CN108084109A - Synthesis method of 2, 5-disubstituted-1, 3, 4-oxadiazole - Google Patents

Synthesis method of 2, 5-disubstituted-1, 3, 4-oxadiazole Download PDF

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Publication number
CN108084109A
CN108084109A CN201711440986.4A CN201711440986A CN108084109A CN 108084109 A CN108084109 A CN 108084109A CN 201711440986 A CN201711440986 A CN 201711440986A CN 108084109 A CN108084109 A CN 108084109A
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reaction
eosiny
synthesis
potassium carbonate
catalyst
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郭成
戈言芹
孙俊
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Nanjing Tech University
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Nanjing Tech University
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D271/00Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/101,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D409/00Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings

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  • 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 a synthetic method of a drug intermediate 2, 5-disubstituted-1, 3, 4-oxadiazole. The invention takes simple hydrazide compounds as raw materials to synthesize the 2, 5-disubstituted-1, 3, 4-oxadiazole by a one-pot method under the photocatalysis. The common halogen lamp is used as a light source, eosinY is used as a catalyst, potassium carbonate is used as an additive, ethanol is used as a solvent, and the reaction can be carried out at room temperature to generate the 2, 5-disubstituted-1, 3, 4-oxadiazole. The invention has the characteristics of simple raw material source, mild reaction condition and the like.

Description

One kind 2,5- bis- substitutes the synthetic method of -1.3.4- oxadiazoles
Technical field
The invention belongs to symmetrical 2,5- bis- to substitute -1.3.4- oxadiazoles and its derivative preparing technical field.It is specifically related to One kind is in ethanol solution, using potassium carbonate as alkali, dye class catalyst eosin Y catalysis hydrazide kind compounds generation symmetrical 2, 5- bis- substitutes the method for -1.3.4- oxadiazoles and its derivative.
Background technology
Heterocycle 1.3.4- oxadiazoles are a kind of very big reactive intermediates of application value of field of fine chemical, in many drugs It can be found in the molecular structure of chemistry.
EosinY belongs to dye class catalyst, and due to it efficiently, inexpensively, it is a large amount of that the features such as dosage is few causes catalytic field Research boom.
Many synthesis 2,5- bis- disclosed in recent years substitute the method for -1.3.4- oxadiazoles.Mainly make multi-component anti- More complicated raw material should or be used, what is had will use transition-metal catalysis, and the reaction time is longer, and condition is harsh. Catalyst is made using common eosinY in this article, realize under room temperature and air conditions can catalytic reaction carry out, have Easy to operate, mild condition is swift in response, high conversion rate and the advantages that high income.
The content of the invention
It is an object of the invention to provide a kind of operating condition is simple, reaction condition is mild, high selectivity, the system of high income The method of standby cinnamic acid ester derivant.Compared with the method in the prior art, this system maximum feature is to use catalytic amount Catalyst, easy to operate, raw material is easy to get, it is small to pollute, safety is cheap and environmentally protective.
For the present invention using common dyestuff catalyst eosinY as catalyst, hydrazide kind compound is reaction substrate, reaction temperature Spend for room temperature, the reaction time for 12 it is small when or so, efficient catalytic prepares symmetrical 2,5- bis- and substitutes -1.3.4- Evil in ethyl alcohol phase Diazole and its derivative.Wherein, hydrazide kind compound used include to methyl, to methoxyl group, to tertiary butyl, to chlorine, to bromine Benzoyl hydrazine and heterocyclic thiophene hydrazides.
The specific reaction equation such as chemical equation (1) of the present invention:
Wherein R is (1) containing methyl, methoxyl group, the phenyl ring of the substituent groups such as tertiary butyl, halogen (fluorine, chlorine).
(2) thiophene heterocycle.
The preferred reaction step of the present invention is as follows:The benzoyl hydrazine of 0.5mmol is added in the reaction tube of 10ml Then the potassium carbonate 0.138g of photochemical catalyst the eosinY 0.010g and 1mmol of 0.068g, 3mol% add in 2ml solvents, use Light intensity 0.4W/cm2Reaction is stirred at room temperature with fan control in halogen light irradiation.React 12 it is small when after, in reaction solution use column chromatography Methods For Purification product.
The catalyst eosinY dosages can be 2mol%, 3mol%, 5mol%.
The additive basic can be potassium carbonate (K2CO3), potassium phosphate (K3PO4), sodium phosphate (Na3PO4), triethylamine (Et3N)。
Solvent used has ethyl alcohol, methanol, isopropanol, tetrahydrofuran in this reaction, and wherein ethyl alcohol effect is best.
The present invention relates to compound it is specific as follows:
The present invention has the following advantages:In the reaction using under single reaction raw material, the catalyst of catalytic amount, illumination condition Room temperature is with regard to that can smoothly complete.
Description of the drawings
The simple main reactant (hydrazide kind compound) for illustrating the reaction of attached drawing 1 and product (2,5- bis- substitute- 1.3.4- oxadiazole).
Attached drawing 2 is shown as the H spectrum spectrograms of compound 1-1.
Specific embodiment
It lifts specific embodiment again below to be further described the present invention, single present disclosure is not limited thereto.
Embodiment 1:Use the preparation of eosinY catalysis 2, the 5- diphenyl -1.3.4- oxadiazoles of 2mol%.
The photochemical catalyst eosinY of the benzoyl hydrazine 0.068g 2mol% of 0.5mmol is added in the reaction tube of 10ml Then the potassium carbonate 0.138g of 0.007g and 1mmol adds in 2ml alcohol solvents, with light intensity 0.4W/cm2Halogen light irradiation is used Reaction is stirred at room temperature in fan control.React 12 it is small when after, in reaction solution use column chromatography Methods For Purification product.Yield is 29%.
Embodiment 2:Use the preparation of eosinY catalysis 2, the 5- diphenyl -1.3.4- oxadiazoles of 3mol%.
The photochemical catalyst eosinY of the benzoyl hydrazine 0.068g, 3mol% of 0.5mmol are added in the reaction tube of 10ml Then the potassium carbonate 0.138g of 0.010g and 1mmol adds in 2ml alcohol solvents, with light intensity 0.4W/cm2Halogen light irradiation is used Reaction is stirred at room temperature in fan control.React 12 it is small when after, in reaction solution use column chromatography Methods For Purification product.Yield is 68%.
Embodiment 3:Use the preparation of eosinY catalysis 2, the 5- diphenyl -1.3.4- oxadiazoles of 5mol%.
The photochemical catalyst eosinY of the benzoyl hydrazine 0.068g, 5mol% of 0.5mmol are added in the reaction tube of 10ml Then the potassium carbonate 0.138g of 0.017g and 1mmol adds in 2ml alcohol solvents, with light intensity 0.4W/cm2Halogen light irradiation is used Reaction is stirred at room temperature in fan control.React 12 it is small when after, in reaction solution use column chromatography Methods For Purification product.Yield is 68%.
Embodiment 4:Potassium phosphate (K3PO4) it is used for the preparation of 2,5- diphenyl -1.3.4- oxadiazoles.
The photochemical catalyst eosinY of the benzoyl hydrazine 0.068g, 3mol% of 0.5mmol are added in the reaction tube of 10ml Then the potassium phosphate 0.212g of 0.010g and 1mmol adds in 2ml alcohol solvents, with light intensity 0.4W/cm2Halogen light irradiation is used Reaction is stirred at room temperature in fan control.React 12 it is small when after, in reaction solution use column chromatography Methods For Purification product.Yield is 42%.
Embodiment 5:Sodium phosphate (Na3PO4) it is used for the preparation of 2,5- diphenyl -1.3.4- oxadiazoles.
The photochemical catalyst eosinY of the benzoyl hydrazine 0.068g, 3mol% of 0.5mmol are added in the reaction tube of 10ml Then the sodium phosphate 0.164g of 0.010g and 1mmol adds in 2ml alcohol solvents, with light intensity 0.4W/cm2Halogen light irradiation is used Reaction is stirred at room temperature in fan control.React 12 it is small when after, in reaction solution use column chromatography Methods For Purification product.Yield is 39%.
Embodiment 6:Triethylamine (Et3N) it is used for the preparation of 2,5- diphenyl -1.3.4- oxadiazoles.
The photochemical catalyst eosinY of the benzoyl hydrazine 0.068g, 3mol% of 0.5mmol are added in the reaction tube of 10ml Then the triethylamine 0.101g of 0.010g and 1mmol adds in 2ml alcohol solvents, with light intensity 0.4W/cm2Halogen light irradiation is used Reaction is stirred at room temperature in fan control.React 12 it is small when after, in reaction solution use column chromatography Methods For Purification product.Yield is 29%.
Embodiment 7:Methanol as solvent is used for the preparation of 2,5- diphenyl -1.3.4- oxadiazoles.
The photochemical catalyst eosinY of the benzoyl hydrazine 0.068g, 3mol% of 0.5mmol are added in the reaction tube of 10ml Then the potassium carbonate 0.138g of 0.010g and 1mmol adds in 2ml methanol solvates, with light intensity 0.4W/cm2Halogen light irradiation is used Reaction is stirred at room temperature in fan control.React 12 it is small when after, in reaction solution use column chromatography Methods For Purification product.Yield is 55%.
Embodiment 8:Isopropanol makees preparation of the solvent for 2,5- diphenyl -1.3.4- oxadiazoles.
The photochemical catalyst eosinY of the benzoyl hydrazine 0.068g, 3mol% of 0.5mmol are added in the reaction tube of 10ml Then the potassium carbonate 0.138g of 0.010g and 1mmol adds in 2ml isopropanol solvents, with light intensity 0.4W/cm2Halogen light irradiation, Reaction is stirred at room temperature with fan control.React 12 it is small when after, in reaction solution use column chromatography Methods For Purification product.Yield is 62%.
Embodiment 9:Using the eosinY catalyst of 3mol%, potassium carbonate makees additive, and ethanol as solvent is used for 2,5- Bis (3-methylphenyl) -1,3,4-oxadiazole preparation.
The photochemical catalyst of 3- methyl-benzoyl the hydrazines 0.075g, 3mol% of 0.5mmol are added in the reaction tube of 10ml Then the potassium carbonate 0.138g of eosinY 0.010g and 1mmol add in 2ml alcohol solvents, with light intensity 0.4W/cm2Halogen lamp shines It penetrates, reaction is stirred at room temperature with fan control.React 12 it is small when after, in reaction solution use column chromatography Methods For Purification product.Yield For 53%.
Embodiment 10:The eosinY catalyst of 3mol%, potassium carbonate make additive, and ethanol as solvent is used for 2,5-bis (4-methylphenyl) -1,3,4-oxadiazole preparation.
The photochemical catalyst of 4- methyl-benzoyl the hydrazines 0.075g, 3mol% of 0.5mmol are added in the reaction tube of 10ml Then the potassium carbonate 0.138g of eosinY 0.010g and 1mmol add in 2ml alcohol solvents, with light intensity 0.4W/cm2Halogen lamp shines It penetrates, reaction is stirred at room temperature with fan control.React 12 it is small when after, in reaction solution use column chromatography Methods For Purification product.Yield For 70%.
Embodiment 11:The eosinY catalyst of 3mol%, potassium carbonate make additive, and ethanol as solvent is used for 2,5-bis (4-methoxy-phenyl) -1,3,4-oxadiazole preparation.
The photochemical catalyst of 4- methoxy-benzoyl the hydrazines 0.083g, 3mol% of 0.5mmol are added in the reaction tube of 10ml Then the potassium carbonate 0.138g of eosinY 0.010g and 1mmol add in 2ml alcohol solvents, with light intensity 0.4W/cm2Halogen lamp shines It penetrates, reaction is stirred at room temperature with fan control.React 12 it is small when after, in reaction solution use column chromatography Methods For Purification product.Yield For 65%.
Embodiment 12:The eosinY catalyst of 3mol%, potassium carbonate make additive, and ethanol as solvent is used for 2,5-di (4- Tert-butylphenyl) -1,3,4-oxadiazole preparation.
The photochemical catalyst of 4- tertiary butyls-benzoyl hydrazine 0.089g, 3mol% of 0.5mmol is added in the reaction tube of 10ml Then the potassium carbonate 0.138g of eosinY 0.010g and 1mmol add in 2ml alcohol solvents, with light intensity 0.4W/cm2Halogen lamp shines It penetrates, reaction is stirred at room temperature with fan control.React 12 it is small when after, in reaction solution use column chromatography Methods For Purification product.Yield For 71%.
Embodiment 13:The eosinY catalyst of 3mol%, potassium carbonate make additive, and ethanol as solvent is for the double (4- of 2,5- Chlorphenyl) -1, the preparation of 3,4- oxadiazoles.
The 4- chloro- benzoyl hydrazine 0.085g, the photochemical catalyst eosinY of 3mol% of 0.5mmol is added in the reaction tube of 10ml Then the potassium carbonate 0.138g of 0.010g and 1mmol adds in 2ml alcohol solvents, with light intensity 0.4W/cm2Halogen light irradiation, uses wind Fan control room temperature is stirred to react.React 12 it is small when after, in reaction solution use column chromatography Methods For Purification product.Yield is 59%.
Embodiment 14:The eosinY catalyst of 3mol%, potassium carbonate make additive, and ethanol as solvent is for the double (4- of 2,5- Bromophenyl) -1, the preparation of 3,4- oxadiazoles.
The 4- bromo- benzoyl hydrazine 0.107g, the photochemical catalyst eosinY of 3mol% of 0.5mmol is added in the reaction tube of 10ml Then the potassium carbonate 0.138g of 0.010g and 1mmol adds in 2ml alcohol solvents, with light intensity 0.4W/cm2Halogen light irradiation, uses wind Fan control room temperature is stirred to react.React 12 it is small when after, in reaction solution use column chromatography Methods For Purification product.Yield is 56%.
Embodiment 15:The eosinY catalyst of 3mol%, potassium carbonate make additive, and ethanol as solvent is used for 2,5- Dithiophenes The preparation of base -1.3.4- oxadiazoles.
The photochemical catalyst eosinY of 2- thenoyl the hydrazines 0.071g, 3mol% of 0.5mmol are added in the reaction tube of 10ml Then the potassium carbonate 0.138g of 0.010g and 1mmol adds in 2ml alcohol solvents, with light intensity 0.4W/cm2Halogen light irradiation, uses wind Fan control room temperature is stirred to react.React 12 it is small when after, in reaction solution use column chromatography Methods For Purification product.Yield is 60%.

Claims (7)

1. the invention discloses a kind of novel synthesis of common medicine intermediate, using simple hydrazide kind compound as raw material, The one pot process 2 under photocatalysis, 5- bis- substitute -1.3.4- oxadiazoles.Wherein using common halogen lamp as light source, EosinY is catalyst, and potassium carbonate is additive, and ethyl alcohol is solvent, and reaction at room temperature can react generation 2,5- bis- substitutes- 1.3.4- oxadiazole.The invention has the features such as raw material sources are simple, and reaction condition is mild.Target compound general formula below figure:
2. in claim 1, R can be following several:Phenyl ring, thiphene ring containing substituent group etc..
3. in claim 1, in the synthesis of target product, light source is with common halogen lamp (0.4W/cm2).
4. in claim 1, in the synthesis of target product, eosin Y are required catalyst.
5. in claim 1, solvent described in the synthesis of target product is protic:Ethyl alcohol;Methanol;Isopropanol etc., In it is optimal with ethyl alcohol.
6. in claim 1, in the synthesis of target product, potassium carbonate is required additive.
7. in claim 1, in the synthesis of target product, reaction temperature, room temperature.
CN201711440986.4A 2017-12-21 2017-12-21 Synthesis method of 2, 5-disubstituted-1, 3, 4-oxadiazole Pending CN108084109A (en)

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CN109879865A (en) * 2019-03-08 2019-06-14 烟台大学 A kind of preparation method of 2- aryl -5- (2- quinolyl) -1,3,4- furodiazole compound
CN111423394A (en) * 2020-04-28 2020-07-17 常州大学 Synthesis method of 1,3, 4-oxadiazole heterocyclic compound

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109879865A (en) * 2019-03-08 2019-06-14 烟台大学 A kind of preparation method of 2- aryl -5- (2- quinolyl) -1,3,4- furodiazole compound
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CN111423394A (en) * 2020-04-28 2020-07-17 常州大学 Synthesis method of 1,3, 4-oxadiazole heterocyclic compound
CN111423394B (en) * 2020-04-28 2021-11-23 常州大学 Synthesis method of 1,3, 4-oxadiazole heterocyclic compound

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