CN108558974A - A kind of preparation and application of the derivative pyridine triazole Raney nickel of sugar - Google Patents
A kind of preparation and application of the derivative pyridine triazole Raney nickel of sugar Download PDFInfo
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- CN108558974A CN108558974A CN201810411978.5A CN201810411978A CN108558974A CN 108558974 A CN108558974 A CN 108558974A CN 201810411978 A CN201810411978 A CN 201810411978A CN 108558974 A CN108558974 A CN 108558974A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H23/00—Compounds containing boron, silicon, or a metal, e.g. chelates, vitamin B12
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- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
- B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
- B01J31/1815—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine with more than one complexing nitrogen atom, e.g. bipyridyl, 2-aminopyridine
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
- B01J2531/0213—Complexes without C-metal linkages
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
- B01J2531/0238—Complexes comprising multidentate ligands, i.e. more than 2 ionic or coordinative bonds from the central metal to the ligand, the latter having at least two donor atoms, e.g. N, O, S, P
- B01J2531/0241—Rigid ligands, e.g. extended sp2-carbon frameworks or geminal di- or trisubstitution
- B01J2531/0244—Pincer-type complexes, i.e. consisting of a tridentate skeleton bound to a metal, e.g. by one to three metal-carbon sigma-bonds
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/84—Metals of the iron group
- B01J2531/847—Nickel
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Abstract
The invention discloses one kind acyl glucose pyridine triazole Raney nickel as shown in formula (3)；In formula (3), R is one kind in acetyl group, pivaloyl group.And the preparation method of acyl glucose pyridine triazole Raney nickel is disclosed, and its application in Acetanilide Derivatives preparation.It is an advantage of the invention that：Novel acyl group grape pyridine triazole Raney nickel has been synthesized for the first time, and has been applied in the catalyzing and synthesizing of acetylbenzene aminated compounds.Compared with traditional handicraft, preparation method of the present invention has easy to operate, the advantages such as three wastes discharge amount is few, and production cost is low, is a kind of economic, environmental protection production technology.
Description
Technical field
The invention belongs to organometallic catalytic field, it is related to a kind of acyl glucose pyridine triazole Raney nickel and its system
Preparation Method, and its application in Acetanilide Derivatives synthesis.
Background technology
Antifebrin is a kind of important chemical substance, is had in materials chemistry, in biological medicine and organic synthesis extensive
Purposes.For example, in the important drug molecular structure such as scheme for lacosamide, benorylate, chloramphenicol, all contain antifebrin structure piece
Section.Therefore, developing the novel synthesis of antifebrin is particularly important.The method that tradition prepares antifebrin mainly has：1.
The condensation between acetic acid and aniline is realized by using the condensing agent of stoichiometry；2. using dangerous higher chloroacetic chloride and benzene
Amine prepares antifebrin.However, the shortcomings of that there are Atom economies is poor for these methods, and operational danger is high.With science skill
The progress of art and economic rapid development, this environmentally protective themes of the times are rooted in the hearts of the people.Therefore, it finds efficient, energy saving, safe
Methodology of organic synthesis be always focus of people's attention.In recent years, the development of transition metal-catalyzed organic synthesis is just catered to
This Times ' Demand, and prepare cheap, efficient, nontoxic orgnometallic catalyst be push the development of this field emphasis and
Difficult point.Saccharide compound is the ideal for synthesizing orgnometallic catalyst ligand as biomass a kind of cheap and easy to get and nontoxic
Raw material.Therefore, synthesizing new glycosyl metallic catalyst has great importance.
Invention content
An object of the present invention is to provide a kind of preparation method and acyl of acyl group grape pyridine triazole Raney nickel
Application of the base grape pyridine triazole Raney nickel in synthesizing Acetanilide Derivatives.
The present invention provides a kind of nickel ligand catalyst with following structural,
Wherein, R is one kind in acetyl group, pivaloyl group.Preferably, the R is acetyl group.
The present invention also provides a kind of preparation sides of the acyl group grape pyridine triazole Raney nickel of structural formula as indicated at 3
Method.One, it by appropriate nitrine acyl glucose 1, is dissolved in solvent X, 2- pyridinium acetylenes, copper sulphate and the different Vitamin Cs of D- is then added
Sour sodium, gentle agitation 12 hours, obtain acyl glucose pyridine triazole by recrystallizing methanol after reaction at room temperature
2.Two, appropriate acyl glucose pyridine triazole 2 is taken, is dissolved in solvent Y, nickel chloride is added, gentle agitation 12 is small at room temperature
When.Wait for that, after reaction through filtering, washing is dried to obtain acyl group grape pyridine triazole Raney nickel 3.
In the acyl group grape pyridine triazole Raney nickel preparation process, solvent X described in reaction step one is dichloro
Methane, 1,2- dichloroethanes, the tert-butyl alcohol, tetrahydrofuran, the preferably tert-butyl alcohol；The two solvent Y are dichloromethane in reaction step
Alkane, acetonitrile, toluene, preferably toluene.The molar ratio of acyl glucose pyridine triazole and nickel chloride is 1.1: 0.5.It is described anti-
It is 12 hours that TLC tracing detections, usual first step reaction time, which should be used, and the second step reaction time is 12 hours.
The purity grade of the solvent involved in the present invention arrived is chemical pure (CP) or more, and chemical reagent is purchased from An Naiji reagents
Co., Ltd, nitrine acyl glucose press document Green Chem., and disclosed in 2015,17,225 prepared by method.
The preparation route of acyl group grape pyridine triazole Raney nickel of the present invention is as follows：
The present invention provides acyl group grape pyridine triazole Raney nickel Acetanilide Derivatives preparation in application,
It is to use following methods：
Be added in reaction tube amino benzenes compounds, acyl glucose pyridine triazole Raney nickel, imidazoles and solvent (N,
N- dimethylacetylamides: water), it reacts 6 hours in a heated condition.It waits for that after reaction, reaction solution being cooled to room temperature, through extraction
It takes, crossing column purification after dry obtains Acetanilide Derivatives.
In the Acetanilide Derivatives preparation process, the molar ratio of aniline and imidazoles is 1: (2-5) is preferred, preferably
1∶3；The molar ratio of aniline and acyl group grape pyridine triazole Raney nickel is 1: (0.0005-0.005) is preferred, preferably 1:
0.001；N,N-dimethylacetamide and the volume ratio of water are 1: (0.5-2) is preferred, preferably 1: 1.
The route that acyl group grape pyridine triazole Raney nickel of the present invention catalyzes and synthesizes Acetanilide Derivatives is as follows：
It is an advantage of the invention that：Novel acyl group grape pyridine triazole Raney nickel has been synthesized for the first time, and has been applied to
In the catalyzing and synthesizing of acetylbenzene aminated compounds.Compared with traditional handicraft, preparation method of the present invention has easy to operate, the three wastes
The advantages such as discharge capacity is few, and production cost is low are a kind of economic, environmental protection production technologies.
Specific implementation mode
Invention is described further with reference to specific embodiment, but the protection domain invented is not limited to this.Ability
The those of ordinary skill in domain can with and should know that any simple change based on true spirit or replacement should all belong to
In protection domain of the presently claimed invention.
Embodiment 1 (preparation of acetyl group glucose pyridine triazole Raney nickel)
A), the synthesis of acetyl group glucose pyridine triazole 2a
1 mM of acetyl azide glucose 1a is weighed, is dissolved in 5 milliliters of tert-butyl alcohols, 1 mM of 2- acetylene is then added
Pyridine, 18 milligrams of copper sulphate, 40 milligrams of D-araboascorbic acid sodium, gentle agitation 12 hours, (stone is detected by TLC at room temperature
Oily ether: ethyl acetate=1: 1) monitoring reaction.It waits for after reaction, 5 milliliters of dichloromethane extractions being added, decompression is spin-dried for, obtains
Go out product recrystallizing methanol, obtain acetyl group glucosyl group pyridine triazole 2a.Yield is 93%；214-215 DEG C of fusing point
。1H NMR(500MHz. DMSO)：δ 9.00 (s, 1H), 8.64 (d, J=4Hz, 1H), 8.05 (d, J=8Hz, 1H), 7.93
(td, J=7.8,1.5Hz, 1H), 7.39 (dd, J=6.9,5.3Hz, 1H), 6.44 (d, J=9.2Hz, 1H), 5.80 (t, J=
9.4 Hz, 1H), 5.62 (t, J=9.5Hz, 1H), 5.25 (t, J=9.8Hz, 1H), 4.41 (ddd, J=10.0,5.5,2.4
Hz, 1H), 4.13 (qd, J=12.5,3.9Hz, 2H), 2.05 (s, 3H), 2.01 (s, 3H), 1.99 (s, 3H), 1.82 (s,
3H).13C NMR (126MHz, DMSO)：δ 170.55,170.08,169.90,169.14,150.24,149.73,148.31,
137.82,123.87,122.76,120.10,84.52,73.70,72.45,70.66,67.95,62.35,20.99,20.89,
20.74 20.40.
B), the synthesis of acetyl group glucose pyridine triazole Raney nickel 3a
1.1 mMs of acetyl group glucose pyridine triazole 2a are weighed, are dissolved in 5 milliliters of toluene, 0.5 Bo mole chlorine is added
Change nickel, at room temperature gentle agitation 12 hours, passes through TLC detections (petroleum ether: ethyl acetate=1: 1) monitoring is reacted.It waits reacting
After filter, first washed 3 times with cold toluene, then washed 3 times with ether, obtained solid is dried in 30 DEG C of vacuum tank,
Obtain acetyl group glucose pyridine triazole Raney nickel 3a.
Embodiment 2 (preparations of Acetanilide Derivatives)
1 mM of aniline is added in 25 milliliters of reaction tubes, 0.001 mM of acetyl group glucose pyridine triazole nickel is urged
Agent 3a, 3 mMs of imidazoles and 2 milliliters of solvents (in 1), 6 water=1: n,N-dimethylacetamide: are heated under 140 degrees Celsius
Hour.The reaction process carries out qualitative monitoring with thin-layer chromatography (TLC), waits for that after reaction, reaction solution being cooled to room temperature, adds
Enter water and ethyl acetate, takes organic layer, anhydrous Na2SO4It is dry, merge organic phase, Rotary Evaporators is used in combination to remove reaction dissolvent,
Crude product isolated and purified with column chromatography (ethyl acetate: petroleum ether=1: 10), yield 86%；1H NMR (500MHz,
CDCl3) δ 7.50 (d, J=7.9Hz, 2H), 7.36 (s, 1H), 7.31 (t, J=7.9Hz, 2H), 7.10 (t, J=7.4Hz,
1H), 2.17 (s, 3H)
Embodiment 3 (preparation of pivaloyl group glucose pyridine triazole Raney nickel)
A), the synthesis of pivaloyl group glucose pyridine triazole 2b
1 mM of nitrine pivaloyl group glucose 1b is weighed, is dissolved in 5 milliliters of tert-butyl alcohols, 1 mM of 2- second is then added
Alkynes pyridine, 18 milligrams of copper sulphate, 40 milligrams of D-araboascorbic acid sodium, gentle agitation 12 hours, are detected by TLC at room temperature
(petroleum ether: ethyl acetate=1: 1) monitoring reaction.It waits for after reaction, 5 milliliters of dichloromethane extractions being added, decompression is spin-dried for, obtains
To go out product recrystallizing methanol, obtain pivaloyl group glucose pyridine triazole 2b.Yield is 96%；Fusing point 227-228
℃。1H NMR (500MHz, DMSO)：δ 9.02 (s, 1H), 8.64 (d, J=4.3Hz, 1H), 8.02 (d, J=7.8Hz, 1H),
7.92 (d, J=7.4Hz, 1H), 7.48-7.22 (m, 1H), 6.46 (d, J=9.2Hz, 1H), 5.83 (t, J=9.3Hz, 1H),
5.68 (t, J=9.5Hz, 1H), 5.36 (t, J=9.8Hz, 1H), 4.50 (d, J=10.0Hz, 1H), 4.14 (d, J=
2.0Hz, 2H), 1.15 (s, 8H), 1.13 (s, 9H), 1.07 (s, 9H), 0.84 (s, 9H)13C NMR (126MHz, DMSO)：δ
177.52,176.85,176.21,176.01,150.23,148.29,137.75,123.79,122.87,120.14,84.92,
74.20,72.52,70.71,67.38,61.67,38.79,38.76,38.71,38.56,27.23,27.11.26.77.
B), the synthesis of pivaloyl group glucose pyridine triazole Raney nickel 3b
1.1 mMs of pivaloyl group glucose pyridine triazole 2b are weighed, are dissolved in 5 milliliters of toluene, 0.5 mmoles are added
That nickel chloride, gentle agitation 12 hours, pass through TLC detections (petroleum ether: ethyl acetate=1: 1) monitoring is reacted at room temperature.It waits for
It filters, is first washed 3 times with cold toluene after reaction, then washed 3 times with ether, obtained solid dries in 30 DEG C of vacuum tank
It is dry, obtain pivaloyl group glucose pyridine triazole Raney nickel 3b.
Embodiment 4 (preparations of Acetanilide Derivatives)
1 mM of aniline, 0.001 mM of pivaloyl group glucose pyridine triazole nickel are added in 25 milliliters of reaction tubes
Catalyst 3b, 3 mMs of imidazoles and 2 milliliters of solvents (n,N-dimethylacetamide: water=1: in 1), heat under 140 degrees Celsius
6 hours.The reaction process carries out qualitative monitoring with thin-layer chromatography (TLC), waits for that after reaction, reaction solution being cooled to room temperature,
Water and ethyl acetate is added, takes organic layer, anhydrous Na2SO4It is dry, merge organic phase, is used in combination Rotary Evaporators to remove dereaction molten
Agent, crude product isolated and purified with column chromatography (ethyl acetate: petroleum ether=1: 10), yield 78%.
Fig. 1 is the mass spectrogram of the derivative pyridine triazole Raney nickel of sugar
Claims (5)
1. a kind of acyl glucose pyridine triazole Raney nickel as shown in formula (3)；
In formula (3), R is one kind in acetyl group, pivaloyl group.
2. the preparation method of acyl glucose pyridine triazole Raney nickel described in claim 1 is by appropriate nitrine acyl group
Glucose is dissolved in solvent X, 2- pyridinium acetylenes, copper sulphate and D-araboascorbic acid sodium is then added, at room temperature gentle agitation
12 hours, acyl glucose pyridine triazole is obtained by recrystallizing methanol after reaction.Later, appropriate acyl glucose is taken
Pyridine triazole is dissolved in solvent Y, nickel chloride is added, at room temperature gentle agitation 12 hours.It waits for after reaction through filtering,
Washing is dried to obtain acyl group grape pyridine triazole Raney nickel.
3. the preparation method of acyl glucose pyridine triazole Raney nickel described in claim 2, which is characterized in that reaction step
Solvent X described in one is dichloromethane, 1,2- dichloroethanes, the tert-butyl alcohol, tetrahydrofuran, the preferably tert-butyl alcohol；In reaction step
The two solvent Y are dichloromethane, acetonitrile, toluene, preferably toluene.Mole of acyl glucose pyridine triazole and nickel chloride
Than being 1.1: 0.5.
4. application of the acyl group grape pyridine triazole Raney nickel described in claim 1 in Acetanilide Derivatives preparation,
It is characterized in that, using following methods：It is added in reaction tube amino benzenes compounds, the catalysis of acyl glucose pyridine triazole nickel
Agent, imidazoles and solvent (n,N-dimethylacetamide：Water), it reacts 6 hours in a heated condition.It waits for after reaction, to react
Liquid is cooled to room temperature, and crossing column purification through extraction, after dry obtains Acetanilide Derivatives.
5. application of the acyl group grape pyridine triazole Raney nickel described in claim 4 in Acetanilide Derivatives preparation,
It is characterized in that the molar ratio of aniline and imidazoles is 1 in reaction process: (2-5) is preferred, preferably 1: 3；Aniline and acyl group grape
The molar ratio of pyridine triazole Raney nickel is 1: (0.0005-0.005) is preferred, preferably 1: 0.001；N, N- dimethylacetamide
The volume ratio of amine and water is 1: (0.5-2) is preferred, preferably 1: 1.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110423260A (en) * | 2019-07-12 | 2019-11-08 | 中山大学 | A kind of Cyclometalated iridium photosensitizer of glucose modified and its preparation method and application |
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| CN104761601A (en) * | 2015-03-09 | 2015-07-08 | 江苏师范大学 | Synthesis and uses of beta-1-imidazole-2,3,4,6-tetrasulfo-D-glucopyranose hydrosulfate |
| CN105131058A (en) * | 2015-07-01 | 2015-12-09 | 杭州师范大学 | 3- glucamine-5-phenyl-1,2,4-triazole derivative and preparation method and uses thereof |
| EP3838909A1 (en) * | 2019-12-16 | 2021-06-23 | Galecto Biotech AB | Large scale process for the preparation of 5-bromopyridin-3-yl-3-deoxy-3-[4-(3,4,5-trifluorophenyl)-1h-1,2,3-triazol-1-yl]- 1-thio-alpha-d-galactopyranoside |
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Patent Citations (3)
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| CN104761601A (en) * | 2015-03-09 | 2015-07-08 | 江苏师范大学 | Synthesis and uses of beta-1-imidazole-2,3,4,6-tetrasulfo-D-glucopyranose hydrosulfate |
| CN105131058A (en) * | 2015-07-01 | 2015-12-09 | 杭州师范大学 | 3- glucamine-5-phenyl-1,2,4-triazole derivative and preparation method and uses thereof |
| EP3838909A1 (en) * | 2019-12-16 | 2021-06-23 | Galecto Biotech AB | Large scale process for the preparation of 5-bromopyridin-3-yl-3-deoxy-3-[4-(3,4,5-trifluorophenyl)-1h-1,2,3-triazol-1-yl]- 1-thio-alpha-d-galactopyranoside |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110423260A (en) * | 2019-07-12 | 2019-11-08 | 中山大学 | A kind of Cyclometalated iridium photosensitizer of glucose modified and its preparation method and application |
| CN110423260B (en) * | 2019-07-12 | 2022-08-02 | 中山大学 | Glucose-modified cyclometalated iridium photosensitizer and preparation method and application thereof |
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