CN109251185A - The method for constructing 2- phenyl -1,3,4- oxadiazoles as one step of carbon source using DMF - Google Patents
The method for constructing 2- phenyl -1,3,4- oxadiazoles as one step of carbon source using DMF Download PDFInfo
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- CN109251185A CN109251185A CN201811341557.6A CN201811341557A CN109251185A CN 109251185 A CN109251185 A CN 109251185A CN 201811341557 A CN201811341557 A CN 201811341557A CN 109251185 A CN109251185 A CN 109251185A
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- oxadiazoles
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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) it is the method that one step of carbon source constructs 2- phenyl -1,3,4- oxadiazoles.This method is using benzoyl hydrazine as reaction raw materials, with DMF(N, dinethylformamide) it is used as carbon source through carbon cyclization, a step constructs 2- phenyl -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) it is the method that one step of carbon source constructs 2- phenyl -1,3,4- oxadiazoles.
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 benzoyl hydrazine as reaction raw materials, in mild reaction item
Part constructs 2- phenyl -1,3,4- oxadiazoles in next step.
2- phenyl -1,3 that the present invention synthesizes, 4- oxadiazoles, structural formula are as follows:
。
With DMF(N, dinethylformamide) it is that one step of carbon source constructs 2- phenyl -1,3, the method for 4- oxadiazoles is such
The synthesis of compound provides new synthesis path, because of its simple synthetic line, has huge application value.Specific synthesis
Path is as follows:
。
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 phenyl -1 2-,
The method of 3,4- oxadiazoles.
Specific steps are as follows:
Raw material is weighed according to following molar ratio, catalyst: oxidant: benzoyl hydrazine=0.05 ~ 0.5:1 ~ 4:1；By weighed raw material
It is placed in reaction vessel, is added solvent n,N-Dimethylformamide (DMF), carbon cyclization 1 ~ 72 is carried out at 40 ~ 150 DEG C
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- phenyl -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 is the nuclear magnetic resonance spectroscopy of 2- phenyl -1,3,4- oxadiazoles obtained in the embodiment of the present invention 1.
Fig. 3 is the carbon-13 nmr spectra of 2- phenyl -1,3,4- oxadiazoles obtained in the embodiment of the present invention 1.
Specific embodiment
The invention is further described below by specific embodiment.
Embodiment 1:
0.2 mM of benzoyl hydrazine of the addition in the test tube of 25 mL, 0.05 mM of cuprous iodide, 0.2 mmoles of potassium peroxydisulfate
You, is added DMF(N, dinethylformamide) it is used as solvent, it is stirred at 120 DEG C.TLC(thin-layered chromatography) detection reaction knot
Reaction solution is cooled to room temperature, reaction solution filtering, extraction, filtrate decompression revolving removal solvent after beam, then passes through column chromatography for separation
Purifying, obtains target product 2- phenyl -1,3,4- oxadiazoles, column chromatographic eluate used is the petroleum ether that volume ratio is 3:1:
Ethyl acetate mixtures, yield 68%.
The present embodiment structure of title compound is shown in Fig. 2 and Fig. 3.
Comparative example 1:
0.2 mM of benzoyl hydrazine of the addition in the test tube of 25 mL, 0.05 mM of cuprous iodide, tert-butyl hydroperoxide 0.2
MM, DMF(N, dinethylformamide is added) it is used as solvent, it is stirred at 120 DEG C.TLC(thin-layered chromatography) tracking inspection
It surveys, does not detect target product.
Comparative example 2:
0.2 mM of benzoyl hydrazine of the addition in the test tube of 25 mL, 0.05 mM of cuprous iodide, 0.2 mM of silver carbonate,
DMF(N, dinethylformamide is added) it is used as solvent, it is stirred under 120 degrees Celsius.TLC(thin-layered chromatography) tracing detection,
Do not detect target product.
Comparative example 3:
0.2 mM of benzoyl hydrazine of the addition in the test tube of 25 mL, 0.05 mM of cuprous iodide, 0.2 mM of silver nitrate,
DMF(N, dinethylformamide is added) it is used as solvent, it is stirred under 120 degrees Celsius.TLC(thin-layered chromatography) tracing detection,
Do not detect target product.
Comparative example 4:
0.2 mM of benzoyl hydrazine of the addition in the test tube of 25 mL, 0.05 mM of cuprous iodide, 0.2 mM of silver oxide,
DMF(N, dinethylformamide is added) it is used as solvent, it is stirred under 120 degrees Celsius.TLC(thin-layered chromatography) tracing detection,
Do 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 | 68 |
| 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 benzoyl hydrazine, and raw material is simple and easy to get, the target product 1,3 of generation,
4- oxadiazoles is then the star molecule of drug field, which is that the synthesis of 1,3,4- furodiazole compounds provides newly
Research Thinking.
Claims (1)
1. a kind of construct 2- phenyl -1,3, the method for 4- oxadiazoles, it is characterised in that specific steps by one step of carbon source of DMF are as follows:
Raw material is weighed according to following molar ratio, catalyst: oxidant: benzoyl hydrazine=0.05 ~ 0.5:1 ~ 4:1；By weighed raw material
It is placed in reaction vessel, solvent n,N-Dimethylformamide is added, is carried out carbon cyclization 1 ~ 72 hour at 40 ~ 150 DEG C；
Products therefrom is isolated and purified using column chromatography, and column chromatographic eluate is the mixed liquor of petroleum ether and ethyl acetate, wherein petroleum
The volume ratio of ether and ethyl acetate is 1 ~ 40:1, after isolating and purifying, obtains 2- phenyl -1,3,4- oxadiazoles；
The catalyst is cuprous iodide；
The oxidant is potassium peroxydisulfate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811341557.6A CN109251185A (en) | 2018-11-12 | 2018-11-12 | The method for constructing 2- phenyl -1,3,4- oxadiazoles as one step of carbon source using DMF |
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|---|---|---|---|
| CN201811341557.6A CN109251185A (en) | 2018-11-12 | 2018-11-12 | The method for constructing 2- phenyl -1,3,4- oxadiazoles as one step of carbon source using DMF |
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|---|---|
| CN109251185A true CN109251185A (en) | 2019-01-22 |
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|---|---|---|---|
| CN201811341557.6A Withdrawn CN109251185A (en) | 2018-11-12 | 2018-11-12 | The method for constructing 2- phenyl -1,3,4- oxadiazoles as one step of carbon source using DMF |
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2018
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Application publication date: 20190122 |
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