CN110283096A - A kind of ɑ-amino amide class compound and preparation method thereof of Cu-MOF catalysis - Google Patents
A kind of ɑ-amino amide class compound and preparation method thereof of Cu-MOF catalysis Download PDFInfo
- Publication number
- CN110283096A CN110283096A CN201910595983.0A CN201910595983A CN110283096A CN 110283096 A CN110283096 A CN 110283096A CN 201910595983 A CN201910595983 A CN 201910595983A CN 110283096 A CN110283096 A CN 110283096A
- Authority
- CN
- China
- Prior art keywords
- mof
- catalyst
- isonitrile
- reaction
- class compound
- 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
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B43/00—Formation or introduction of functional groups containing nitrogen
- C07B43/06—Formation or introduction of functional groups containing nitrogen of amide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
- C07C237/06—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
- C07C237/12—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/20—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C247/00—Compounds containing azido groups
- C07C247/16—Compounds containing azido groups with azido groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C247/18—Compounds containing azido groups with azido groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
Abstract
The present invention relates to a kind of preparation of amides compound, chemical structural formulas are as follows:Wherein, substituent R1For any one in benzyl, alkyl, propyl, isopropyl, aryl, substituted aryl, substituting group position and conjugate position are not fixed, R2For any one in aliphatic, aromatic series, substituted aryl and hetero-aromatic ring, substituting group position and conjugate position are not fixed, R3For tert-butyl, normal-butyl, cyclohexyl, ester group or phenyl sulfonyl.Preparation method is that three component Ugi reaction is occurred by aldehyde, amine and isonitrile and is obtained, reaction is simple, by-product is few, selectivity is preferable and yield is high by adding MOF-Cu catalyst at room temperature.The MOF-Cu catalyst is a kind of O-phthalic acids catalyst of organic metal framework material load being made of bivalent cupric ion and terphenyl tetrabasic carboxylic acid.There is no variations for rear structure before the reaction for the catalyst.MOF-Cu catalyst described in the step is through a series of post-processings, and repeatable circulation is catalyzed and catalytic effect remains unchanged.
Description
Technical field
The present invention relates to the three component UGI reactions and the preparation of ɑ-amino amide class compound of a kind of Cu-MOF catalysis, belong to
In technical field of organic synthesis.
Background technique
The Ugi reaction usually multi-component reaction as made of the condensation of aldehyde, amine, isonitrile and carboxylic acid, because of its mild condition, by-product
Less and the excellent characteristics such as yield height and be widely used in medicine and biological field.Scientists are also always all over the world simultaneously
Making great efforts to probe into highly efficient, economic, the environmentally friendly method based on Ugi reaction；And greatly tend to Ugi reaction and its
He, which reacts, is effectively combined, and pursues and is lived with least step number, minimum loss, highest Atom economy to synthesize to have
The molecule of property structure.It is put forward for the first time a kind of three component UGI reaction of Cu-MOF catalysis, and in this patent with this preparation method
Successfully synthesize a series of amide derivatives.
The invention patent introduces MOF-Cu catalyst, catalysis aldehyde compound and aminated compounds and different nitrile compounds
The Ugi-3CR of participation reacts, and one kettle way is efficiently prepared for a series of amide derivatives, after the reaction was completed, MOF-Cu catalyst
Through a series of post-processings, repeats circulation catalysis and catalytic effect influences less.
Summary of the invention
It is a primary object of the present invention to probe into and provide a kind of three component UGI reaction of Cu-MOF catalysis and ɑ-amido acyl
The preparation method of aminated compounds.
Technical scheme is as follows:
ɑ-amino amide class compound of a kind of Cu-MOF catalysis, the compound chemical structure formula are as follows:
(Ι) wherein, substituent R1For any one in benzyl, alkyl, propyl, isopropyl, aryl, substituted aryl, take
It is not fixed for base location and conjugate position, R2For any one in aliphatic, aromatic series, substituted aryl or hetero-aromatic ring, take
It is not fixed for base location and conjugate position, R3For tert-butyl, normal-butyl, cyclohexyl, ester group or phenyl sulfonyl.
Further preferably comprise the following structure ɑ-amino amide analog derivative of formula:
The synthesis method, the method includes following synthesis paths:
It the described method comprises the following steps:
(1) at room temperature, aldehyde compound is sequentially added into reactor, methanol solvate, aminated compounds is in room
The lower stirring of temperature dissolves it sufficiently；
(2) catalyst MOF-Cu and isonitrile are sequentially added after dissolving, after the reaction was continued 12h, reaction is detected through TLC and completes
Afterwards, MOF-Cu catalyst is filtered out, then removes solvent methanol under reduced pressure, residue is chromatographed by column, obtains target compound
I completes the preparation of amides compound.Next use is given over to after catalyst filtration.
The MOF-Cu catalyst is a kind of organic metal framework material being made of bivalent cupric ion and phthalic anhydride
The O-phthalic acids catalyst of load.There is no variations for rear structure before the reaction for the catalyst.
The preparation of MOF-Cu catalyst carrier MOF-Cu is referring to document: Xiang Lin, Junhua Jia, Xuebo
Zhao,K.Mark Thomas,Alexander J.Blake,Gavin S.Walker,Neil R.Champness,Peter
Hubberstey,and Martin Schroder,High H 2Adsorption by Coordination-Framework
Materials,Angew.Chem.Int.Ed.,2006,45:7358-7364.
The preparation of the MOF-Cu catalyst are as follows: the mixture that carrier MOF-Cu and phthalic anhydride mass ratio are 1:0.3
It is added in reaction kettle, the DMF: ethyl alcohol: the mixed solvent of water, reaction temperature that the volume ratio that solvent is 5 milliliters is 1:1:1 is
100 degrees Celsius.Reaction time is 24 hours.After the reaction was completed, it filters, solid, which dries, can be not only used for catalysis reaction.
The MOF-Cu catalyst is through a series of post-processings, and repeatable circulation is catalyzed and catalytic effect remains unchanged.
The aldehyde compound 1, aminated compounds 2, the molar ratio of isonitrile 3 are 1:0.5-2:0.5-2；Preferably
1:1:1.1。
The addition sequence of isonitrile 3 is to be eventually adding in the step, to aldehyde compound 1 and aminated compounds 2 in solvent
In be completely dissolved after.
The mole dosage of the catalyst MOF-Cu is 0.1-1 times of aldehyde compound.
The step reaction temperature is room temperature；Step (1) solvent is methanol or ethyl alcohol or water.
Amine described in the step is various aliphatic amines and aromatic amine, and aromatic amine includes aniline or substituted benzene
Amine.
Aldehyde described in the step is aliphatic aldehyde, aromatic aldehyde, and aromatic aldehyde includes benzaldehyde or substituted benzoyl
In aldehyde, substituting group position and conjugate position are not fixed.
Isonitrile described in the step include tert-butyl isonitrile, normal-butyl isonitrile, cyclohexyl isonitrile, ester group isonitrile and
Any one in phenyl sulfonyl isonitrile.
The present invention has the beneficial effect that:
1, present invention firstly discloses a kind of three component UGI being catalyzed with Cu-MOF reactions.The reaction method is easy to operate,
By-product is few, Atom economy and yield with higher；The MOF-Cu catalyst is post-treated, repeat circulation catalysis and it is right
Catalytic effect influences little.
2, the present invention is based on the three component UGI reactions of Cu-MOF catalysis to be prepared for a kind of ɑ-amino amide class compound, mentions
The novel preparation method that a kind of preparation cost is low, easy to operate and high reaction efficiency is supplied.
3, the present invention is prepared for a series of ɑ-amino amide analog derivative, such compound is as common and important nitrogenous
Heterocycle structure unit has wide potential using value in medicine and biosynthesis field, for example can be used to prepare dipeptides
Analog derivative and pyrazole derivatives.
Specific embodiment
The present invention is further illustrated below with reference to embodiment, but the scope of protection of present invention is not limited to implement
The range of example statement.
Instrument and reagent:
SHZ-E type circulating water type vacuum pump (the biochemical instrument plant of Shanghai Rong Ya)；DZE-6120 type vacuum oven (Shanghai
Heng Tian scientific instrument manufacturing company)；WRS-1A numeral melting point instrument (Shanghai Suoguang Optoelectronic Technology Co., Ltd.)；EB2005A electronics
Balance；ZF-I type ultraviolet analysis instrument for three purposed；DE-102J heat collecting type constant-temperature heating magnetic stirring apparatus (Gongyi City's grey hair chemical apparatuses
Factory)；DFX-5L/30 cryogenic thermostat reactive bath technique (hundred river instrument plant of Wuxi City)；(Linhai City is forever for 2YZ-4A type rotary vane type vacuum oil pump
Vast and boundless vacuum equipment factory).2- aldehyde benzoic acid methyl esters (AR), benzylamine (AR), cyclohexylamine (AR) and substituted aromatic amines etc., tert-butyl is different
Nitrile (AR), butyl isonitrile (AR), 2- Methyl isocyanoacetate (AR), cyclohexyl isocyanide etc. (AR), methanol (AR), ethyl acetate
(AR)。
Specific embodiment
The present invention is further illustrated below with reference to embodiment, but the scope of protection of present invention is not limited to implement
The range of example statement.
Instrument and reagent:
Fusing point is measured with X4 type melting point apparatus (production of Beijing third optical instrument factory), and thermometer is not calibrated；1H NMR and13600 type 600MHz core of C NMR 400 type 400MHz Nuclear Magnetic Resonance of Varian Mercury or Varian Mercury
Magnetic resonance device measurement, deuterated chloroform (CDCl3) solvent, TMS is internal standard；MS is measured using FinniganTrace mass spectrograph；Element
Analysis is measured using Vario EL III elemental analyser；Agents useful for same is that domestic (or import) chemistry is pure or analysis is pure.
Embodiment 1
A kind of side preparing 2- (2-azidophenyl)-N- (tert-butyl) -2- (phenylamino) acetamide
Method, including following experimental procedure:
At room temperature, sequentially add 2- nitrine benzaldehyde 1 (147mg, 1mmol) into reactor, methanol solvate and
Aniline 2 (93mg, 1.0mmol) stirs at room temperature dissolves it sufficiently, sequentially adds MOF-Cu catalyst (0.1%mol), uncle
Butyl isonitrile 3 (91mg, 1.1mmol), MeOH (5ml), it is to be dissolved after after the reaction was continued 12h, after the reaction was completed through TLC detection,
MOF-Cu catalyst is filtered out first, then removes solvent methanol under reduced pressure, and residue is chromatographed by column, obtains target chemical combination
Object 3a, yield 89%.
1H NMR(CDCl3, 400MHz) and δ (ppm) 7.42 (d, J=8.8Hz, 1H, Ar-H), 7.35 (t, J=8.8Hz, 1H,
), Ar-H 7.21 (d, J=6.8Hz, 1H, Ar-H), 7.16-7.08 (m, 3H, Ar-H), 6.72 (t, J=7.6Hz, 1H, Ar-H),
6.52 (d, J=8.8Hz, 2H, Ar-H), 6.48 (s, 1H, NH), 5.04 (d, J=2.8Hz, 1H, CH), 4.94 (s, 1H, NH),
1.31(s,9H,3CH3).
Embodiment 2
A method of preparing N- (tert-butyl) -2- (p-tolylamino) butanamide, including following experiment
Step:
At room temperature, propionic aldehyde 1 (58mg, 1mmol), methanol solvate and 4- methoxybenzene are sequentially added into reactor
Amine 2 (123mg, 1.0mmol) stirs at room temperature dissolves it sufficiently, sequentially adds MOF-Cu catalyst (0.1%mol), uncle
Butyl isonitrile 3 (91mg, 1.1mmol), MeOH (5ml), it is to be dissolved after after the reaction was continued 18h, after the reaction was completed through TLC detection,
MOF-Cu catalyst is filtered out first, then removes solvent methanol under reduced pressure, and residue is chromatographed by column, obtains target chemical combination
Object 3b, yield 91%.
1H NMR(CDCl3, 400MHz) and δ (ppm) 6.98 (d, J=8.0Hz, 2H, Ar-H), 6.63 (s, 1H, NH), 6.50
(t, J=8.4Hz, 2H, Ar-H), 3.72 (s, 1H, NH), 3.44-3.39 (m, 1H, CH), 2.23 (s, 3H, CH3),1.85-
1.58(m,2H,CH2),1.29(s,9H,3CH3), 1.00 (t, J=7.2Hz, 3H, CH3).
Embodiment 3
It is a kind of to prepare 2- (4-bromophenyl)-N- (tert-butyl) -2- ((4-methoxyphenyl) amino)
The method of acetamide, including following experimental procedure:
At room temperature, 4- bromobenzaldehyde 1 (184mg, 1mmol), methanol solvate and 4- are sequentially added into reactor
Aminoanisole 2 (123mg, 1.0mmol) stirs at room temperature dissolves it sufficiently, sequentially adds MOF-Cu catalyst (0.1%
Mol), tert-butyl isonitrile 3 (91mg, 1.1mmol), MeOH (5ml), it is to be dissolved after after the reaction was continued for 24 hours, detect and react through TLC
After the completion, MOF-Cu catalyst is filtered out first, then removes solvent methanol under reduced pressure, and residue is chromatographed by column, obtained
Target compound 3c, yield 89%.
1H NMR(CDCl3, 400MHz) and δ (ppm) 7.50 (d, J=8.4Hz, 2H, Ar-H), 7.29 (d, J=8.4Hz, 2H,
), Ar-H 7.78 (d, J=8.8Hz, 2H, Ar-H), 6.61 (s, 1H, NH), 6.57 (d, J=8.8Hz, 2H, Ar-H), 4.49 (s,
1H,CH),4.17(s,1H,NH),3.74(s,3H,OCH3),1.31(s,9H,3CH3).
Embodiment 4
According to the charged molar ratio and charging sequence and reaction condition of embodiment 1, reaction is expanded 10 times on an equal basis, is obtained
Target compound 3a, target yield 85%.
Embodiment 5
According to the charged molar ratio and charging sequence and reaction condition of embodiment 1, reaction is reduced 10 times on an equal basis, is obtained
Target compound 3a, target yield 92%.
Embodiment 6
According to the charged molar ratio and charging sequence and reaction condition of embodiment 1, post catalyst reaction filtering, after cleaning
It is catalyzed the reaction again, reaction effect remains unchanged, and can still arrive target compound 3a, target yield 89%.
Embodiment 7
According to the charged molar ratio and charging sequence and reaction condition of embodiment 1, post catalyst reaction filtering, after cleaning
It is catalyzed the reaction again.After being repeated 6 times, reaction effect variation less, can still arrive target compound 3a, target yield
It is 85%.
Embodiment 8
The compound can be used to synthesize dipeptides analog derivative.For example dipeptides analog derivative is prepared with glycine reactant.
Embodiment 9
The compound can be used to synthesize dipeptides analog derivative.For example pyrazole derivatives can be generated under heating condition.
Claims (10)
1. a kind of ɑ-amino amide class compound of Cu-MOF catalysis, which is characterized in that the reaction structure formula are as follows:
Wherein, substituent R1It is any in benzyl, alkyl, propyl, isopropyl, aryl, substituted aryl
One kind, substituting group position and conjugate position are not fixed；
R2For any one in aliphatic, aromatic series, substituted aryl or hetero-aromatic ring, substituting group position and conjugate position be not solid
It is fixed；
R3For tert-butyl, normal-butyl, cyclohexyl, ester group or phenyl sulfonyl.
2. ɑ-amino amide class compound of Cu-MOF catalysis according to claim 1, which is characterized in that the structural formula
Include:
3. ɑ-amino amide class compound method of Cu-MOF catalysis according to claim 1 or 2, which is characterized in that
It the described method comprises the following steps:
(1) at room temperature, aldehyde compound 1, solvent are sequentially added into reactor, aminated compounds 2 stirs at room temperature
Mixing dissolves it sufficiently；
(2) catalyst MOF-Cu and isonitrile 3 are sequentially added after dissolving, after the reaction was continued 12h, after the reaction was completed through TLC detection, filter
Then MOF-Cu catalyst out removes solvent under reduced pressure, residue is chromatographed by column, obtains target compound I, completes amide
The preparation of class compound gives over to next use after catalyst filtration；
The method includes following synthesis paths:
4. ɑ-amino amide class compound method of Cu-MOF catalysis according to claim 3, which is characterized in that described
Aldehyde compound 1, aminated compounds 2, the molar ratio of isonitrile 3 is 1:0.5-2:0.5-2, preferably 1:1:1.1；It is described
The mole dosage of catalyst MOF-Cu is 0.1-1 times of aldehyde compound 1.
5. ɑ-amino amide class compound method of Cu-MOF catalysis according to claim 3, which is characterized in that described
The addition sequence of isonitrile 3 is to be eventually adding in step, to aldehyde compound 1 and aminated compounds 2 in solvent methanol or ethyl alcohol or
After being completely dissolved in water.
6. ɑ-amino amide class compound method of Cu-MOF catalysis according to claim 3, it is characterised in that: described
Step reaction temperature is room temperature；Solvent described in the step (1), (2) is methanol or ethyl alcohol or water.
7. ɑ-amino amide class compound method of Cu-MOF catalysis according to claim 3, it is characterised in that: described
Amine described in step is various aliphatic amines and aromatic amine, and aromatic amine includes aniline or substituted aniline.
8. ɑ-amino amide class compound method of Cu-MOF catalysis according to claim 3, it is characterised in that: described
Aldehyde described in step is aliphatic aldehyde, aromatic aldehyde, and aromatic aldehyde includes benzaldehyde or substituted benzaldehyde, substituting group position
And conjugate position is not fixed.
9. ɑ-amino amide class compound method of Cu-MOF catalysis according to claim 3, it is characterised in that: described
Isonitrile described in step includes tert-butyl isonitrile, normal-butyl isonitrile, cyclohexyl isonitrile, ester group isonitrile or phenyl sulfonyl isonitrile
In any one.
10. ɑ-amino amide class compound of Cu-MOF catalysis according to claim 1 or 2 is preparing dipeptides analog derivative
And the application on pyrazole derivatives.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910595983.0A CN110283096A (en) | 2019-07-03 | 2019-07-03 | A kind of ɑ-amino amide class compound and preparation method thereof of Cu-MOF catalysis |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910595983.0A CN110283096A (en) | 2019-07-03 | 2019-07-03 | A kind of ɑ-amino amide class compound and preparation method thereof of Cu-MOF catalysis |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN110283096A true CN110283096A (en) | 2019-09-27 |
Family
ID=68020445
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201910595983.0A Pending CN110283096A (en) | 2019-07-03 | 2019-07-03 | A kind of ɑ-amino amide class compound and preparation method thereof of Cu-MOF catalysis |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN110283096A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111218006A (en) * | 2019-11-15 | 2020-06-02 | 三峡大学 | Nano-rod-shaped two-dimensional copper-based metal organic framework material, preparation method and application |
| CN113372276A (en) * | 2021-05-25 | 2021-09-10 | 三峡大学 | Indazole derivative and application thereof |
| CN114621149A (en) * | 2022-03-14 | 2022-06-14 | 三峡大学 | Method for synthesizing indazole compound by MOF-H248 catalysis |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20120107902A1 (en) * | 2010-10-27 | 2012-05-03 | Emory University | Processes For Forming Amide Bonds And Compositions Related Thereto |
| CN103097340A (en) * | 2010-07-16 | 2013-05-08 | 安吉奥斯医药品有限公司 | Therapeutically active compositions and their method of use |
| CN103920534A (en) * | 2014-03-04 | 2014-07-16 | 大连理工大学 | Catalyst of basic ionic liquid immobilized on metal-organic frameworks and preparation method thereof |
| CN103936536A (en) * | 2014-03-04 | 2014-07-23 | 大连理工大学 | Application of molecular size selective catalyst in Knoevenagel condensation reaction |
| CN109923112A (en) * | 2016-09-23 | 2019-06-21 | 先正达参股股份有限公司 | Kill the oxadiazole derivatives of microorganism |
-
2019
- 2019-07-03 CN CN201910595983.0A patent/CN110283096A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103097340A (en) * | 2010-07-16 | 2013-05-08 | 安吉奥斯医药品有限公司 | Therapeutically active compositions and their method of use |
| US20120107902A1 (en) * | 2010-10-27 | 2012-05-03 | Emory University | Processes For Forming Amide Bonds And Compositions Related Thereto |
| CN103920534A (en) * | 2014-03-04 | 2014-07-16 | 大连理工大学 | Catalyst of basic ionic liquid immobilized on metal-organic frameworks and preparation method thereof |
| CN103936536A (en) * | 2014-03-04 | 2014-07-23 | 大连理工大学 | Application of molecular size selective catalyst in Knoevenagel condensation reaction |
| CN109923112A (en) * | 2016-09-23 | 2019-06-21 | 先正达参股股份有限公司 | Kill the oxadiazole derivatives of microorganism |
Non-Patent Citations (4)
| Title |
|---|
| AGUIRRE-DIAZ等: "Synchronizing Substrate Activation Rates in Multicomponent Reactions with Metal-Organic Framework Catalysts", 《CHEMISTRY - A EUROPEAN JOURNAL 》 * |
| KUMAR, ATUL等: "Boric acid catalyzed Ugi three-component reaction in aqueous media", 《RSC ADVANCES》 * |
| REINARES-FISAC,等: "Anionic and neutral 2D indium metal-organic frameworks as catalysts for the Ugi one-pot multicomponent reaction", 《DALTON TRANSACTIONS》 * |
| YAO, LU 等: "Enantioselective [1,3] O-to-C rearrangement: dearomatization of alkyl 2-allyloxy/benzyloxy-1/3-naphthoates catalyzed by a chiral π-Cu(II) complex，Chemical Science", 《CHEMICAL SCIENCE》 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111218006A (en) * | 2019-11-15 | 2020-06-02 | 三峡大学 | Nano-rod-shaped two-dimensional copper-based metal organic framework material, preparation method and application |
| CN111218006B (en) * | 2019-11-15 | 2022-03-18 | 三峡大学 | Nano-rod-shaped two-dimensional copper-based metal organic framework material, preparation method and application |
| CN113372276A (en) * | 2021-05-25 | 2021-09-10 | 三峡大学 | Indazole derivative and application thereof |
| CN114621149A (en) * | 2022-03-14 | 2022-06-14 | 三峡大学 | Method for synthesizing indazole compound by MOF-H248 catalysis |
| CN114621149B (en) * | 2022-03-14 | 2023-11-21 | 三峡大学 | Method for synthesizing indazole compound by MOF-H248 catalysis |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN110283096A (en) | A kind of ɑ-amino amide class compound and preparation method thereof of Cu-MOF catalysis | |
| CN103880892B (en) | Acyl Ferrocene contracting S-methyldi-thiocarbazate Schiff and preparation method thereof | |
| CN101723771B (en) | Novel method for preparing beta-aminoketone, ester, nitrile and amide derivatives through catalysis of functional ionic liquid | |
| DK169074B1 (en) | Chiral rhodium-disphosphine complexes, process for their preparation and use of the complexes | |
| CN101362100A (en) | Chiral amine-(sulphur)urea double functional catalyst and synthesis method and use thereof | |
| Bosica et al. | Aza-Michael reaction: selective mono-versus bis-addition under environmentally-friendly conditions | |
| CN113307778A (en) | Preparation method of 3-trifluoromethyl substituted 1,2, 4-triazole compound | |
| RU2474583C2 (en) | Method of producing bicyclic guanidines using cyclic thiourea | |
| Reddy et al. | Di-n-butyl ammonium chlorosulfonate ionic liquids as an efficient and recyclable catalyst for the synthesis of 1, 4-dihydrobenzo [4, 5] imidazo [1, 2-a] pyrimidine-3-carboxylates under solvent-free ultrasound irradiation | |
| CN114621149A (en) | Method for synthesizing indazole compound by MOF-H248 catalysis | |
| CN106000465A (en) | Method for oxidative coupling reaction of aldehyde and secondary amide | |
| CN112661584B (en) | Preparation method of photocatalytic N-alkyl amide compound | |
| CN102977097A (en) | Aryne-based substituted indolizine derivative and preparation method and applications thereof | |
| CN105646382A (en) | Preparation method of 1,3,5-trisubstituted 1,2,4-triazole compound | |
| CN110372774A (en) | The alpha-acyloxy amides dipeptides analog derivative and synthetic method that isoindolone replaces | |
| CN106111190B (en) | A kind of chirality biaryl skeleton pyridoxamine class catalyst and its synthetic method and application | |
| CN109705036A (en) | Fluorine-containing quinoline amides folded formation, preparation method and chiral Recognition methods and applications | |
| CN108069868B (en) | Method for preparing organic amide compound from aryl diazo tetrafluoroborate and nitrile | |
| CN113087667B (en) | Synthesis method of imidazolidinone derivative | |
| CN110372567A (en) | Chain cyclic dipeptide analog derivative and preparation method thereof of the one kind containing sulfonyl | |
| CN105175352A (en) | Preparation method of nitazoxanide | |
| CN108383754A (en) | The preparation method and application of a kind of aryl oxime compound | |
| CN112778184B (en) | Method for arylating alpha position of tertiary amine | |
| CN109761917A (en) | Isolonglifolane ketone group -2- Aminopyrimidines boron trifluoride fluorescence probe and its synthetic method and application | |
| CN109251192A (en) | 3 or 4 position trifluoromethyls replace the preparation method of isocoumarin |
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 | ||
| RJ01 | Rejection of invention patent application after publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20190927 |