CN105566235A - Method for synthesizing NH-1,2,3-triazole in steps by utilizing catalysis of aluminium salt - Google Patents
Method for synthesizing NH-1,2,3-triazole in steps by utilizing catalysis of aluminium salt Download PDFInfo
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- CN105566235A CN105566235A CN201610120763.9A CN201610120763A CN105566235A CN 105566235 A CN105566235 A CN 105566235A CN 201610120763 A CN201610120763 A CN 201610120763A CN 105566235 A CN105566235 A CN 105566235A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
- C07D249/06—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles with aryl radicals directly attached to ring atoms
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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Abstract
The invention relates to a method for synthesizing NH-1,2,3-triazole in steps by utilizing the catalysis of aluminium salt, and belongs to the technical field of organic and pharmaceutical synthesis. The method is characterized in that under the catalysis of an aluminium salt catalyst, nitroolefin and sodium azide react in a 1,3-dipolar cycloaddition reaction, wherein the nitroolefin is aryl or aryl-substituted nitroolefin. The method has the following beneficial effects: the method adopts cheap and easily obtained AlCl3, Al2O3 or Al2(SO4)3 as a catalyst; aluminium ions activate nitryl of the nitroolefin, which enables the reaction to be conducted more easily under mild conditions, the yield of the reaction is improved, and an NH-1,2,3-triazole compound is conveniently and efficiently synthesized; compared with the existing methods, the method provided by the invention has the advantages of mild reaction conditions, short reaction time, good safety, convenient operation, high reaction efficiency and low-cost catalyst, and is a method of potential application value.
Description
Technical field
The present invention relates to one and utilize aluminium salt catalysis stepwise synthesis NH-1, the method for 2,3-triazole, belongs to organic and technical field of medicine synthesis.
Technical background
1,2,3-triazole compounds is the nitrogen-containing heterocycle compound that a class has important physiologically active, is widely used in sanitas, agricultural chemicals, optical material, dyestuff, HIV-1 inhibitor, antibiotic, selectivity β 3-class suprarenal gland antagonist, antiviral and anticonvulsive agent.Activity determination shows, 4-aryl-NH-1, and 2,3-triazole compounds can be used as human body methionine aminopeptidase inhibitor.Nearest bibliographical information, some 4-aryl-NH-1,2,3-triazole compounds also has indoleamine 2,3-dioxygenase inhibit activities, potential IDO inhibitor, therefore NH-1,2,3-triazole compounds can as Therapeutic cancer, alzheimer's disease, multiple mankind's major disease such as cataract, wide market.
1,3-dipole Huisgen cycloaddition reaction synthesis of early stage organic azide and Terminal Acetylenes be that Isosorbide-5-Nitrae-two replaces and the mixture of 1,5-bis-substituted triazole.This reaction needed is connected with strong electron-withdrawing group group as activating group on triazo-compound or alkynyl, and needs High Temperature High Pressure and longer reaction times.Therefore, the application of synthesis Isosorbide-5-Nitrae-two replacement-1,2,3-triazoles compound is very limited.
1971, Zefirow etc. reported with NaN
3be raw material with nitroolefin or itrile group alkenes compounds, DMSO is solvent, the method for synthesis 1H-1,2,3-triazole compounds.Although such reaction can be carried out at ambient temperature, alkene containing nitro or itrile group must be used as raw material, and raw material is not easy to obtain, and the versatility of reaction is limited, and productive rate is lower, only has 10% ~ 60%.1994, aryne was added TMSN by Moltzen group
3in, at N
2reflux under protection 72h, through washing remove silica-based after, obtain NH-1,2,3-triazole, yield is 76%.Do not having under Cu (I) catalysis, reaction needed comparatively high temps and for a long time backflow.2004, Kim group reported 2-pyridyl acetylene and TMSN
3reflux in DMF, synthesis 4-(2-pyridyl)-NH-1,2,3-triazole, yield 38% ~ 71%.The method temperature of reaction is higher, and productive rate is not high.In the same year, Yamamoto etc. report alkynes and TMSN under the CuI catalysis of 5mol%
3between cycloaddition reaction.This synthetic method one DMF and MeOH (V:V=9:1) is solvent, and 100 DEG C of reaction 10 ~ 24h, synthesis 4-replacement-NH-1, the yield of 2,3-triazole compounds reaches as high as 95%.The shortcoming of the method is that temperature of reaction is higher, and the time is longer.2006, Barluenga etc. proposed a kind of with (E)-Beta-bromo aromatic ethylene and NaN
3for the effective ways of Material synthesis 1H-1,2,3-triazole compounds, the method is with Pd
2(dba)
3-Xantphos is catalyzer, in Dioxane or DMSO solvent react 14 ~ 24h, almost can be quantitative complete conversion.The shortcoming of the method is to react will use expensive palladium catalyst series, and the reaction times is longer.The same year, Weinreb etc. with one commercial 4-Tolyl-vinyl sulfone for raw material, in the MeOH system under acid catalysis and NaN
3reaction, has synthesized a kind of valuable intermediate β-4-vinyl toluene nitrine (TSE-N
3).This intermediate obtains the 1,2,3-triazoles of TSE-protection by 1,3-Dipolar Cycloaddition of Cu (I)-catalysis.In THF, protecting group can be sloughed with KOBu-t obtain 4-replacement-1H-1,2,3-triazole, yield 61% ~ 93%.The shortcoming of the method is that synthesis step is more, and the reaction times is longer.2007, Cheng group with homemade arylalkyne nitrile for raw material, and NaN
3one group of 4-aryl-5-itrile group-NH-1 has been synthesized in cycloaddition, 2,3-triazole, yield 50% ~ 80%.The shortcoming of the method is the temperature that reaction needed is higher, and the more difficult synthesis of substrate.2008, Shi etc. reported a kind of with nitroolefin, NaN
3-NH-1 is replaced, the new synthesis route of 2,3-triazole with the three components Reactive Synthesis 4,5-bis-that aromatic aldehyde is raw material.Reaction is with L-proline catalysis, and room temperature reaction 8 ~ 10h in DMSO, yield is generally 70% ~ 90%.
In sum, the method for more than synthesizing NH-1,2,3-triazole compounds all generates difficulty, long reaction time, and temperature of reaction is high, productive rate is low, can fit the few or synthesis difficulty of substrate, material toxicity is large or the shortcoming such as poor stability, expensive catalyst.
Summary of the invention
For solving the deficiencies in the prior art, the object of the present invention is to provide a kind of reaction times short, mild condition, security is good, and what productive rate was high utilizes aluminium salt catalysis stepwise synthesis NH-1, the method for 2,3-triazole.
For achieving the above object, the present invention is achieved by the following technical solutions: utilize aluminium salt catalysis stepwise synthesis NH-1,2, the method of 3-triazole, it is characterized in that: under the catalysis of aluminium salt catalyst, there is 1,3-Dipolar Cycloaddition in nitroolefin and sodiumazide, wherein nitroolefin is the nitroolefin of aryl or substituted aryl.
By such scheme, described aluminium salt catalyst is selected from Al
2o
3, Al
2(SO
4)
3or AlCl
3.
By such scheme, described aluminium salt catalyst is AlCl
3.
By such scheme, aluminium salt catalyst mole dosage is 0.05-0.2 times of nitroolefin consumption.
By such scheme, aluminium salt catalyst mole dosage is 0.1 times of nitroolefin consumption.
By such scheme, solvent for use is DMSO, acetonitrile, methyl alcohol, ethanol, toluene, trichloromethane or THF.
By such scheme, solvent for use is DMSO.
By such scheme, react and carry out in the temperature range of 0-110 DEG C.
By such scheme, reaction is carried out at ambient temperature.
By such scheme, the reaction times is 1-1.5 hour.
Concrete reaction formula involved in the present invention is such as formula shown in I:
The invention has the beneficial effects as follows: the present invention adopts AlCl cheap and easy to get
3, Al
2o
3or Al
2(SO
4)
3as catalyzer, aluminum ion has activated the nitro of nitroolefin, reaction is more easily carried out under mild conditions, improve the productive rate of reaction, easily and effectively synthesized NH-1,2,3-triazole compounds, compared with existing method, reaction conditions gentleness of the present invention, reaction times section, security is good, easy and simple to handle, reaction efficiency is high and catalyzer is cheap, is a kind of method with potential using value.
Embodiment
In order to understand the present invention better, illustrate content of the present invention further below in conjunction with embodiment, but content of the present invention is not only confined to the following examples.
Embodiment 1:
4-phenyl-2H-1, the synthesis of 2,3-triazole:
Reaction formula is:
Concrete steps are: in 50mL round-bottomed flask, add 0.33mmol nitrostyrolene, 0.36mmol sodiumazide, 0.03mmolAlCl
3, 2mLDMSO, after at room temperature magnetic agitation reacts 1 hour, be extracted with ethyl acetate reaction solution, organic layer is through saturated common salt water washing, after anhydrous sodium sulfate drying, namely pressure reducing and steaming solvent obtains thick product, and thick product ethyl acetate/petroleum ether=1:5 (V/V) namely obtains desired product for leacheate carries out post separating-purifying, product is white solid, and yield is 94%.
The nucleus magnetic hydrogen spectrum figure result of products obtained therefrom is:
1hNMR (600MHz, DMSO-d
6): δ 8.32 (s, 1H), 7.84 (d, J=7.4Hz, 2H), 7.43 (t, J=7.7Hz, 2H), 7.33 (t, J=7.4Hz, 1H).
Embodiment 2:
4-phenyl-2H-1, the synthesis of 2,3-triazole:
Reaction formula is:
Concrete steps are: in 50mL round-bottomed flask, add 0.33mmol nitrostyrolene, 0.36mmol sodiumazide, 0.03mmolAl
2o
3, 2mLDMSO, after at room temperature magnetic agitation reacts 1 hour, be extracted with ethyl acetate reaction solution, organic layer is through saturated common salt water washing, after anhydrous sodium sulfate drying, namely pressure reducing and steaming solvent obtains thick product, and thick product ethyl acetate/petroleum ether=1:5 (V/V) namely obtains desired product for leacheate carries out post separating-purifying, product is white solid, and yield is 73%.
The nucleus magnetic hydrogen spectrum figure result of products obtained therefrom is:
1hNMR (600MHz, DMSO-d
6): δ 8.32 (s, 1H), 7.84 (d, J=7.4Hz, 2H), 7.43 (t, J=7.7Hz, 2H), 7.33 (t, J=7.4Hz, 1H).
Embodiment 3:
4-phenyl-2H-1, the synthesis of 2,3-triazole:
Reaction formula is:
Concrete steps are: in 50mL round-bottomed flask, add 0.33mmol nitrostyrolene, 0.36mmol sodiumazide, 0.03mmolAl
2(SO
4)
3, 2mLDMSO, after at room temperature magnetic agitation reacts 1 hour, be extracted with ethyl acetate reaction solution, organic layer is through saturated common salt water washing, after anhydrous sodium sulfate drying, namely pressure reducing and steaming solvent obtains thick product, and thick product ethyl acetate/petroleum ether=1:5 (V/V) namely obtains desired product for leacheate carries out post separating-purifying, product is white solid, and yield is 75%.
The nucleus magnetic hydrogen spectrum figure result of products obtained therefrom is:
1hNMR (600MHz, DMSO-d
6): δ 8.32 (s, 1H), 7.84 (d, J=7.4Hz, 2H), 7.43 (t, J=7.7Hz, 2H), 7.33 (t, J=7.4Hz, 1H).
Embodiment 4:
4-p-methylphenyl-2H-1, the synthesis of 2,3-triazole:
Reaction formula is:
Concrete steps are: in 50mL round-bottomed flask, add 0.33mmol nitro p-methylstyrene, 0.36mmol sodiumazide, 0.03mmolAlCl
3, 2mLDMSO, after at room temperature magnetic agitation reacts 1 hour, be extracted with ethyl acetate reaction solution, organic layer is through saturated common salt water washing, after anhydrous sodium sulfate drying, namely pressure reducing and steaming solvent obtains thick product, and thick product ethyl acetate/petroleum ether=1:5 (V/V) namely obtains desired product for leacheate carries out post separating-purifying, product is white solid, and yield is 90%.
The nucleus magnetic hydrogen spectrum figure result of products obtained therefrom is:
1hNMR (600MHz, DMSO-d6): δ 8.25 (s, 1H), 7.72 (d, J=8.1Hz, 2H), 7.24 (d, J=7.9Hz, 2H), 2.31 (s, 3H).
Embodiment 5:
The synthesis of 4-(2,4 dichloro benzene base)-2H-1,2,3-triazole:
Reaction formula is:
Concrete steps are: in 50mL round-bottomed flask, add 0.33mmol nitro 2,4 dichloro benzene base ethene, 0.36mmol sodiumazide, 0.03mmolAlCl
3, 2mLDMSO, after at room temperature magnetic agitation reacts 1 hour, be extracted with ethyl acetate reaction solution, organic layer is through saturated common salt water washing, after anhydrous sodium sulfate drying, namely pressure reducing and steaming solvent obtains thick product, and thick product ethyl acetate/petroleum ether=1:5 (V/V) namely obtains desired product for leacheate carries out post separating-purifying, product is white solid, and yield is 95%.
The nucleus magnetic hydrogen spectrum figure result of products obtained therefrom is:
1hNMR (600MHz, DMSO-d
6): δ 8.38 (s, 1H), 7.94 (d, J=8.4Hz, 1H), 7.72 (d, J=1.8Hz, 1H), 7.51 (q, J=8.4,2.1Hz, 1H).
Embodiment 6:
4-O-Nitrophenylfluorone-2H-1, the synthesis of 2,3-triazole:
Reaction formula is:
Concrete steps are: in 50mL round-bottomed flask, add 0.33mmol nitro O-Nitrophenylfluorone ethene, 0.36mmol sodiumazide, 0.03mmolAlCl
3, 2mLDMSO, after at room temperature magnetic agitation reacts 1 hour, be extracted with ethyl acetate reaction solution, organic layer is through saturated common salt water washing, after anhydrous sodium sulfate drying, namely pressure reducing and steaming solvent obtains thick product, and thick product ethyl acetate/petroleum ether=1:5 (V/V) namely obtains desired product for leacheate carries out post separating-purifying, product is white solid, and yield is 85%.
The nucleus magnetic hydrogen spectrum figure result of products obtained therefrom is:
1hNMR (600MHz, DMSO-d
6): δ 8.24 (s, 1H), 7.89 (s, 1H), 7.81 (d, J=7.2Hz, 1H), 7.76 – 7.68 (m, 1H), 7.64 – 7.54 (m, 1H).
Embodiment 7:
4-o-bromophenyl-2H-1, the synthesis of 2,3-triazole:
Reaction formula is:
Concrete steps are: in 50mL round-bottomed flask, add 0.33mmol nitro o-bromophenyl ethene, 0.36mmol sodiumazide, 0.03mmolAlCl
3, 2mLDMSO, after at room temperature magnetic agitation reacts 1 hour, be extracted with ethyl acetate reaction solution, organic layer is through saturated common salt water washing, after anhydrous sodium sulfate drying, namely pressure reducing and steaming solvent obtains thick product, and thick product ethyl acetate/petroleum ether=1:5 (V/V) namely obtains desired product for leacheate carries out post separating-purifying, product is white solid, and yield is 95%.
The nucleus magnetic hydrogen spectrum figure result of products obtained therefrom is:
1hNMR (600MHz, CDCl
3): δ 8.27 (s, 1H), 7.81 (d, J=6.1Hz, 1H), 7.68 (q, J=8.1,0.9Hz, 1H), 7.39 (m, J=7.6,1.0Hz, 1H), 7.24 (m, J=7.9,1.7Hz, 1H).
Embodiment 8:
4-Chloro-O-Phenyl-2H-1, the synthesis of 2,3-triazole:
Reaction formula is:
Concrete steps are: in 50mL round-bottomed flask, add 0.33mmol nitro Chloro-O-Phenyl ethene, 0.36mmol sodiumazide, 0.03mmolAlCl
3, 2mLDMSO, after at room temperature magnetic agitation reacts 1 hour, be extracted with ethyl acetate reaction solution, organic layer is through saturated common salt water washing, after anhydrous sodium sulfate drying, namely pressure reducing and steaming solvent obtains thick product, and thick product ethyl acetate/petroleum ether=1:5 (V/V) namely obtains desired product for leacheate carries out post separating-purifying, product is white solid, and yield is 90%.
The nucleus magnetic hydrogen spectrum figure result of products obtained therefrom is:
1hNMR (600MHz, DMSO-d6): δ 8.33 (s, 1H), 7.89 (s, 1H), 7.55 (d, J=7.9Hz, 1H), 7.44 – 7.40 (m, 1H), 7.38 (td, J=7.7,1.5Hz, 1H).
Embodiment 9:
4-3-furans-2H-1, the synthesis of 2,3-triazole:
Reaction formula is:
Concrete steps are: in 50mL round-bottomed flask, add 0.33mmol2-furans nitroethylene, 0.36mmol sodiumazide, 0.03mmolAlCl
3, 2mLDMSO, after at room temperature magnetic agitation reacts 1 hour, be extracted with ethyl acetate reaction solution, organic layer is through saturated common salt water washing, after anhydrous sodium sulfate drying, namely pressure reducing and steaming solvent obtains thick product, and thick product ethyl acetate/petroleum ether=1:5 (V/V) namely obtains desired product for leacheate carries out post separating-purifying, product is white solid, and yield is 90%.
The nucleus magnetic hydrogen spectrum figure result of products obtained therefrom is:
1hNMR (600MHz, CDCl
3): δ 7.97 (s, 1H), 7.51 (d, J=1.2Hz, 1H), 6.85 (d, J=3.3Hz, 1H), 6.51 (m.1H).
Embodiment 10:
4-2-pyridyl-2H-1, the synthesis of 2,3-triazole:
Reaction formula is:
Concrete steps are: in 50mL round-bottomed flask, add 0.33mmol2-pyridyl nitroethylene, 0.36mmol sodiumazide, 0.03mmolAlCl
3, 2mLDMSO, after at room temperature magnetic agitation reacts 1 hour, be extracted with ethyl acetate reaction solution, organic layer is through saturated common salt water washing, after anhydrous sodium sulfate drying, namely pressure reducing and steaming solvent obtains thick product, and thick product ethyl acetate/petroleum ether=1:5 (V/V) namely obtains desired product for leacheate carries out post separating-purifying, product is white solid, and yield is 82%.
The nucleus magnetic hydrogen spectrum figure result of products obtained therefrom is: 1HNMR (400MHz, CDCl3) δ 8.72 (d, J=4.5Hz, 1H), 8.34 (s, 1H), 8.00 (d, J=7.1Hz, 1H), 7.82 (t, J=7.5Hz, 1H), 7.35 – 7.28 (m, 1H).
The present invention adopts AlCl cheap and easy to get
3as catalyzer, catalysis is carried out to the reaction of nitroolefin and sodiumazide, easily and effectively synthesize NH-1,2,3-triazole compounds, compared with existing method, reaction conditions of the present invention is gentle, the reaction times is short, security good, simple operation, reaction efficiency is high and catalyzer is cheap, is a kind of method with potential using value.
Above-mentioned example of executing does not limit the present invention in any form, all employings be equal to replace or etc. the technical scheme that obtains of the mode of little conversion, all drop in protection scope of the present invention.
Claims (10)
1. utilize aluminium salt catalysis stepwise synthesis NH-1, the method for 2,3-triazole, is characterized in that: under the catalysis of aluminium salt catalyst, and 1,3-Dipolar Cycloaddition occurs for nitroolefin and sodiumazide, and wherein nitroolefin is the nitroolefin of aryl or substituted aryl.
2. method according to claim 1, is characterized in that: described aluminium salt catalyst is selected from Al
2o
3, Al
2(SO
4)
3or AlCl
3.
3. method according to claim 2, is characterized in that: described aluminium salt catalyst is AlCl
3.
4., according to one of any described method of claims 1 to 3, it is characterized in that: aluminium salt catalyst mole dosage be the 0.05-0.2 of nitroolefin consumption doubly.
5. method according to claim 4, is characterized in that: aluminium salt catalyst mole dosage is 0.1 times of nitroolefin consumption.
6., according to one of any described method of claims 1 to 3, it is characterized in that: solvent for use is DMSO, acetonitrile, methyl alcohol, ethanol, toluene, trichloromethane or THF.
7. method according to claim 6, is characterized in that: solvent for use is DMSO.
8. method according to claim 6, is characterized in that: react and carry out in the temperature range of 0-110 DEG C.
9. method according to claim 8, is characterized in that: reaction is carried out at ambient temperature.
10. method according to claim 8, is characterized in that: the reaction times is 1-1.5 hour.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106749054A (en) * | 2016-12-07 | 2017-05-31 | 武汉工程大学 | The synthesis technique of the carboxylic acid compound of 1,2,3 triazoles of NH 4 |
| CN107698527A (en) * | 2017-10-11 | 2018-02-16 | 福建医科大学 | A kind of method that the triazole derivatives of 4 aryl NH 1,2,3 are catalyzed and synthesized under microwave radiation |
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| CN104001553A (en) * | 2014-06-20 | 2014-08-27 | 武汉工程大学 | N-substituted 1,2,3-triazole derivative/Cu(I) composite catalyst and synthesis and application thereof |
| CN104311495A (en) * | 2014-10-23 | 2015-01-28 | 西北大学 | Method for synthesizing NH-1,2,3-triazole |
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| CN104001553A (en) * | 2014-06-20 | 2014-08-27 | 武汉工程大学 | N-substituted 1,2,3-triazole derivative/Cu(I) composite catalyst and synthesis and application thereof |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106749054A (en) * | 2016-12-07 | 2017-05-31 | 武汉工程大学 | The synthesis technique of the carboxylic acid compound of 1,2,3 triazoles of NH 4 |
| CN107698527A (en) * | 2017-10-11 | 2018-02-16 | 福建医科大学 | A kind of method that the triazole derivatives of 4 aryl NH 1,2,3 are catalyzed and synthesized under microwave radiation |
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