CN109369559A - Using DMF as one step of carbon source construct 2-(4- xenyl) -1,3,4- oxadiazoles method - Google Patents
Using DMF as one step of carbon source construct 2-(4- xenyl) -1,3,4- oxadiazoles method Download PDFInfo
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- CN109369559A CN109369559A CN201811341550.4A CN201811341550A CN109369559A CN 109369559 A CN109369559 A CN 109369559A CN 201811341550 A CN201811341550 A CN 201811341550A CN 109369559 A CN109369559 A CN 109369559A
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- xenyl
- oxadiazoles
- dmf
- carbon source
- oxidant
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- 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
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- 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- xenyl) -1,3,4- oxadiazoles method.This method is using 4- biphenyl carboxylic acid hydrazine as reaction raw materials, with DMF(N, dinethylformamide) it is used as carbon source through carbon cyclization, a step constructs 2-(4- xenyl) -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- xenyl) -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 4- biphenyl carboxylic acid hydrazine as reaction raw materials, mild
Reaction condition constructs 2-(4- xenyl in next step) -1,3,4- oxadiazoles.
The 2-(4- xenyl 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- xenyl) -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- biphenyl
Base) -1,3,4- oxadiazoles method.
Specific steps are as follows:
Raw material is weighed according to following molar ratio, catalyst: oxidant: 4- biphenyl carboxylic acid hydrazine=0.05 ~ 0.5:1 ~ 4:1；It will claim
The raw material taken is placed in reaction vessel, is added solvent n,N-Dimethylformamide (DMF), and carbocyclic ring is carried out at 40 ~ 150 DEG C
Reaction 1 ~ 72 hour；Products therefrom is isolated and purified using column chromatography, and column chromatographic eluate is the mixed of petroleum ether and ethyl acetate
Liquid is closed, wherein the volume ratio of petroleum ether and ethyl acetate is 1 ~ 40:1, after isolating and purifying, obtains 2-(4- xenyl) -1,3,
4- oxadiazoles.
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- xenyl) -1,3,4- oxadiazoles nuclear magnetic resonance spectroscopy.
Fig. 3 be the embodiment of the present invention 1 obtained in 2-(4- xenyl) -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 the 4- biphenyl carboxylic acid hydrazine of addition in the test tube of 25 mL, 0.05 mM of cuprous iodide, potassium peroxydisulfate 0.2
MM, DMF(N, dinethylformamide is added) it is used as solvent, it is stirred at 120 DEG C.TLC(thin-layered chromatography) detection is instead
Reaction solution is cooled to room temperature, reaction solution filtering, extraction, filtrate decompression revolving removal solvent after answering, then is chromatographed by column
Isolate and purify, obtain target product 2-(4- xenyl) -1,3,4- oxadiazoles, it is 3 that column chromatographic eluate used, which is volume ratio:
1 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 the 4- biphenyl carboxylic acid hydrazine of addition in the test tube of 25 mL, 0.05 mM of cuprous iodide, t-butyl peroxy
Change 0.2 mM of hydrogen, DMF(N, dinethylformamide be added) it is used as solvent, it is stirred at 120 DEG C.TLC(thin-layer chromatography
Method) tracing detection, do not detect target product.
Comparative example 2:
0.2 mM of 4- biphenyl carboxylic acid hydrazine is added in the test tube of 25 mL, 0.05 mM of cuprous iodide, silver carbonate 0.2 is in the least
Mole, DMF(N, dinethylformamide is added) it is used as solvent, it is stirred under 120 degrees Celsius.TLC(thin-layered chromatography) tracking
Detection, does not detect target product.
Comparative example 3:
0.2 mM of 4- biphenyl carboxylic acid hydrazine is added in the test tube of 25 mL, 0.05 mM of cuprous iodide, silver nitrate 0.2 is in the least
Mole, DMF(N, dinethylformamide is added) it is used as solvent, it is stirred under 120 degrees Celsius.TLC(thin-layered chromatography) tracking
Detection, does not detect target product.
Comparative example 4:
0.2 mM of 4- biphenyl carboxylic acid hydrazine is added in the test tube of 25 mL, 0.05 mM of cuprous iodide, silver oxide 0.2 is in the least
Mole, DMF(N, dinethylformamide is added) it is used as solvent, it is stirred under 120 degrees Celsius.TLC(thin-layered chromatography) tracking
Detection, 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 4- biphenyl carboxylic acid hydrazine, and raw material is simple and easy to get, and the target of generation produces
Object 1,3,4- oxadiazoles are then the star molecules of drug field, which is that the synthesis of 1,3,4- furodiazole compounds mentions
New Research Thinking is supplied.
Claims (1)
1. a kind of construct 2-(4- xenyl 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: 4- biphenyl carboxylic acid hydrazine=0.05 ~ 0.5:1 ~ 4:1；It will weigh
Raw material be placed in reaction vessel, be added solvent n,N-Dimethylformamide, at 40 ~ 150 DEG C carry out carbon cyclization 1 ~ 72
Hour；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- xenyl) -1,3,4- oxadiazoles；
The catalyst is cuprous iodide；
The oxidant is potassium peroxydisulfate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811341550.4A CN109369559A (en) | 2018-11-12 | 2018-11-12 | Using DMF as one step of carbon source construct 2-(4- xenyl) -1,3,4- oxadiazoles method |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811341550.4A CN109369559A (en) | 2018-11-12 | 2018-11-12 | Using DMF as one step of carbon source construct 2-(4- xenyl) -1,3,4- oxadiazoles method |
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| Publication Number | Publication Date |
|---|---|
| CN109369559A true CN109369559A (en) | 2019-02-22 |
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| CN201811341550.4A Withdrawn CN109369559A (en) | 2018-11-12 | 2018-11-12 | Using DMF as one step of carbon source construct 2-(4- xenyl) -1,3,4- oxadiazoles method |
Country Status (1)
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2018
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Application publication date: 20190222 |