CN109336840A - Using DMF as one step of carbon source construct 2-(4- fluorophenyl) -1,3,4- oxadiazoles method - Google Patents
Using DMF as one step of carbon source construct 2-(4- fluorophenyl) -1,3,4- oxadiazoles method Download PDFInfo
- Publication number
- CN109336840A CN109336840A CN201811341586.2A CN201811341586A CN109336840A CN 109336840 A CN109336840 A CN 109336840A CN 201811341586 A CN201811341586 A CN 201811341586A CN 109336840 A CN109336840 A CN 109336840A
- Authority
- CN
- China
- Prior art keywords
- fluorophenyl
- oxadiazoles
- dmf
- carbon source
- oxidant
- 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.)
- Withdrawn
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
The invention discloses one kind with DMF(N, dinethylformamide) be one step of carbon source construct 2-(4- fluorophenyl) -1,3,4- oxadiazoles method.This method is using p-fluorobenzoyl hydrazide as reaction raw materials, with DMF(N, dinethylformamide) it is used as carbon source through carbon cyclization, a step constructs 2-(4- fluorophenyl) -1,3,4- oxadiazoles.The method of the present invention synthesizing mean is novel, and reaction condition is mild, meets the demand for development of Green Chemistry.
Description
Technical field
The invention belongs to the technical fields such as medicine, material, cell biology, and in particular to DMF(N, N- dimethyl methyl
Amide) be one step of carbon source construct 2-(4- fluorophenyl) -1,3,4- oxadiazoles method.
Background technique
1,3,4- oxadiazoles and its derivative are a kind of important physiological activators, have certain anti-inflammatory, antibacterial, resist
Cancer, anti-AIDS and coordinate plant growth isoreactivity, certain 1,3,4- furodiazole compounds are also important photoactive substance, have
Optical activity can be used as photosensitive macromolecular material applied to electroluminescence instrument.The drug for hypertension tiodazosin listed
With the structural unit in Nesapidil all containing 1,3,4- oxadiazoles.Therefore, to the synthesis one of 1,3,4- furodiazole compound
It has all been the research hotspot of chemist since straight.Its traditional synthetic method will often use toxic chemical reagent, such as trichlorine oxygen
Phosphorus etc..The present invention is with DMF(N, dinethylformamide) it is carbon source, using p-fluorobenzoyl hydrazide as reaction raw materials, mild anti-
Condition is answered to construct 2-(4- fluorophenyl in next step) -1,3,4- oxadiazoles.
The 2-(4- fluorophenyl that the present invention synthesizes) -1,3,4- oxadiazoles, structural formula is as follows:
。
With DMF(N, dinethylformamide) be that one step of carbon source constructs 2-(4- fluorophenyl) -1, the method for 3,4- oxadiazoles,
New synthesis path is provided for the synthesis of such compound, because of its simple synthetic line, there is huge application value.
Summary of the invention
The object of the present invention is to provide one kind with DMF(N, dinethylformamide) it is that one step of carbon source constructs 2-(4- fluorobenzene
Base) -1,3,4- oxadiazoles method.
Specific steps are as follows:
Raw material is weighed according to following molar ratio, catalyst: oxidant: p-fluorobenzoyl hydrazide=0.05 ~ 0.5:1 ~ 4:1；It will be weighed
Raw material is placed in reaction vessel, is added solvent n,N-Dimethylformamide (DMF), and carbon cyclization 1 is carried out at 40 ~ 150 DEG C
~ 72 hours；Products therefrom is isolated and purified using column chromatography, and column chromatographic eluate is the mixed liquor of petroleum ether and ethyl acetate,
Wherein the volume ratio of petroleum ether and ethyl acetate is 1 ~ 40:1, after isolating and purifying, obtains 2-(4- fluorophenyl) -1,3,4- evils two
Azoles.
The catalyst is cuprous iodide.
The oxidant is potassium peroxydisulfate.
The method of the present invention has the advantage that
(1) reaction condition is mild.
(2) reaction raw materials are simple and easy to get, green safe.
(3) synthetic route is novel.
Detailed description of the invention
Fig. 1 is the synthetic route chart of the method for the present invention.
Fig. 2 be the embodiment of the present invention 1 obtained in 2-(4- fluorophenyl) -1,3,4- oxadiazoles nuclear magnetic resonance spectroscopy.
Fig. 3 be the embodiment of the present invention 1 obtained in 2-(4- fluorophenyl) -1,3,4- oxadiazoles carbon-13 nmr spectra.
Specific embodiment
The invention is further described below by specific embodiment.
Embodiment 1:
0.2 mM of p-fluorobenzoyl hydrazide is added in the test tube of 25 mL, 0.05 mM of cuprous iodide, potassium peroxydisulfate 0.2 is in the least
Mole, DMF(N, dinethylformamide is added) it is used as solvent, it is stirred at 120 DEG C.TLC(thin-layered chromatography) detection reaction
After reaction solution is cooled to room temperature, reaction solution filtering, extraction, filtrate decompression revolving removal solvent, then divided by column chromatography
From purifying, target product 2-(4- fluorophenyl is obtained) -1,3,4- oxadiazoles, it is 3:1 that column chromatographic eluate used, which is volume ratio,
Petroleum ether: ethyl acetate mixtures, yield 60%.
The present embodiment structure of title compound is shown in Fig. 2 and Fig. 3.
Comparative example 1:
0.2 mM of p-fluorobenzoyl hydrazide of the addition in the test tube of 25 mL, 0.05 mM of cuprous iodide, tert-butyl hydroperoxide
0.2 mM of hydrogen, DMF(N, dinethylformamide is added) it is used as solvent, it is stirred at 120 DEG C.TLC(thin-layered chromatography)
Tracing detection does not detect target product.
Comparative example 2:
0.2 mM of p-fluorobenzoyl hydrazide of the addition in the test tube of 25 mL, 0.05 mM of cuprous iodide, 0.2 mmoles of silver carbonate
You, is added DMF(N, dinethylformamide) it is used as solvent, it is stirred under 120 degrees Celsius.TLC(thin-layered chromatography) tracking inspection
It surveys, does not detect target product.
Comparative example 3:
0.2 mM of p-fluorobenzoyl hydrazide of the addition in the test tube of 25 mL, 0.05 mM of cuprous iodide, 0.2 mmoles of silver nitrate
You, is added DMF(N, dinethylformamide) it is used as solvent, it is stirred under 120 degrees Celsius.TLC(thin-layered chromatography) tracking inspection
It surveys, does not detect target product.
Comparative example 4:
0.2 mM of p-fluorobenzoyl hydrazide of the addition in the test tube of 25 mL, 0.05 mM of cuprous iodide, 0.2 mmoles of silver oxide
You, is added DMF(N, dinethylformamide) it is used as solvent, it is stirred under 120 degrees Celsius.TLC(thin-layered chromatography) tracking inspection
It surveys, does not detect target product.
In above-described embodiment, oxidant species have a significant impact reaction effect, and concrete outcome is shown in Table 1.
Table 1
| Example | Oxidant(oxidant) | Yield (%) |
| Embodiment 1 | Potassium peroxydisulfate | 60 |
| Comparative example 1 | Tert-butyl hydroperoxide | 0 |
| Comparative example 2 | Silver carbonate | 0 |
| Comparative example 3 | Silver nitrate | 0 |
| Comparative example 4 | Silver oxide | 0 |
The present invention has apparent oxidant specificity, can just detect when only using potassium peroxydisulfate as oxidant accordingly
Target product；In addition to this, reaction raw materials of the invention are p-fluorobenzoyl hydrazide, and raw material is simple and easy to get, the target product of generation
1,3,4- oxadiazoles is then the star molecule of drug field, which is that the synthesis of 1,3,4- furodiazole compounds provides
New Research Thinking.
Claims (1)
1. a kind of construct 2-(4- fluorophenyl by one step of carbon source of DMF) -1, the method for 3,4- oxadiazoles, it is characterised in that specific step
Suddenly are as follows:
Raw material is weighed according to following molar ratio, catalyst: oxidant: p-fluorobenzoyl hydrazide=0.05 ~ 0.5:1 ~ 4:1；It will be weighed
Raw material is placed in reaction vessel, and solvent n,N-Dimethylformamide is added, and it is small that carbon cyclization 1 ~ 72 is carried out at 40 ~ 150 DEG C
When；Products therefrom is isolated and purified using column chromatography, and column chromatographic eluate is the mixed liquor of petroleum ether and ethyl acetate, wherein stone
The volume ratio of oily ether and ethyl acetate is 1 ~ 40:1, after isolating and purifying, obtains 2-(4- fluorophenyl) -1,3,4- oxadiazoles；
The catalyst is cuprous iodide；
The oxidant is potassium peroxydisulfate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811341586.2A CN109336840A (en) | 2018-11-12 | 2018-11-12 | Using DMF as one step of carbon source construct 2-(4- fluorophenyl) -1,3,4- oxadiazoles method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811341586.2A CN109336840A (en) | 2018-11-12 | 2018-11-12 | Using DMF as one step of carbon source construct 2-(4- fluorophenyl) -1,3,4- oxadiazoles method |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN109336840A true CN109336840A (en) | 2019-02-15 |
Family
ID=65315094
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201811341586.2A Withdrawn CN109336840A (en) | 2018-11-12 | 2018-11-12 | Using DMF as one step of carbon source construct 2-(4- fluorophenyl) -1,3,4- oxadiazoles method |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN109336840A (en) |
-
2018
- 2018-11-12 CN CN201811341586.2A patent/CN109336840A/en not_active Withdrawn
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Kamal et al. | Enantioselective ring opening of epoxides with trimethylsilyl azide (TMSN3) in the presence of β-cyclodextrin: an efficient route to 1, 2-azido alcohols | |
| CN104326892A (en) | Synthetic method of indanone by gold-catalysis | |
| CN108191919B (en) | - 2 (1H) -one of 4- (substituted-phenyl) -6- ferrocenyl -3,4- dihydro-pyrimidin and preparation method thereof | |
| Jovanović et al. | Acid-Catalyzed [3+ 2] Cycloaddition of Enones with Azomethine Imines for Easy Access to Tetrahydropyrazolopyrazolones | |
| CN109336840A (en) | Using DMF as one step of carbon source construct 2-(4- fluorophenyl) -1,3,4- oxadiazoles method | |
| CN109232463A (en) | Using DMF as one step of carbon source construct 2-(4- bromophenyl) -1,3,4- oxadiazoles method | |
| CN109369561A (en) | Using DMF as one step of carbon source construct 2-(4- chlorphenyl) -1,3,4- oxadiazoles method | |
| CN109206418A (en) | Using DMF as one step of carbon source construct 2-(2- furyl) -1,3,4- oxadiazoles method | |
| CN109369560A (en) | Using DMF as one step of carbon source construct 2-(3- chlorphenyl) -1,3,4- oxadiazoles method | |
| CN109232462A (en) | Using DMF as one step of carbon source construct 2-(1- naphthalene) -1,3,4- oxadiazoles method | |
| CN109293650A (en) | Using DMF as one step of carbon source construct 2-(2- thienyl) -1,3,4- oxadiazoles method | |
| CN113072520B (en) | C2 substituted 2H-benzothiazole aryl acylation derivative and synthesis method and application thereof | |
| CN109336839A (en) | Using DMF as one step of carbon source construct 2-(3- tolyl) -1,3,4- oxadiazoles method | |
| CN109251185A (en) | The method for constructing 2- phenyl -1,3,4- oxadiazoles as one step of carbon source using DMF | |
| CN109369559A (en) | Using DMF as one step of carbon source construct 2-(4- xenyl) -1,3,4- oxadiazoles method | |
| CN109232461A (en) | Using DMF as one step of carbon source construct 2-(2- tolyl) -1,3,4- oxadiazoles method | |
| CN109336841A (en) | Using DMF as one step of carbon source construct 2-(4- nitrobenzophenone) -1,3,4- oxadiazoles method | |
| CN109206382A (en) | Using DMF as one step of carbon source construct 2-(4- tert-butyl-phenyl) -1,3,4- oxadiazoles method | |
| CN106397381B (en) | 2- alkoxy chromone 9 oxime derivate and the preparation method and application thereof | |
| CN109293594A (en) | Using DMF as one step of carbon source construct 2-(4- methoxyphenyl) -1,3,4- oxadiazoles method | |
| CN109336837A (en) | Using DMF as one step of carbon source construct 2-(4- cyano-phenyl) -1,3,4- oxadiazoles method | |
| CN109336838A (en) | The method for constructing 2- p-methylphenyl -1,3,4- oxadiazoles as one step of carbon source using DMF | |
| CN109160905A (en) | Using DMF as one step of carbon source construct 2-(4- trifluoromethyl) -1,3,4- oxadiazoles method | |
| CN109336880A (en) | 2-(3,4- methylenedioxyphenyl are constructed by one step of carbon source of DMF) -1, the method for 3,4- oxadiazoles | |
| CN111635401A (en) | Copper complex promoted 7-fluoroimidazo [1,2-a ] pyridine synthesis method |
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 | ||
| WW01 | Invention patent application withdrawn after publication |
Application publication date: 20190215 |
|
| WW01 | Invention patent application withdrawn after publication |