CN109206418A - Using DMF as one step of carbon source construct 2-(2- furyl) -1,3,4- oxadiazoles method - Google Patents
Using DMF as one step of carbon source construct 2-(2- furyl) -1,3,4- oxadiazoles method Download PDFInfo
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- CN109206418A CN109206418A CN201811342122.3A CN201811342122A CN109206418A CN 109206418 A CN109206418 A CN 109206418A CN 201811342122 A CN201811342122 A CN 201811342122A CN 109206418 A CN109206418 A CN 109206418A
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- furyl
- oxadiazoles
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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Abstract
The invention discloses one kind with DMF(N, dinethylformamide) be one step of carbon source construct 2-(2- furyl) -1,3,4- oxadiazoles method.This method is using 2- furoyl hydrazine as reaction raw materials, with DMF(N, dinethylformamide) it is used as carbon source through carbon cyclization, a step constructs 2-(2- furyl) -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-(2- furyl) -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 2- furoyl hydrazine as reaction raw materials, mild anti-
Condition is answered to construct 2-(2- furyl in next step) -1,3,4- oxadiazoles.
The 2-(2- furyl 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-(2- furyl) -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-(2- furans
Base) -1,3,4- oxadiazoles method.
Specific steps are as follows:
Raw material is weighed according to following molar ratio, catalyst: oxidant: 2- furoyl hydrazine=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-(2- furyl) -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-(2- furyl) -1,3,4- oxadiazoles nuclear magnetic resonance spectroscopy.
Fig. 3 be the embodiment of the present invention 1 obtained in 2-(2- furyl) -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 2- furoyl hydrazine 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-(2- furyl 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 40%.
The present embodiment structure of title compound is shown in Fig. 2 and Fig. 3.
Comparative example 1:
0.2 mM of the 2- furoyl hydrazine of 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 the 2- furoyl hydrazine of 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 the 2- furoyl hydrazine of 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 the 2- furoyl hydrazine of 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 | 40 |
| 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 2- furoyl hydrazine, 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-(2- furyl 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: 2- furoyl 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-(2- furyl) -1,3,4- oxadiazoles；
The catalyst is cuprous iodide；
The oxidant is potassium peroxydisulfate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811342122.3A CN109206418A (en) | 2018-11-12 | 2018-11-12 | Using DMF as one step of carbon source construct 2-(2- furyl) -1,3,4- oxadiazoles method |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811342122.3A CN109206418A (en) | 2018-11-12 | 2018-11-12 | Using DMF as one step of carbon source construct 2-(2- furyl) -1,3,4- oxadiazoles method |
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| Publication Number | Publication Date |
|---|---|
| CN109206418A true CN109206418A (en) | 2019-01-15 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201811342122.3A Withdrawn CN109206418A (en) | 2018-11-12 | 2018-11-12 | Using DMF as one step of carbon source construct 2-(2- furyl) -1,3,4- oxadiazoles method |
Country Status (1)
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| CN (1) | CN109206418A (en) |
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2018
- 2018-11-12 CN CN201811342122.3A patent/CN109206418A/en not_active Withdrawn
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