cyclization reaction is dimethyl sulfoxide, water, methanol, ethanol and toluene, and the mass ratio of the solvent amount to α -dihalogen arylethanone is 3-5: 1.
The optimized mole ratio of α -dihalogen arylethanone to nitrogen source ammonium carbonate and ammonium oxalate in the cyclization reaction is 1: 2-3, the mole ratio of α -dihalogen arylethanone to nitrogen source ammonium acetate is 1: 4-6, and the mole ratio of α -dihalogen arylethanone to nitrogen source ammonia and concentrated ammonia is 1: 10-16.
The invention has the advantages that:
the method is characterized in that α -dihalogen arylethanone which is cheap and easy to obtain reacts with 2, 2-dimethoxy acetaldehyde to prepare the 2- (dialkoxymethyl) -5-aryl-1H-imidazole compound, and the 2- (dialkoxymethyl) -5-aryl-1H-imidazole compound is subjected to oximation, dehydration and other steps to prepare the 2-cyano-5-aryl-1H-imidazole compound, wherein the reaction conditions are mild, the reaction temperature is less than or equal to 80 ℃, the reaction can be carried out by heating in a water bath, the operation is simple, the intermediate does not need to be purified, the yield is high, and the total yield of the four-step reaction is more than or equal to 82%.
Detailed Description
The present invention will be further described with reference to the following examples, which are intended to better understand the essential features of the present invention, and therefore should not be construed as limiting the scope of the present invention.
Example 1
Adding α -dibromoacetophenone 27.8g, methanol 139g, 2-dimethoxyacetaldehyde 60% aqueous solution 34.7g, triethylamine 30.4g and ammonium acetate 29.6g into a three-neck round-bottom flask with a thermometer, a reflux condenser and a stirring device, heating to 40 ℃ while stirring, stirring for reaction, monitoring the reaction by TLC, stopping the reaction (about 10H) when the raw material α -dibromoacetophenone disappears, adding water 139g at 40 ℃ and stirring for 1H to generate a large amount of solid, filtering to obtain a crude product, pulping the filtered solid with warm water 50g at 40 ℃ for stirring for 1H, filtering, and drying to obtain the product 2- (dimethoxymethyl) -5-phenyl-1H-imidazole 19.2g with the yield of 91% and the content of 96.3%.
Example 2
α -dichlorophenyl acetophenone 18.9g, methanol 139g, 2-dimethoxy acetaldehyde 60% water solution 34.7g, triethylamine 30.4g and ammonium acetate 29.6g are added into a three-mouth round bottom flask with a thermometer, a reflux condenser tube and a stirring device in sequence, the temperature is raised to 40 ℃ with stirring, the reaction is stirred, the TLC monitors the reaction, the reaction is finished (about 16H) when the raw material α -dichlorophenyl acetophenone disappears, water 139g is added into the reaction at 40 ℃ and stirred for 1H, a large amount of solid is generated, a crude product is obtained by filtration, the filtered solid is beaten and stirred for 1H with warm water 50g at 40 ℃, the temperature is filtered, and the product 2- (dimethoxymethyl) -5-phenyl-1H-imidazole 18.4g is obtained by filtration and drying, the yield is 84.3%, and the content is.
Example 3
α -dibromoacetophenone 27.8g, methanol 139g, 2-dimethoxyacetaldehyde 60% water solution 34.7g, triethylamine 30.4g and ammonium carbonate 19.2g are sequentially added into a three-mouth round-bottom flask with a thermometer, a reflux condenser tube and a stirring device, the temperature is raised to 40 ℃ while stirring, the reaction is stirred, TLC monitors the reaction, the reaction is finished (about 10H) when the raw material α -dibromoacetophenone disappears, water 139g is added at 40 ℃ and stirred for 1H, a large amount of solid is generated, a crude product is obtained by filtration, the filtered solid is beaten with warm water 50g at 40 ℃ and stirred for 1H, and the product 2- (dimethoxymethyl) -5-phenyl-1H-imidazole 19.7g is obtained by filtration and drying, the yield is 90.2%, and the content is 96.1%.
Example 4
The procedure was substantially the same as in example 1, except that the amount of ammonium acetate as the nitrogen source used was 44.4g, to give 18.3g of 2- (dimethoxymethyl) -5-phenyl-1H-imidazole in a yield of 84.0% and a content of 95.7%.
Example 5
The procedure was substantially the same as in example 1, except that the reaction temperature was 80 ℃ to obtain 17.9g of 2- (dimethoxymethyl) -5-phenyl-1H-imidazole in a yield of 82.2% and a content of 93.9%.
Example 6
The procedure was essentially the same as in example 1, except that 139g of dimethyl sulfoxide was used as the solvent, and 14.36g of 2- (dimethoxymethyl) -5-phenyl-1H-imidazole was obtained in a yield of 65.8% and a content of 97.6%.
Example 7
The procedure was essentially the same as in example 1, except that 139g of water was used as the solvent, to give 16.85g of 2- (dimethoxymethyl) -5-phenyl-1H-imidazole in 77.2% yield and 94.5% content.
Example 8
The procedure was as in example 1 except that the acid-binding agent used was sodium carbonate 21.2g to give 2- (dimethoxymethyl) -5-phenyl-1H-imidazole 9.1g in 41.8% yield with a content of 91.2%.
Example 9
α -dibromoacetophenone 27.8g, water 139g, 2-dimethoxyacetaldehyde 60% aqueous solution 34.7g and triethylamine 30.4g are sequentially added into a three-neck round-bottom flask with a thermometer, a reflux condenser tube and a stirring device, ammonia gas is introduced when the temperature is raised to 50 ℃ under stirring, the reaction is stirred, the TLC monitors the reaction, the reaction is finished when the raw material α -dibromoacetophenone disappears (about 8H), the amount of the introduced ammonia gas is 17.5g, the temperature is lowered to 40 ℃, water 139g is added, the mixture is stirred for 1H, a large amount of solid is generated, a crude product is obtained by filtration, the above filtration solid is beaten and stirred for 1H with warm water 50g at 40 ℃, the filtration solid is filtered, and the product 2- (dimethoxymethyl) -5-phenyl-1H-imidazole 17.5g is obtained by drying, the yield is 80.1%, and the.
Example 10
α -dichloro (4-methyl) acetophenone 20.3g, water 139g, 2-dimethoxyacetaldehyde 60% water solution 34.7g and triethylamine 30.4g are sequentially added into a three-mouth round-bottom flask with a thermometer, a reflux condenser and a stirring device, ammonia gas is introduced when the temperature is raised to 50 ℃ under stirring, the reaction is monitored by TLC, the reaction is finished when the raw material α -dichloro (4-methyl) acetophenone disappears (about 10 hours), the amount of the introduced ammonia gas is 18g, the temperature is reduced to 40 ℃, water 139g is added and stirred for 1 hour, a large amount of solid is generated and filtered to obtain a crude product, the filtered solid is beaten and stirred for 1 hour by warm water 50g at the temperature of 40 ℃, the filtered solid is filtered and dried to obtain the product 2- (dimethoxymethyl) -5- (4' -methyl) phenyl-1H-imidazole 18.86g, the yield is 81.3%, and the content is 96.4%.
Example 11
Mixing 30 g of 10% dilute sulfuric acid and 90 g of methanol, and uniformly stirring for later use; stirring and mixing 21.8g of 2- (dimethoxymethyl) -5-phenyl-1H-imidazole with 65.4 g of mixed solution of dilute sulfuric acid and methanol, stirring for two hours at 35 ℃, neutralizing with 10% sodium hydroxide until the pH value is 7, evaporating the methanol to dryness to obtain solid suspended matters, filtering and drying to obtain 16.7 g of 2-aldehyde-5-phenyl-1H-imidazole, wherein the yield is 97%, and the content is 96%;
adding 16.7 g of 2-aldehyde-5-phenyl-1H-imidazole and 8.75 g of hydroxylamine sulfate into 50g of methanol, refluxing for 2 hours, cooling to room temperature, dropwise adding a 10% sodium hydroxide solution for neutralization until the pH value is 7, evaporating the methanol to dryness to obtain a solid product, drying, weighing 17.8 g, obtaining a yield of 98%, and obtaining a content of 96.9%;
suspending 17.8 g of the compound in 53.4 g of dry toluene, heating to 50 ℃, dropwise adding 11.9 g of thionyl chloride while stirring, dropwise adding the thionyl chloride after 30 minutes, carrying out heat preservation reaction for 3 hours, cooling to room temperature, dropwise adding 10% sodium hydroxide while stirring to neutralize until the pH value is 7, layering, separating a toluene layer, drying by anhydrous sodium sulfate, evaporating the toluene to dryness to obtain a solid, drying by a vacuum oven to obtain 15.3 g of dry 2-cyano-5-phenyl-1H-imidazole, wherein the yield is 95%, and the content is 96.5%.
Claims (7)
1. A method for synthesizing 2-cyano-5-aryl-1H-imidazole compounds is characterized in that the reaction chemical equation is shown as the formula (I),
firstly α -dihalogen arylethanone and 2, 2-dialkoxy acetaldehyde undergo a cyclization reaction in a nitrogen source environment to prepare a 2- (dialkoxymethyl) -5-aryl-1H-imidazole compound, and then undergo acidification, oximation and dehydration reactions to prepare the 2-cyano-5-aryl-1H-imidazole compound, wherein
Ar is phenyl, substituted phenyl, furyl, thiazolyl or naphthyl;
x is one or two of I, Br and Cl;
r is one of methyl, ethyl and isopropyl or (CH)2)2、(CH2)3A cyclic alkyl group of (a);
the acid-binding agent is one or more of sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, triethylamine, pyridine, 4-N, N-dimethylpyridine, N-methylmorpholine, dimethylamine, diethylamine, pyrrole, morpholine and 2-methylpyrrole;
the nitrogen source is one or more of ammonia gas, strong ammonia water, ammonium carbonate, ammonium oxalate and ammonium acetate.
2. The method for synthesizing 2-cyano-5-aryl-1H-imidazoles as claimed in claim 1, comprising the steps of:
(1) adding α -dihalogen arylethanone, a solvent, 2-dialkoxy acetaldehyde, an acid-binding agent and a liquid or solid nitrogen source into a three-neck round-bottom flask with a thermometer, a reflux condenser and a stirring device in sequence, heating and then introducing ammonia gas if the nitrogen source is gaseous ammonia gas, wherein the solvent is one or more of N, N-dimethylformamide, dimethyl sulfoxide, water, methanol, ethanol, N-propanol, N-butanol, isopropanol, tert-butanol, toluene and xylene, the mass ratio of the solvent to α -dihalogen arylethanone is 3-10: 1, the molar ratio of α -dihalogen arylethanone to 2, 2-dialkoxy acetaldehyde is 1: 1-3, the molar ratio of α -dihalogen arylethanone to the acid-binding agent is 1: 2-5, and the molar ratio of α -dihalogen arylethanone to the nitrogen source is 1: 2-16;
(2) heating to 30-100 ℃ under stirring, introducing ammonia gas if the nitrogen source is gaseous ammonia gas, monitoring the reaction by a liquid phase, and finishing the reaction for 10 hours when the content of the raw material α -dihalogen arylethanone is less than 2%;
(3) cooling to 40 ℃, adding water, stirring for 1h, generating a large amount of solid, and filtering to obtain a crude product, wherein the mass ratio of the added water to the α -dihalogen arylethanone is 3-10: 1;
(4) pulping the filtered solid with hot water, stirring for 1h, filtering, and drying for later use to obtain a compound i;
(5) adding the compound i into a mixed solution of 10 wt% of dilute sulfuric acid and methanol, stirring for two hours at 35 ℃, neutralizing with 10 wt% of sodium hydroxide until the pH value is 7, evaporating the methanol to dryness to obtain solid suspended matters, filtering to obtain 2-aldehyde-5-aryl-1H-imidazole and a compound ii, and drying for later use; wherein the mass ratio of 10 wt% dilute sulfuric acid to methanol is 1: 3; the mass ratio of the mixed solution of 10 wt% dilute sulfuric acid and methanol to the compound i is 3: 1;
(6) mixing the compound ii with hydroxylamine sulfate, adding the mixture into a methanol solution, refluxing for 2 hours, evaporating the methanol to obtain a compound iii, and drying for later use; wherein the molar ratio of the compound ii to the hydroxylamine sulfate is 1:1.1, and the mass ratio of the compound ii to the solvent methanol is 1: 3;
(7) suspending the compound iii in toluene, heating to 50 ℃, dropwise adding thionyl chloride while stirring, dropwise adding the compound iii after 30 minutes, then keeping the temperature for reaction for 3 hours, cooling to room temperature, dropwise adding 10% sodium hydroxide while stirring for neutralization until the pH value is 7, layering, separating a toluene layer, drying anhydrous sodium sulfate, and evaporating the toluene to dryness to obtain a solid 2-cyano-5-aryl-1H-imidazole compound;
wherein the mass ratio of the compound iii to the toluene is 1: 3; the molar ratio of the compound iii to the thionyl chloride is 1: 1.05.
3. The method for synthesizing 2-cyano-5-aryl-1H-imidazole according to claim 2, wherein the molar ratio of α -dihalogen arylethanone to acid-binding agent is 1: 2-3.
4. The method for synthesizing the 2-cyano-5-aryl-1H-imidazole compounds according to claim 2, wherein the optimal reaction temperature of the cyclization reaction is 50-80 ℃.
5. The method for synthesizing the 2-cyano-5-aryl-1H-imidazole compound according to claim 2, wherein the mass ratio of the solvent dosage to the α -dihalogen arylethanone is 3-5: 1.
6. The method for synthesizing the 2-cyano-5-aryl-1H-imidazole compounds according to claim 2, wherein the molar ratio of the α -dihalogenated arylethanone to the 2, 2-dialkoxyacetaldehyde is 1: 1-2.
7. The method for synthesizing the 2-cyano-5-aryl-1H-imidazole compounds according to claim 2, wherein the molar ratio of the α -dihalogen arylethanone to the nitrogen source ammonium carbonate or ammonium oxalate is 1: 2-3, the molar ratio of the α -dihalogen arylethanone to the nitrogen source ammonium acetate is 1: 4-6, and the molar ratio of the α -dihalogen arylethanone to the nitrogen source ammonia gas or concentrated ammonia water is 1: 10-16.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911315336.6A CN111100071A (en) | 2019-12-19 | 2019-12-19 | Method for synthesizing 2-cyano-5-aryl-1H-imidazole compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911315336.6A CN111100071A (en) | 2019-12-19 | 2019-12-19 | Method for synthesizing 2-cyano-5-aryl-1H-imidazole compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN111100071A true CN111100071A (en) | 2020-05-05 |
Family
ID=70422574
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201911315336.6A Pending CN111100071A (en) | 2019-12-19 | 2019-12-19 | Method for synthesizing 2-cyano-5-aryl-1H-imidazole compound |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN111100071A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115385860A (en) * | 2022-07-20 | 2022-11-25 | 西安近代化学研究所 | Method for synthesizing 2-cyano-5-aryl-1H-imidazole compound |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07215946A (en) * | 1994-02-04 | 1995-08-15 | Ishihara Sangyo Kaisha Ltd | Production of 2-cyanoimidazole compound |
| CN1684957A (en) * | 2002-08-02 | 2005-10-19 | 阿根塔发明有限公司 | Substituted thienyl-hydroxamic acids as histone deacetylase inhibitors |
| CN102124002A (en) * | 2008-06-20 | 2011-07-13 | H.隆德贝克有限公司 | Novel phenylimidazole derivatives as pde10a enzyme inhibitors |
| CN105683176A (en) * | 2013-09-04 | 2016-06-15 | 亚历克撒治疗公司 | Liver x receptor (LXR) modulators |
-
2019
- 2019-12-19 CN CN201911315336.6A patent/CN111100071A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07215946A (en) * | 1994-02-04 | 1995-08-15 | Ishihara Sangyo Kaisha Ltd | Production of 2-cyanoimidazole compound |
| CN1684957A (en) * | 2002-08-02 | 2005-10-19 | 阿根塔发明有限公司 | Substituted thienyl-hydroxamic acids as histone deacetylase inhibitors |
| CN102124002A (en) * | 2008-06-20 | 2011-07-13 | H.隆德贝克有限公司 | Novel phenylimidazole derivatives as pde10a enzyme inhibitors |
| CN105683176A (en) * | 2013-09-04 | 2016-06-15 | 亚历克撒治疗公司 | Liver x receptor (LXR) modulators |
Non-Patent Citations (1)
| Title |
|---|
| 本书编写组: "《有机化学精析精练》", 31 March 2004, pages: 151 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115385860A (en) * | 2022-07-20 | 2022-11-25 | 西安近代化学研究所 | Method for synthesizing 2-cyano-5-aryl-1H-imidazole compound |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SU884570A3 (en) | Method of preparing carbonyl-substituted 1-sulfonylbenzimidazoles | |
| JP4136866B2 (en) | Novel industrial synthesis method of tetraesters of 5- [bis (carboxymethyl) amino] -3-carboxymethyl-4-cyano-2-thiophenecarboxylic acid, and divalent salts of ranelic acid and their hydrates Application to synthesis | |
| IL167314A (en) | Method for the industrial synthesis of the methoyl diester of 5-amino-3-carboxymethyl-4-cyano-2-thiophenecarboxylic acid and application of divalent salts of ranelic acid and the hydrates thereof in said synthesis | |
| JP6811717B2 (en) | Methods for the preparation of topiroxostat and its intermediates | |
| CN110981813A (en) | Synthetic method of 2-cyano-5-aryl-1H-imidazole compound | |
| CN111100071A (en) | Method for synthesizing 2-cyano-5-aryl-1H-imidazole compound | |
| CN113788766A (en) | Preparation method of atorvastatin calcium intermediate | |
| CA1191139A (en) | Aroyl amino acids | |
| Zhang et al. | Dimethylammonium Chlorochromate Adsorbed on Alumina: 1 A Mild, Convenient and Inexpensive Reagent for Cleavage of Carbon-Nitrogen Double Bonds Under Non-Aqueous Condition | |
| CN109896989B (en) | Synthesis method of 5-oxo-2H-aromatic ring [ g ] indole-1-oxide | |
| CN116606259B (en) | Preparation method of Sha Mizhu key intermediate of anti-insect veterinary drug | |
| CN106866544B (en) | 2- (2-hydroxyphenyl) -1H-benzimidazole and derivative, synthetic method and application thereof | |
| CN111592486B (en) | Method for constructing 3,5-disubstituted pyridine by cyclization reaction of aryl ethylene and N, N-dimethylformamide | |
| CN113943281B (en) | Synthetic method and application of isoxazole pyrimidine derivative | |
| CN113896722B (en) | Benzamide compound containing thiadiazole group and preparation method and application thereof | |
| Ceulemans et al. | Neighbouring group effects on rates of thermolysis of 4-azidothiazoles | |
| JPH01316352A (en) | Production of 3-cyano-4-arylpyrrole | |
| RU2428418C1 (en) | Method of producing n-nitromethyl azoles | |
| Mukaiyama et al. | The Reactions of β-Ketosulfonium Salts with Sulfenamide Derivatives | |
| KR100856133B1 (en) | Improved process for preparing atorvastatin | |
| SU1685938A1 (en) | Method for obtaining 2-alkyl(aryl)thiophenes | |
| EP3609877B1 (en) | Process for the synthesis of firocoxib | |
| CN116082214A (en) | 2-aryl-3-tert-butylindole compound, preparation method and application thereof | |
| SU503517A3 (en) | The method of obtaining derivatives of indole acetic acid or their salts | |
| CN116102391A (en) | Disulfide transfer reagent and synthesis and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |