CN105566235B - The method of the substep synthesis triazoles of NH 1,2,3 is catalyzed using aluminium salt - Google Patents
The method of the substep synthesis triazoles of NH 1,2,3 is catalyzed using aluminium salt Download PDFInfo
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- CN105566235B CN105566235B CN201610120763.9A CN201610120763A CN105566235B CN 105566235 B CN105566235 B CN 105566235B CN 201610120763 A CN201610120763 A CN 201610120763A CN 105566235 B CN105566235 B CN 105566235B
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- nitroolefin
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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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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 present invention relates to a kind of method for synthesizing the triazoles of NH 1,2,3 using aluminium salt catalysis substep, belong to organic and technical field of medicine synthesis, it is characterised in that：Under the catalysis of aluminium salt catalyst, with sodium azide 1,3 Dipolar Cycloadditions occur for nitroolefin, and wherein nitroolefin is the nitroolefin of aryl or substituted aryl.The beneficial effects of the invention are as follows：The present invention uses AlCl cheap and easy to get3、Al2O3Or Al2(SO4)3As catalyst, aluminium ion has activated the nitro of nitroolefin, reaction is set easily to carry out under mild conditions, improve the yield of reaction, easily and effectively synthesized NH 1,2,3 triazole compounds, compared with existing method, reaction condition of the present invention is gentle, reaction time section, security are good, easy to operate, reaction efficiency is high and catalyst is cheap, is a kind of method with potential using value.
Description
Technical field
The present invention relates to one kind using aluminium salt catalysis substep synthesis NH-1, the method for 2,3- triazoles, belong to organic and medicine
Synthesis technical field.
Technical background
1,2,3-triazoles compound is a kind of nitrogen-containing heterocycle compound with important physiologically active, is widely used in anti-corrosion
Agent, agricultural chemicals, optical material, dyestuff, HIV-1 inhibitor, antibiotic, selective β 3- class adrenal gland antagonist, antiviral drugs and
Anticonvulsant.Activity determination shows that 4- aryl-NH-1,2,3- triazole compounds can be used as human body methionine aminopeptidase to suppress
Agent.Nearest document report, some 4- aryl-NH-1,2,3- triazole compounds also there is IDO to suppress
Activity, is potential IDO inhibitor, therefore NH-1, and 2,3- triazole compounds can be used as treating cancer, Alzheimer disease,
A variety of mankind's major diseases such as cataract, wide market.
The synthesis of the 1,3- dipole Huisgen cycloaddition reactions of early stage organic azide and Terminal Acetylenes is that 1,4- bis- substitutes
With the mixture of the substituted triazoles of 1,5- bis-.The reaction needs to be connected with the conduct of strong electron-withdrawing group group on azido compound or alkynyl
Activated group, and need HTHP and longer reaction time.Therefore, in the synthesis substitution of Isosorbide-5-Nitrae-two -1,2,3-triazoles chemical combination
The application of thing is above very limited.
1971, Zefirow etc. was reported with NaN3It is raw material with nitroolefin or itrile group alkenes compounds, DMSO is
Solvent, synthesize 1H-1, the method for 2,3- triazole compounds.Although such reaction can be carried out at ambient temperature, must make
It is not easy to obtain by the use of the alkene containing nitro or itrile group as raw material, raw material, the versatility of reaction is limited, and yield is relatively low, and only 10%
~60%.1994, aryne was added TMSN by Moltzen groups3In, in N2The lower backflow 72h of protection, after silicon substrate is removed in washing,
Obtain NH-1,2,3- triazoles, yield 76%.Under no Cu (I) catalysis, reaction needs higher temperature and prolonged time
Stream.2004, Kim groups reported 2- pyridyl acetylenes and TMSN3Flowed back in DMF, synthesize 4- (2- pyridine radicals)-NH-1,
2,3- triazoles, yield 38%~71%.This method reaction temperature is higher, and yield is not high.The same year, Yamamoto etc. are reported
The 5mol% lower alkynes of CuI catalysis and TMSN3Between cycloaddition reaction.The DMF of synthetic method one and MeOH (V:V=9:1) it is
Solvent, 100 DEG C of 10~24h of reaction, synthesizes 4- substitutions-NH-1, the yield of 2,3- triazole compounds reaches as high as 95%.This method
The shortcomings that be that reaction temperature is higher, and the time is longer.2006, Barluenga etc. proposed a kind of with (E)-Beta-bromo virtue
Ethene and NaN3For Material synthesis 1H-1, the effective ways of 2,3- triazole compounds, this method is with Pd2(dba)3- Xantphos is
Catalyst, 14~24h is reacted in Dioxane or DMSO solvents, the completion conversion that can almost quantify.The shortcomings that this method, exists
The palladium catalyst series of costliness are used in reaction, and the reaction time is longer.The same year, Weinreb etc. are with a kind of 4- of commercialization
Tolyl-vinyl sulfone is raw material, in the MeOH systems under acid catalysis and NaN3Reaction, has synthesized a kind of valuable centre
Body β -4- methyl styrene nitrine (TSE-N3).The intermediate is obtained by the 1,3- Dipolar Cycloadditions of Cu (I)-catalysis
The 1,2,3- triazoles of TSE- protections.Protection group can be sloughed with KOBu-t in THF and obtain 4- substitutions -1H-1,2,3- triazoles, receive
Rate 61%~93%.The shortcomings that this method, is that synthesis step is more, and the reaction time is longer.2007, Cheng groups were to make by oneself
Arylalkyne nitrile be raw material, and NaN3Cycloaddition has synthesized one group of 4- aryl -5- itrile groups-NH-1,2,3- triazoles, and yield 50%~
80%.The shortcomings that this method, is to react the higher temperature of needs, and the more difficult synthesis of substrate.2008, Shi etc. reported one kind
With nitroolefin, NaN3Substitute the new synthesis road of-NH-1,2,3- triazoles for the three component reactions synthesis 4,5- bis- of raw material with aromatic aldehyde
Line.Reaction is catalyzed with L-proline, 8~10h is reacted at room temperature in DMSO, yield is typically 70%~90%.
In summary, above synthesis NH-1, the method for 2,3- triazole compounds generate difficult, reaction time length, reaction
Temperature height, low yield, the shortcomings of substrate is few or synthesis is difficult, material toxicity is big or security is poor, expensive catalyst can be fitted.
The content of the invention
To solve the deficiencies in the prior art, it is an object of the invention to provide a kind of reaction time is short, mild condition, safety
Property it is good, yield it is high utilization aluminium salt catalysis substep synthesis NH-1, the method for 2,3- triazoles.
To reach above-mentioned purpose, the present invention is achieved by the following technical solutions：Substep is catalyzed using aluminium salt to close
Into NH-1, the method for 2,3- triazoles, it is characterised in that：Under the catalysis of aluminium salt catalyst, nitroolefin occurs with sodium azide
1,3- Dipolar Cycloaddition, wherein nitroolefin are the nitroolefin of aryl or substituted aryl.
By such scheme, described aluminium salt catalyst is selected from Al2O3,Al2(SO4)3Or AlCl3。
By such scheme, described aluminium salt catalyst is AlCl3。
By such scheme, aluminium salt catalyst mole dosage is 0.05-0.2 times of nitroolefin dosage.
By such scheme, aluminium salt catalyst mole dosage is 0.1 times of nitroolefin dosage.
By such scheme, solvent for use DMSO, acetonitrile, methanol, ethanol, toluene, chloroform or THF.
By such scheme, solvent for use DMSO.
By such scheme, react and carried out within the temperature range of 0-110 DEG C.
By such scheme, reaction is carried out at ambient temperature.
By such scheme, the reaction time is 1-1.5 hours.
Specific reaction equation involved in the present invention is as shown in formula I：
The beneficial effects of the invention are as follows：The present invention uses AlCl cheap and easy to get3、Al2O3Or Al2(SO4)3As catalysis
Agent, aluminium ion have activated the nitro of nitroolefin, reaction is easily carried out under mild conditions, improve the production of reaction
Rate, easily and effectively synthesized NH-1,2,3- triazole compounds, compared with existing method, reaction condition of the present invention
Gently, reaction time section, security are good, easy to operate, reaction efficiency is high and catalyst is cheap, are that one kind has potential application valency
The method of value.
Embodiment
For a better understanding of the present invention, with reference to the embodiment content that the present invention is furture elucidated, but the present invention
Content is not limited solely to the following examples.
Embodiment 1：
The synthesis of 4- phenyl -2H-1,2,3- triazoles：
Reaction equation is：
Concretely comprise the following steps：Added into 50mL round-bottomed flasks 0.33mmol nitrostyrolenes, 0.36mmol sodium azide,
0.03mmol AlCl3, 2mL DMSO, at room temperature magnetic agitation react 1 hour after, reaction solution is extracted with ethyl acetate, has
Machine layer is through saturated common salt water washing, and after anhydrous sodium sulfate drying, decompression boils off solvent and produces crude product, crude product acetic acid second
Ester/petroleum ether=1:5 (V/V) are purified for leacheate progress post separation and are produced required product, and product is white solid, and yield is
94%.
The nucleus magnetic hydrogen spectrum figure result of products obtained therefrom is：1H NMR(600MHz,DMSO-d6):δ8.32(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：
The synthesis of 4- phenyl -2H-1,2,3- triazoles：
Reaction equation is：
Concretely comprise the following steps：Added into 50mL round-bottomed flasks 0.33mmol nitrostyrolenes, 0.36mmol sodium azide,
0.03mmol Al2O3, 2mL DMSO, at room temperature magnetic agitation react 1 hour after, reaction solution is extracted with ethyl acetate, has
Machine layer is through saturated common salt water washing, and after anhydrous sodium sulfate drying, decompression boils off solvent and produces crude product, crude product acetic acid second
Ester/petroleum ether=1:5 (V/V) are purified for leacheate progress post separation and are produced required product, and product is white solid, and yield is
73%.
The nucleus magnetic hydrogen spectrum figure result of products obtained therefrom is：1H NMR(600MHz,DMSO-d6):δ8.32(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：
The synthesis of 4- phenyl -2H-1,2,3- triazoles：
Reaction equation is：
Concretely comprise the following steps：Added into 50mL round-bottomed flasks 0.33mmol nitrostyrolenes, 0.36mmol sodium azide,
0.03mmolAl2(SO4)3, 2mL DMSO, at room temperature magnetic agitation react 1 hour after, reaction solution is extracted with ethyl acetate,
Organic layer is through saturated common salt water washing, and after anhydrous sodium sulfate drying, decompression boils off solvent and produces crude product, crude product acetic acid second
Ester/petroleum ether=1:5 (V/V) are purified for leacheate progress post separation and are produced required product, and product is white solid, and yield is
75%.
The nucleus magnetic hydrogen spectrum figure result of products obtained therefrom is：1H NMR(600MHz,DMSO-d6):δ8.32(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：
The synthesis of 4- p-methylphenyl -2H-1,2,3- triazoles：
Reaction equation is：
Concretely comprise the following steps：0.33mmol nitros p-methylstyrene, 0.36mmol nitrine are added into 50mL round-bottomed flasks
Change sodium, 0.03mmolAlCl3, 2mL DMSO, at room temperature magnetic agitation react 1 hour after, reaction is extracted with ethyl acetate
Liquid, organic layer is through saturated common salt water washing, and after anhydrous sodium sulfate drying, decompression boils off solvent and produces crude product, crude product second
Acetoacetic ester/petroleum ether=1:5 (V/V) are that leacheate carries out post separation and purifies and produce required product, and product is white solid, yield
For 90%.
The nucleus magnetic hydrogen spectrum figure result of products obtained therefrom is：1H NMR(600MHz,DMSO-d6):δ8.25(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- triazoles：
Reaction equation is:
Concretely comprise the following steps：0.33mmol nitro 2,4 dichloro benzene bases ethene, 0.36mmol are added into 50mL round-bottomed flasks
Sodium azide, 0.03mmolAlCl3, 2mL DMSO, at room temperature magnetic agitation react 1 hour after, be extracted with ethyl acetate
Reaction solution, organic layer is through saturated common salt water washing, and after anhydrous sodium sulfate drying, decompression boils off solvent and produces crude product, crude product
With ethyl acetate/petroleum ether=1:5 (V/V) are purified for leacheate progress post separation and are produced required product, and product is white solid,
Yield is 95%.
The nucleus magnetic hydrogen spectrum figure result of products obtained therefrom is：1H NMR(600MHz,DMSO-d6):δ8.38(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：
The synthesis of 4- O-Nitrophenylfluorone -2H-1,2,3- triazoles：
Reaction equation is：
Concretely comprise the following steps：0.33mmol nitro O-Nitrophenylfluorones ethene is added into 50mL round-bottomed flasks, 0.36mmol is folded
Sodium nitride, 0.03mmolAlCl3, 2mL DMSO, after magnetic agitation reacted for 1 hour at room temperature, be extracted with ethyl acetate anti-
Answer liquid, organic layer is through saturated common salt water washing, and after anhydrous sodium sulfate drying, decompression boils off solvent and produces crude product, and crude product is used
Ethyl acetate/petroleum ether=1:5 (V/V) are purified for leacheate progress post separation and are produced required product, and product is white solid, are received
Rate is 85%.
The nucleus magnetic hydrogen spectrum figure result of products obtained therefrom is：1H NMR(600MHz,DMSO-d6):δ8.24(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：
The synthesis of 4- o-bromophenyl -2H-1,2,3- triazoles：
Reaction equation is：
Concretely comprise the following steps：0.33mmol nitro o-bromophenyls ethene, 0.36mmol nitrine are added into 50mL round-bottomed flasks
Change sodium, 0.03mmolAlCl3, 2mL DMSO, at room temperature magnetic agitation react 1 hour after, reaction is extracted with ethyl acetate
Liquid, organic layer is through saturated common salt water washing, and after anhydrous sodium sulfate drying, decompression boils off solvent and produces crude product, crude product second
Acetoacetic ester/petroleum ether=1:5 (V/V) are that leacheate carries out post separation and purifies and produce required product, and product is white solid, yield
For 95%.
The nucleus magnetic hydrogen spectrum figure result of products obtained therefrom is：1H NMR(600MHz,CDCl3):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：
The synthesis of 4- Chloro-O-Phenyl -2H-1,2,3- triazoles：
Reaction equation is：
Concretely comprise the following steps：0.33mmol nitro Chloro-O-Phenyls ethene, 0.36mmol nitrine are added into 50mL round-bottomed flasks
Change sodium, 0.03mmolAlCl3, 2mL DMSO, at room temperature magnetic agitation react 1 hour after, reaction is extracted with ethyl acetate
Liquid, organic layer is through saturated common salt water washing, and after anhydrous sodium sulfate drying, decompression boils off solvent and produces crude product, crude product second
Acetoacetic ester/petroleum ether=1:5 (V/V) are that leacheate carries out post separation and purifies and produce required product, and product is white solid, yield
For 90%.
The nucleus magnetic hydrogen spectrum figure result of products obtained therefrom is：1H NMR(600MHz,DMSO-d6):δ8.33(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：
The synthesis of 4-3- furans -2H-1,2,3- triazoles：
Reaction equation is：
Concretely comprise the following steps：0.33mmol 2- furans nitroethylene, 0.36mmol Azides are added into 50mL round-bottomed flasks
Sodium, 0.03mmolAlCl3, 2mL DMSO, at room temperature magnetic agitation react 1 hour after, reaction solution is extracted with ethyl acetate,
Organic layer is through saturated common salt water washing, and after anhydrous sodium sulfate drying, decompression boils off solvent and produces crude product, crude product acetic acid second
Ester/petroleum ether=1:5 (V/V) are purified for leacheate progress post separation and are produced required product, and product is white solid, and yield is
90%.
The nucleus magnetic hydrogen spectrum figure result of products obtained therefrom is：1H NMR(600MHz,CDCl3):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：
The synthesis of 4-2- pyridine radicals -2H-1,2,3- triazoles：
Reaction equation is：
Concretely comprise the following steps：0.33mmol 2- pyridine radicals nitroethylene, 0.36mmol nitrine are added into 50mL round-bottomed flasks
Change sodium, 0.03mmolAlCl3, 2mL DMSO, at room temperature magnetic agitation react 1 hour after, reaction is extracted with ethyl acetate
Liquid, organic layer is through saturated common salt water washing, and after anhydrous sodium sulfate drying, decompression boils off solvent and produces crude product, crude product second
Acetoacetic ester/petroleum ether=1:5 (V/V) are that leacheate carries out post separation and purifies and produce required product, and product is white solid, yield
For 82%.
The nucleus magnetic hydrogen spectrum figure result of products obtained therefrom is：1H NMR (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 uses AlCl cheap and easy to get3As catalyst, the reaction to nitroolefin and sodium azide is urged
Change, easily and effectively synthesize NH-1,2,3- triazole compounds, compared with existing method, reaction condition of the present invention is gentle,
Reaction time is short, security is good, simple operation, reaction efficiency is high and catalyst is cheap, is a kind of to have potential using value
Method.
It is above-mentioned to apply example the invention is not limited in any way, it is all using equivalent substitution or to wait what is obtained by the way of small conversion
Technical scheme, all fall within protection scope of the present invention.
Claims (8)
1. catalyze and synthesize NH-1, the method for 2,3- triazoles using aluminium salt, it is characterised in that：In aluminium salt catalyst AlCl3Catalysis
Under, with sodium azide 1,3- Dipolar Cycloadditions occur for nitroolefin, and wherein nitroolefin is the nitre of aryl or substituted aryl
Base alkene.
2. method according to claim 1, it is characterised in that：Aluminium salt catalyst mole dosage is nitroolefin dosage
0.05-0.2 times.
3. method according to claim 2, it is characterised in that：Aluminium salt catalyst mole dosage is the 0.1 of nitroolefin dosage
Times.
4. method according to claim 1, it is characterised in that：Solvent for use is DMSO, acetonitrile, methanol, ethanol, toluene, three
Chloromethanes or THF.
5. method according to claim 4, it is characterised in that：Solvent for use is DMSO.
6. method according to claim 4, it is characterised in that：Reaction is carried out within the temperature range of 0-110 DEG C.
7. method according to claim 6, it is characterised in that：Reaction is carried out at ambient temperature.
8. method according to claim 6, it is characterised in that：Reaction time is 1-1.5 hours.
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