CN105085420A - Method for catalytically synthesizing phenazine compounds in water phase under microwave radiation - Google Patents
Method for catalytically synthesizing phenazine compounds in water phase under microwave radiation Download PDFInfo
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- CN105085420A CN105085420A CN201510570399.1A CN201510570399A CN105085420A CN 105085420 A CN105085420 A CN 105085420A CN 201510570399 A CN201510570399 A CN 201510570399A CN 105085420 A CN105085420 A CN 105085420A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/46—Phenazines
Abstract
The invention discloses a method for catalytically synthesizing phenazine compounds in a water phase under microwave radiation, which comprises the following steps: adding a catalytic amount of catalyst ferric chloride or nickelous chloride, a cocatalyst lithium proline, a substrate substituted 2-haloaniline, a phase-transfer catalyst 4-butyl ammonium chloride, 4-butyl ammonium bisulfate or 4-butyl ammonium bromide, an inorganic alkali or organic alkali and water into a reaction vessel, putting into a microwave reaction instrument, reacting at certain temperature under certain power for some time, concentrating under reduced pressure, and purifying the product by column chromatography. The method for preparing phenazine compounds is friendly to the environment, simple to operate and high in efficiency. Compared with the prior art, the method has the advantages of obviously higher reaction speed than conventional heating, mild reaction conditions, high yield, high safety, low cost and environment friendliness, and is simple to operate.
Description
Technical field
The present invention relates to method prepared by phenazene derivative.Namely adopt replacement 2-halogen aromatic amines to be raw material, introduce microwave as auxiliary synthesizing mean, efficient catalytic prepares the method for compound phenazine fast.
Background technology
Azophenlyene, as a class of nitrogenous fused heterocyclic compound, has certain special status in organic chemistry filed, and it is that the mankind are first with a kind of material that can dye that chemical method obtains.Afterwards, it is found that azophenlyene had biological activity, can sterilant be used as.The application of azophenlyene is in recent years more and more extensive, as being applied to the field such as antitumor drug, antibacterial, molecular light switch, solar energy converting and macromolecular material, more and more causes the attention of people at present at medicine, the energy and Material Field.
The synthesis compound phenazine method of bibliographical information mainly contains following several: (1) with oil of mirbane and aniline for raw material, under highly basic existent condition, synthesis azophenlyene.(2) with 2-aminodiphenylamine for raw material, calcium oxide is as catalyzer, and under nitrogen protection, 600 DEG C of pyroreaction 40min generate.(3) with adjacent amino-diphenyl-amine for raw material, under the effect of plumbous oxide, generate adjacent nitrodiphenylamine, then under the catalysis of 0 valency metal or metal suboxide, ring-closure reaction occur, can target compound be obtained.(4) by tea phenol and adjacent two amidos under a certain pressure, be heated to 200-210 DEG C, reaction 35-40h, prepares intermediate 5,10-dihydrophenazine, then is converted to azophenlyene.The synthetic method of the compound phenazine of current report respectively has relative merits, and more or less because raw material acquisition is difficult, portion of reagent is poisoned greatly, reaction conditions is violent and environmental pollution serious, use is restricted.Therefore, seeking azophenlyene synthetic method that is easy, efficient, environmental protection is its urgent problem in application process.
Over nearly 20 years, copper catalysis Ullmann reaction achieves significant achievement, and its strategy has been applied in fused ring compound synthesis.Synthesis copper catalysis being expanded to azophenlyene will make full use of the advantage of the reaction conditions gentleness of metal catalyst.From Gedye in 1986 first by microwave technique application after organic synthesis, the application of microwave technology in organic reaction is increasingly extensive.With traditional heating reacting phase ratio, the organic synthesis under microwave radiation has that speed is fast, productive rate is high, principle utilization ratio advantages of higher, realizes Atom economy synthesis.
The method of synthesis phenazene derivative is disclosed in the present invention.Namely adopt replacement 2-halogen aromatic amines to be raw material, introduce microwave as auxiliary synthesizing mean, prepared the method for compound phenazine by efficient catalytic fast.Compared with method described in prior art, this system speed of response is comparatively obviously accelerated under conventional heating, and reaction conditions is gentle, simple to operate, productive rate is high, safety, with low cost, environmental protection.
Summary of the invention
The object of this invention is to provide a kind of method catalyzing and synthesizing compound phenazine in aqueous phase under microwave radiation, is the method that catalyst replaces 2-halo aniline synthesis compound phenazine under pure water mutually middle microwave radiation in more detail.
The technical scheme realizing the object of the invention is as follows: a kind of described method catalyzing and synthesizing phenazene derivative in aqueous phase under microwave radiation, as chemical equation (A), its concrete steps are as follows: in reaction vessel, add catalytic amount catalyzer iron(ic) chloride or nickelous chloride, cocatalyst proline(Pro) lithium and replacement 2-halo aniline substrate, phase-transfer catalyst 4-butyl ammonium chloride, 4-butyl monoammonium sulfate or 4-butyl brometo de amonio, mineral alkali or organic bases and water, be placed in microwave reaction instrument to react under certain temperature and power, after certain hour, concentrating under reduced pressure, product is through column chromatography purification,
（A）
Wherein R be H or be selected from 4 replace containing C
1-4low alkyl group, nitro, Cl, F, ethanoyl, hydroxyl, methoxyl group or itrile group; X is Br, I.
In above-mentioned concrete steps, the usage quantity of catalyzer is 0.01-0.5 times that replaces 2-halogen aromatic amines weight.
In above-mentioned concrete steps, the usage quantity of cocatalyst proline(Pro) lithium is 0.01-0.5 times that replaces 2-halogen aromatic amines weight.
Mineral alkali described in above-mentioned concrete steps is sodium hydroxide, cesium carbonate, sodium carbonate, potassium hydroxide or potassiumphosphate; Described organic bases is selected from triethylamine, tripropyl amine, Tributylamine or diisopropylethylamine.
In above-mentioned concrete steps, the mole dosage of mineral alkali is 1-10 times with the replacement 2-halogen aromatic amines of R group.
In above-mentioned concrete steps, the consumption of phase-transfer catalyst 4-butyl ammonium chloride, 4-butyl monoammonium sulfate or 4-butyl brometo de amonio is 0.1-10 times with the replacement 2-halogen aromatic amines weight of R group.
The concentration of the replacement 2-halogen aromatic amines with R group in above-mentioned concrete steps is 0.1-0.9mol/L.
Temperature of reaction in above-mentioned concrete steps in microwave reaction instrument is 20-200 DEG C.
Reaction times in above-mentioned concrete steps in microwave reaction instrument is 10-60min.
Power in above-mentioned concrete steps in microwave reaction instrument is 10-200W.
Specifically, the present invention replaces 2-halo aniline for raw material with reaction substrate, and under the effect of catalyzer, phase-transfer catalyst and alkali, microwave-assisted reaction forms, and reaction formula is as follows:
Described catalyzer is FeCl
3/ proline(Pro) lithium or NiCl
2/ proline(Pro) lithium, preferred FeCl
3/ proline(Pro) lithium, wherein FeCl
3, NiCl
2for catalyzer, proline(Pro) lithium is cocatalyst.
Described reaction PTC is phase-transfer catalyst, can be 4-butyl ammonium chloride, 4-butyl monoammonium sulfate, 4-butyl brometo de amonio etc., preferred 4-butyl brometo de amonio.
According to the present invention, substrate (I), for replacing 2-halo aniline, can synthesize phenazene derivative in this water react system;
(I)。
Above formula (I) wherein R be H or 4 replace containing C
1-4low alkyl group, nitro, Cl, F, ethanoyl, hydroxyl, methoxyl group, itrile group; X is halogen atom Br, I.
Products therefrom (II), wherein R be H or 4 replace containing C
1-4low alkyl group, nitro, Cl, F, ethanoyl, hydroxyl, methoxyl group, itrile group;
（Ⅱ）。
Reaction system is implemented under mineral alkali or organic bases exist, preferred mineral alkali.Mineral alkali can be potassium hydroxide, lithium hydroxide, sodium hydroxide, cesium carbonate, Potassium monofluoride, salt of wormwood, sodium carbonate, potassiumphosphate, sodium bicarbonate, dipotassium hydrogen phosphate, saleratus, sodium acetate, potassium acetate, Sodium propanecarboxylate, sodium methylate, sodium ethylate, sodium tert-butoxide, potassium tert.-butoxide, trimethylacetic acid sodium, and organic bases can be triethylamine, tripropyl amine, Tributylamine, diisopropylethylamine.Preferred use sodium hydroxide, cesium carbonate, sodium carbonate, potassium hydroxide, potassiumphosphate.
Replacing 2-halo aniline (I) based on 1mol is standard, and the consumption of described alkali is 1 to 10mol, is preferably 2 to 5mol, is more preferably 4mol.
In preferred version of the present invention, replacing 2-halo aniline (I) based on 1mol is standard, and the usage quantity of catalyzer is 0.01mol to 0.5mol, and preferred 0.1mol to 0.4mol, is more preferably 0.05 to 0.3mol.
In preferred version of the present invention, replacing 2-halo aniline (I) based on 1mol is standard, and the usage quantity of cocatalyst is 0.01mol to 0.5mol, and preferred 0.1mol to 0.4mol, is more preferably 0.05 to 0.3mol.
In preferred version of the present invention, phase-transfer catalyst can be 4-butyl ammonium chloride, 4-butyl monoammonium sulfate, 4-butyl brometo de amonio etc., more preferably 4-butyl brometo de amonio.
In preferred version of the present invention, replacing 2-halo aniline (I) based on 1mol is standard, and the usage quantity of phase-transfer catalyst is 0.1mol to 10mol, and preferred 0.1mol to 0.5mol, is more preferably 0.1mol.
Consumption as the water of solvent can change in wide scope.The concentration of reaction substrate (replacing 2-halo puratized agricultural spray) is preferably 0.1 to 0.9mol/L, is more preferably 0.3 to 0.4mol/L.
In microwave reaction instrument, temperature of reaction is 20 DEG C-200 DEG C, preferably implements under the condition of 60 DEG C-150 DEG C.
In microwave reaction instrument, the reaction times is 10min-60min, preferred 20min-40min.
In microwave reaction instrument, microwave power is 10W-200W, preferred 100W-200W.
Advantage of the present invention is: the present invention is a kind of environmental friendliness, easy and simple to handle, and safety is cheap, prepares the method for compound phenazine efficiently.Compared with prior art, this method speed of response is comparatively obviously accelerated under conventional heating, and reaction conditions is gentle, simple to operate, productive rate is high, safety, with low cost, environmental protection.
Embodiment
embodiment 1: azophenlyene:in reaction vessel, add 2-Iodoaniline 1mmol, order adds iron(ic) chloride 0.1mmol, proline(Pro) lithium 0.1mmol (prolinelithiumas), sodium hydroxide 3mmol, 4-butyl brometo de amonio ((
nbu)
4nBr) 0.1mmol, water 3mL.Be placed in microwave reaction instrument under 150W power, be heated to 100 DEG C of successive reaction 30min.Be cooled to room temperature, concentrating under reduced pressure after reaction terminates, product, through column chromatography purification, obtains yellow solid, productive rate 79%.
embodiment 2:2,7-dimethylphenazine:in reaction vessel, add 2-iodo-4-monomethylaniline 1mmol, order adds iron(ic) chloride 0.1mmol, proline(Pro) lithium 0.1mmol (prolinelithiumas), sodium hydroxide 3mmol, 4-butyl brometo de amonio ((
nbu)
4nBr) 0.1mmol, water 3mL.Be placed in microwave reaction instrument under 150W power, be heated to 100 DEG C of successive reaction 30min.Be cooled to room temperature, concentrating under reduced pressure after reaction terminates, product, through column chromatography purification, obtains yellow solid, productive rate 84%.
embodiment 3:2,7-diethyl azophenlyene:preparation method, with embodiment 2, adds the iodo-4-ethylaniline 1mmol of 2-, obtains yellow solid, productive rate 86%.
embodiment 4:2,7-dipropyl azophenlyene:preparation method, with embodiment 2, adds 2-iodo-4-propyl group aniline 1mmol, obtains yellow solid, productive rate 86%.
embodiment 5:2,7-dibutyl azophenlyene:preparation method, with embodiment 2, adds 2-iodo-4-butylaniline 1mmol, obtains yellow solid, productive rate 88%.
embodiment 6:2,7-diacetyl azophenlyene:preparation method, with embodiment 2, adds 2-iodo-4-ethanoyl aniline 1mmol, obtains yellow solid, productive rate 72%.
embodiment 7:2,7-dinitrobenzene azophenlyene:preparation method, with embodiment 2, adds 2-iodo-4-N-methyl-p-nitroaniline 1mmol, obtains yellow solid, productive rate 66%.
embodiment 8:2,7-bis-chloracizin:preparation method, with embodiment 2, adds 2-iodo-4-chloroaniline 1mmol, obtains yellow solid, productive rate 51%.
embodiment 9:2,7-bis-fluphenazine:preparation method, with embodiment 2, adds 2-iodo-4-fluoroaniline 1mmol, obtains yellow liquid, productive rate 47%.
embodiment 10:2,7-dihydroxyphenazine:preparation method, with embodiment 2, adds 2-iodo-4-hydroxyanilines 1mmol, obtains yellow solid, productive rate 85%.
embodiment 11:2,7-dimethoxy azophenlyene:preparation method, with embodiment 2, adds 2-iodo-4-anisidine 1mmol, obtains yellow solid, productive rate 81%.
embodiment 12:2,7-dinitrile azophenlyene:preparation method, with embodiment 2, adds 2-iodo-4-itrile group aniline 1mmol, obtains yellow solid, productive rate 62%.
embodiment 13: azophenlyene:in reaction vessel, add 2-bromaniline 1mmol, order adds iron(ic) chloride 0.1mmol, proline(Pro) lithium 0.1mmol (prolinelithiumas), sodium hydroxide 3mmol, 4-butyl brometo de amonio ((
nbu)
4nBr) 0.1mmol, water 3mL.Be placed in microwave reaction instrument under 150W power, be heated to 100 DEG C of successive reaction 30min.Be cooled to room temperature, concentrating under reduced pressure after reaction terminates, product, through column chromatography purification, obtains yellow solid, productive rate 71%.
embodiment 14:2,7-dimethylphenazine:in reaction vessel, add 2-bromo-4-monomethylaniline 1mmol, order adds iron(ic) chloride 0.1mmol, proline(Pro) lithium 0.1mmol (prolinelithiumas), sodium hydroxide 3mmol, 4-butyl brometo de amonio ((
nbu)
4nBr) 0.1mmol, water 3mL.Be placed in microwave reaction instrument under 150W power, be heated to 100 DEG C of successive reaction 30min.Be cooled to room temperature, concentrating under reduced pressure after reaction terminates, product, through column chromatography purification, obtains yellow solid, productive rate 75%.
embodiment 15:2,7-diethyl azophenlyene:preparation method, with embodiment 14, adds the bromo-4-ethylaniline 1mmol of 2-, obtains yellow solid, productive rate 76%.
embodiment 16:2,7-dipropyl azophenlyene:preparation method, with embodiment 14, adds 2-bromo-4-propyl group aniline 1mmol, obtains yellow solid, productive rate 78%.
embodiment 17:2,7-dibutyl azophenlyene:preparation method, with embodiment 14, adds 2-bromo-4-butylaniline 1mmol, obtains yellow solid, productive rate 78%.
embodiment 18:2,7-diacetyl azophenlyene:preparation method, with embodiment 14, adds 2-bromo-4-ethanoyl aniline 1mmol, obtains yellow solid, productive rate 61%.
embodiment 19:2,7-dinitrobenzene azophenlyene:preparation method, with embodiment 14, adds 2-bromo-4-N-methyl-p-nitroaniline 1mmol, obtains yellow solid, productive rate 66%.
embodiment 20:2,7-bis-chloracizin:preparation method, with embodiment 14, adds 2-bromo-4-chloroaniline 1mmol, obtains yellow solid, productive rate 42%.
embodiment 21:2,7-bis-fluphenazine:preparation method, with embodiment 14, adds 2-bromo-4-fluoroaniline 1mmol, obtains yellow liquid, productive rate 37%.
embodiment 22:2,7-dihydroxyphenazine:preparation method, with embodiment 14, adds 2-bromo-4-hydroxyanilines 1mmol, obtains yellow solid, productive rate 75%.
embodiment 23:2,7-dimethoxy azophenlyene:preparation method, with embodiment 14, adds 2-bromo-4-anisidine 1mmol, obtains yellow solid, productive rate 71%.
embodiment 24:2,7-dinitrile azophenlyene:preparation method, with embodiment 14, adds 2-bromo-4-itrile group aniline 1mmol, obtains yellow solid, productive rate 53%.
embodiment 25: azophenlyene:in reaction vessel, add 2-Iodoaniline 1mmol, order adds nickelous chloride 0.1mmol, proline(Pro) lithium 0.1mmol (prolinelithiumas), sodium hydroxide 3mmol, 4-butyl brometo de amonio ((
nbu)
4nBr) 0.1mmol, water 3mL.Be placed in microwave reaction instrument under 150w power, be heated to 100 DEG C of successive reaction 30min.Be cooled to room temperature, concentrating under reduced pressure after reaction terminates, product, through column chromatography purification, obtains yellow solid, productive rate 45%.
embodiment 26: azophenlyene:in reaction vessel, add 2-bromaniline 1mmol, order adds nickelous chloride 0.1mmol, proline(Pro) lithium 0.1mmol (prolinelithiumas), sodium hydroxide 3mmol, 4-butyl brometo de amonio ((
nbu)
4nBr) 0.1mmol, water 3mL.Be placed in microwave reaction instrument under 150W power, be heated to 100 DEG C of successive reaction 30min.Be cooled to room temperature, concentrating under reduced pressure after reaction terminates, product, through column chromatography purification, obtains yellow solid, productive rate 35%.
The foregoing is only preferred embodiment of the present invention, not in order to limit the present invention, all any amendments done within the spirit and principles in the present invention, equivalent replacement and improvement etc., all should be included within protection scope of the present invention.
Claims (10)
1. one kind catalyzes and synthesizes the method for phenazene derivative in aqueous phase under microwave radiation, as chemical equation (A), its concrete steps are as follows: in reaction vessel, add catalyzer iron(ic) chloride or nickelous chloride, the cocatalyst proline(Pro) lithium of catalytic amount and replace 2-halo aniline substrate, phase-transfer catalyst 4-butyl ammonium chloride, 4-butyl monoammonium sulfate or 4-butyl brometo de amonio, mineral alkali or organic bases and water, be placed in microwave reaction instrument to react under certain temperature and power, after certain hour, concentrating under reduced pressure, product is through column chromatography purification;
（A）
Wherein R be H or be selected from 4 replace containing C
1-4low alkyl group, nitro, Cl, F, ethanoyl, hydroxyl, methoxyl group or itrile group; X is Br, I.
2. method according to claim 1, is characterized in that the usage quantity of catalyzer in concrete steps is 0.01-0.5 times that replaces 2-halogen aromatic amines weight.
3. method according to claim 1, is characterized in that the usage quantity of cocatalyst proline(Pro) lithium in concrete steps is 0.01-0.5 times that replaces 2-halogen aromatic amines weight.
4. method according to claim 1, is characterized in that mineral alkali described in concrete steps is sodium hydroxide, cesium carbonate, sodium carbonate, potassium hydroxide or potassiumphosphate; Described organic bases is selected from triethylamine, tripropyl amine, Tributylamine or diisopropylethylamine.
5. the method according to claim 1 or 4, is characterized in that the mole dosage of mineral alkali in concrete steps is 1-10 times with the replacement 2-halogen aromatic amines of R group.
6. the method according to claim 1 or 2 or 3, is characterized in that the consumption of phase-transfer catalyst 4-butyl ammonium chloride, 4-butyl monoammonium sulfate or 4-butyl brometo de amonio in concrete steps is 0.1-10 times with the replacement 2-halogen aromatic amines weight of R group.
7. the method according to claim 1 or 2 or 3, is characterized in that the concentration of the replacement 2-halogen aromatic amines with R group in concrete steps is 0.1-0.9mol/L.
8. method according to claim 1, is characterized in that the temperature of reaction in concrete steps in microwave reaction instrument is 20-200 DEG C.
9. method according to claim 1, is characterized in that the reaction times in concrete steps in microwave reaction instrument is 10-60min.
10. method according to claim 1, is characterized in that the power in concrete steps in microwave reaction instrument is 10-200W.
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| CN106866543A (en) * | 2017-04-16 | 2017-06-20 | 福建医科大学 | A kind of method for catalyzing and synthesizing benzimidazole compound under microwave in water phase |
| CN113121458A (en) * | 2021-04-16 | 2021-07-16 | 河南科技大学 | Method for rapidly synthesizing 2, 3-diaminophenazine by ultrasonic radiation catalysis |
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| CN105837521A (en) * | 2016-05-03 | 2016-08-10 | 苏州大学 | 2, 7- dibromo-1, 3, 4, 6, 8, 9-hexafluorophenazine and crystal form and preparation method thereof |
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| CN106866543B (en) * | 2017-04-16 | 2019-05-14 | 福建医科大学 | A method of benzimidazole compound is catalyzed and synthesized under microwave radiation in water phase |
| CN113121458A (en) * | 2021-04-16 | 2021-07-16 | 河南科技大学 | Method for rapidly synthesizing 2, 3-diaminophenazine by ultrasonic radiation catalysis |
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