CN108440451A - The preparation method of 4- (1- tert-butoxycarbonyl-piperazine -4- bases) aniline - Google Patents
The preparation method of 4- (1- tert-butoxycarbonyl-piperazine -4- bases) aniline Download PDFInfo
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- CN108440451A CN108440451A CN201810215435.6A CN201810215435A CN108440451A CN 108440451 A CN108440451 A CN 108440451A CN 201810215435 A CN201810215435 A CN 201810215435A CN 108440451 A CN108440451 A CN 108440451A
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/205—Radicals derived from carbonic acid
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Abstract
The invention discloses a kind of preparation methods of 4 (1 tert-butoxycarbonyl-piperazine, 4 base) aniline.The preparation method of described 4 (1 tert-butoxycarbonyl-piperazine, 4 base) aniline comprises the step of:By the aniline, 1 carboxylate of piperazine, acridinium salt photochemical catalyst are added in solvent, and existing for oxidant under the conditions of carries out illumination reaction, generates 4 (1 tert-butoxycarbonyl-piperazine, 4 base) aniline.Preparation method one-step synthesis 4 (1 tert-butoxycarbonyl-piperazine, 4 base) aniline of 4 (1 tert-butoxycarbonyl-piperazine, 4 base) aniline of the invention, on the one hand the synthesis path of described 4 (1 tert-butoxycarbonyl-piperazine, 4 base) aniline is effectively shortened, the generation for effectively reducing by-product improves the yield of target product;On the other hand photochemical catalyst and oxidant have only been used so that preparation method safety and environmental protection of the present invention, it is at low cost.
Description
Technical field
The invention belongs to organic medicinal chemistry technical fields, particularly relate to a kind of 4- (1- tert-butoxycarbonyl-piperazines-
4- yls) aniline preparation method.
Background technology
4- (1- tert-butoxycarbonyl-piperazine -4- bases) aniline is a kind of important industrial chemicals.Conventional synthesis 4- (uncles 1-
Butoxy carbonyl piperazine -4- bases) there are the deficiencies of high pollution, low atom economy etc. for the method for aniline, in order to overcome conventional synthesis side
The deficiency of method is currently suggested a kind of photocatalysis to synthesize 4- (1- tert-butoxycarbonyl-piperazine -4- bases) aniline, and specific chemistry is anti-
Answer formula as follows:
The current photocatalytic synthesis is linear by two steps at the method for 4- (1- tert-butoxycarbonyl-piperazine -4- bases) aniline
Reaction, the first step are the coupling reactions of metal catalytic, and second step is the hydrogenation process of palladium carbon catalysis.In the photocatalytic synthesis at mistake
Heavy metal has been used in journey, and has used the hydrogen of the dangerous factor of production.Therefore, at present photocatalytic synthesis at 4- (the tertiary fourths of 1-
Oxygen carbonyl piperazine -4- bases) that there are synthetic routes is relatively long for the method for aniline, and by-product is relatively more, is produced so as to cause target
Object yield is low, and the cost is relatively high, and there are certain harmfulness to environment and health.
Invention content
It is an object of the invention to overcome the above-mentioned deficiency of the prior art, a kind of 4- (1- tert-butoxycarbonyl-piperazines -4- are provided
Base) aniline preparation method, with solve existing photocatalytic synthesis at 4- (1- tert-butoxycarbonyl-piperazine -4- bases) aniline method exist
Synthetic route is long, and target product yield is low, there is technical issues that environment and health certain.
In order to achieve the above-mentioned object of the invention, the present invention provides a kind of 4- (1- tert-butoxycarbonyl-piperazine -4- bases) aniline
Preparation method.The preparation method of 4- (1- tert-butoxycarbonyl-piperazine -4- bases) aniline includes the following steps:
Aniline, piperazine -1- carboxylates, acridinium salt photochemical catalyst are added in solvent, and existing for oxidant
Under the conditions of carry out illumination reaction, generate 4- (1- tert-butoxycarbonyl-piperazine -4- bases) aniline.
Compared with prior art, the preparation method of 4- (1- tert-butoxycarbonyl-piperazine -4- bases) aniline of the present invention uses acridine
Salt is as photochemical catalyst, under the conditions of existing for oxidant so that described in aniline and piperazine -1- carboxylate one-step synthesis
On the one hand 4- (1- tert-butoxycarbonyl-piperazine -4- bases) aniline effectively shortens the 4- (1- tert-butoxycarbonyl-piperazine -4- bases) benzene
The synthesis path of amine effectively reduces the generation of by-product, improves the yield of target product;On the other hand light has only been used to urge
Agent and oxidant avoid the use to heavy metal and hydrogen environment, to which the peace of preparation method of the present invention be effectively ensured
Loopful is protected, at low cost.
Specific implementation mode
In order to make technical problems, technical solutions and advantageous effects to be solved by the present invention be more clearly understood, below in conjunction with
Embodiment, the present invention will be described in further detail.It should be appreciated that specific embodiment described herein is only used to explain
The present invention is not intended to limit the present invention.
The present invention provides a kind of preparation methods of 4- (1- tert-butoxycarbonyl-piperazine -4- bases) aniline.4- (the tertiary fourths of 1-
Oxygen carbonyl piperazine -4- bases) preparation method of aniline includes the following steps:
The aniline, piperazine -1- carboxylates, acridinium salt photochemical catalyst are added in solvent, and are deposited in oxidant
Illumination reaction is carried out under the conditions, generates 4- (1- tert-butoxycarbonyl-piperazine -4- bases) aniline.
Specifically, in the illumination reaction, the aniline, piperazine -1- carboxylates illumination effect under and acridine
Under the catalytic action of salt photochemical catalyst and under the conditions of oxidant is existing, product Compound 4- (1- tert-butoxycarbonyl-piperazines-are generated
4- yls) aniline.The chemical equation of the illumination reaction is as follows:
Wherein, the acridinium salt promotes the aniline, piperazine -1- carboxylates to be condensed under illumination condition
Reaction.In one embodiment, the acridinium salt photochemical catalyst includes at least one of following structural formula:
The acridinium salt photochemical catalyst high catalytic efficiency of the structural formula, to realize one-step synthesis target product 4- (uncles 1-
Butoxy carbonyl piperazine -4- bases) aniline, while avoiding using heavy metal catalyst so that the illumination reaction Environmental Safety, and
And it is at low cost.In another embodiment, the molar concentration rate for controlling the acridinium salt photochemical catalyst and the aniline is (0.05-
0.50):(1-10).Since the acridinium salt using for example described structural formula of acridinium salt is as catalyst, acridinium salt is effectively reduced
Usage amount, and improve photocatalysis efficiency.
In the light-catalyzed reaction, due to using acridinium salt as photochemical catalyst, in one embodiment, the light
It is to use visible light illumination according to reaction, if illumination wavelength is 380nm-750nm.It that is to say and use wavelength for 380nm-750nm's
Visible light exposure contains the reaction solution system of the aniline, piperazine -1- carboxylates and acridinium salt and oxidant, opens
Dynamic condensation reaction between the aniline, piperazine -1- carboxylates, it should be appreciated that exposure or light application time are answered
This is enough, be that is to say so that the reaction between the aniline, piperazine -1- carboxylates is fully reacted.Such as specific
In embodiment, the exposure or light application time can be 10h hours or more.
In the light-catalyzed reaction, the oxidant in reaction system assists the photocatalysis effect of the acridinium salt.One implements
In example, the oxidant includes at least one of peroxide, metal oxide, persulfide, nitrogen oxides, oxygen.When
When the oxidant is peroxide, metal oxide, persulfide, at least one of nitrogen oxides, the oxidant with
The molar concentration rate of the aniline is (1-10):(1-10), such as the specific can be that 1:2.At this point, the light-catalyzed reaction can be with
Be to be reacted in the environment such as argon gas, nitrogen, hydrogen, naturally it is also possible to carried out in the environment containing oxygen.When the oxygen
When agent is oxygen, the illumination reaction carries out in air or in oxygen.In a particular embodiment, the peroxide
For at least one of tert-Butanol peroxide, benzoyl peroxide, hydrogen peroxide;The metal oxide is potassium permanganate, titanium dioxide
At least one of manganese, chromium trioxide, di-iron trioxide;The persulfide is diphenyl disulfide, hydrogen persulfide, 4- methyl two
At least one of diphenyl disulfide ether, 2,6- dimethyl diphenyl disulfides;The nitrogen oxides is 2,2,6,6- tetramethyl piperidines-
Nitrogen-oxide, N-methyl morpholine oxide, 2,2,4,6,6- pentamethvls-nitrogen-oxide, 2,2,6,6- tetramethyl -5- hydroxyls
At least one of phenylpiperidines-nitrogen-oxide.
On the basis of the various embodiments described above, in an embodiment, the aniline, piperazine -1- carboxylates are controlled
Molar density is (1-10):(1-10), it is specific such as 1:1.In another embodiment, the aniline rubbing in the solvent is controlled
Your concentration can be 0.05-0.50mol/L.By the concentration and concentration that control the aniline, piperazine -1- carboxylates
Than improving the forward reaction efficiency between two reactants, providing target product 4- (1- tert-butoxycarbonyl-piperazine -4- bases) aniline
Yield.
In addition, the solvent in the light-catalyzed reaction include toluene, acetone, ethyl acetate, dichloromethane, dichloroethanes,
At least one of ethyl alcohol, trifluoroacetic acid, benzene, tetrahydrofuran, ether, water, dimethyl sulfone, N,N-dimethylformamide.It selects
The solvent, ensure that the positive of the acridinium salt light-catalyzed reaction carries out, and provide the yield of target product.
Further include to 4- described in target product (1- tert-butoxycarbonyl-piperazine -4- bases) benzene after waiting for the illumination reaction
The step of amine is purified.The method purified to the 4- (1- tert-butoxycarbonyl-piperazine -4- bases) Aniline product can be by
According to the purification process purifying of existing synthesis 4- (1- tert-butoxycarbonyl-piperazine -4- bases) aniline.
The preparation method of 4- (1- tert-butoxycarbonyl-piperazine -4- bases) aniline uses acridinium salt as photochemical catalyst, and
Coordinate oxidant, the lower one-step synthesis for realizing 4- (1- tert-butoxycarbonyl-piperazine -4- bases) aniline is excited using illumination, to effectively
The synthesis cost for reducing 4- (1- tert-butoxycarbonyl-piperazine -4- bases) aniline, effectively improves target product 4- (1- tertbutyloxycarbonyls
Piperazine -4- bases) aniline yield.In addition, the preparation method condition is easily-controllable, safety and environmental protection, synthesis target product yield is stablized,
It is suitable for industrialized production.
In conjunction with embodiment, the present invention will be described in further detail.
Embodiment 1
The present embodiment provides a kind of preparation methods of 4- (1- tert-butoxycarbonyl-piperazine -4- bases) aniline.4- (the tertiary fourths of 1-
Oxygen carbonyl piperazine -4- bases) aniline synthetic method:
By aniline, piperazine -1- carboxylates, acridinium salt visible light catalyst, 2,2,6,6- tetramethyl piperidines-nitrogen -
Oxide is added in anhydrous dichloroethanes, then uses replacement of oxygen reaction environment three times, is irradiated with blue led, the reaction time
For 10h.After completion of the reaction, filtrate is spin-dried for, column chromatography for separation, obtains target product, colorless white solid, yield 95%.
Wherein, aniline, piperazine -1- carboxylates, acridinium salt, 2,2,6,6- tetramethyl piperidines-nitrogen-oxide and nothing
Water dichloroethanes is added according to following proportionate relationship:In the anhydrous dichloroethanes of every 2mL, addition 0.2mmol, the aniline of 1.0eq,
Piperazine -1- carboxylates, the 0.01mmol of 0.2mmol, 1.0eq, acridinium salt, the 0.1mmol of 0.1eq, the tetramethyl of 0.5eq
Piperidine nitroxide.
The nuclear-magnetism and mass spectrum of target product:
1H-NMR(300MHz,d6-DMSO):1.41(9H,s),3.29(4H,dd),3.32(4H,dd),4.50(2H,s),
5.95(2H,d),6.65(2H,d).HR-MS m/z:278.1869。
By nuclear-magnetism measurement result it is found that target product is 4- (1- tert-butoxycarbonyl-piperazine -4- bases) aniline.
Embodiment 2
The present embodiment provides a kind of preparation methods of 4- (1- tert-butoxycarbonyl-piperazine -4- bases) aniline.4- (the tertiary fourths of 1-
Oxygen carbonyl piperazine -4- bases) aniline synthetic method:
By aniline, piperazine -1- carboxylates, acridinium salt visible light catalyst, 2,2,4,6,6- pentamethvls -
Nitrogen-oxide is added in anhydrous dichloroethanes, then uses replacement of oxygen reaction environment three times, is irradiated with blue led, when reaction
Between be 10h.After completion of the reaction, filtrate is spin-dried for, column chromatography for separation, obtains target product, colorless white solid, yield 93%.
Wherein, aniline, piperazine -1- carboxylates, acridinium salt, 2,2,4,6,6- pentamethvls-nitrogen-oxide and
Anhydrous dichloroethanes is added according to following proportionate relationship:In the anhydrous dichloroethanes of every 2mL, addition 0.2mmol, the aniline of 1.0eq,
Piperazine -1- carboxylates, the 0.01mmol of 0.2mmol, 1.0eq, acridinium salt, the 0.1mmol of 0.1eq, the 2,2 of 0.5eq,
4,6,6- pentamethvls-nitrogen-oxide.
The nuclear-magnetism and mass spectrum of target product:
1H-NMR(300MHz,d6-DMSO):1.41(9H,s),3.29(4H,dd),3.32(4H,dd),4.50(2H,s),
5.95(2H,d),6.65(2H,d).HR-MS m/z:278.1869。
By nuclear-magnetism measurement result it is found that target product is 4- (1- tert-butoxycarbonyl-piperazine -4- bases) aniline.
Embodiment 3
The present embodiment provides a kind of preparation methods of 4- (1- tert-butoxycarbonyl-piperazine -4- bases) aniline.4- (the tertiary fourths of 1-
Oxygen carbonyl piperazine -4- bases) aniline synthetic method:
By aniline, piperazine -1- carboxylates, acridinium salt visible light catalyst, 2,2,6,6- tetramethyl -5- hydroxyl piperazines
Pyridine-nitrogen-oxide is added in anhydrous dichloroethanes, then uses replacement of oxygen reaction environment three times, is irradiated with blue led, instead
It is 10h between seasonable.After completion of the reaction, filtrate is spin-dried for, column chromatography for separation, obtains target product, colorless white solid, yield 93%.
Wherein, aniline, piperazine -1- carboxylates, acridinium salt, tetramethyl piperidine nitrogen oxides and anhydrous dichloroethanes
It is added according to following proportionate relationship:Per in the anhydrous dichloroethanes of 2mL, 0.2mmol, aniline, the 0.2mmol of 1.0eq are added,
Piperazine -1- carboxylates, the 0.01mmol of 1.0eq, acridinium salt, the 0.1mmol of 0.1eq, the 2,2,6,6- tetramethyls of 0.5eq
Base -5- hydroxy piperidines-nitrogen-oxide.
The nuclear-magnetism and mass spectrum of target product:
1H-NMR(300MHz,d6-DMSO):1.41(9H,s),3.29(4H,dd),3.32(4H,dd),4.50(2H,s),
5.95(2H,d),6.65(2H,d).HR-MS m/z:278.1869。
By nuclear-magnetism measurement result it is found that target product is 4- (1- tert-butoxycarbonyl-piperazine -4- bases) aniline.
Embodiment 4
The present embodiment provides a kind of preparation methods of 4- (1- tert-butoxycarbonyl-piperazine -4- bases) aniline.4- (the tertiary fourths of 1-
Oxygen carbonyl piperazine -4- bases) aniline synthetic method:
Anhydrous two chloroethene is added in aniline, piperazine -1- carboxylates, acridinium salt visible light catalyst, potassium permanganate
In alkane, then uses replacement of oxygen reaction environment three times, irradiated with blue led, reaction time 15h.After completion of the reaction, filtrate
It is spin-dried for, column chromatography for separation, obtains target product, colorless white solid, yield 92%.
Wherein, aniline, piperazine -1- carboxylates, acridinium salt, potassium permanganate and anhydrous dichloroethanes are according to following ratio
Example relationship addition:Per in the anhydrous dichloroethanes of 2mL, 0.2mmol, aniline, the 0.2mmol of 1.0eq, the piperazine -1- of 1.0eq are added
Carboxylate, 0.005mmol, the acridinium salt of 0.1eq, the potassium permanganate of 0.02mmol.
The nuclear-magnetism and mass spectrum of target product:
1H-NMR(300MHz,d6-DMSO):1.41(9H,s),3.29(4H,dd),3.32(4H,dd),4.50(2H,s),
5.95(2H,d),6.65(2H,d).HR-MS m/z:278.1869.
By nuclear-magnetism measurement result it is found that target product is 4- (1- tert-butoxycarbonyl-piperazine -4- bases) aniline.
Embodiment 5
The present embodiment provides a kind of preparation methods of 4- (1- tert-butoxycarbonyl-piperazine -4- bases) aniline.4- (the tertiary fourths of 1-
Oxygen carbonyl piperazine -4- bases) aniline synthetic method:
Anhydrous dichloro is added in aniline, piperazine -1- carboxylates, acridinium salt visible light catalyst, diphenyl disulfide
In ethane, then uses replacement of oxygen reaction environment three times, irradiated with blue led, reaction time 10h.After completion of the reaction, it filters
Liquid is spin-dried for, column chromatography for separation, obtains target product, colorless white solid, yield 94%.
Wherein, aniline, piperazine -1- carboxylates, acridinium salt, diphenyl disulfide and anhydrous dichloroethanes are according to as follows
Proportionate relationship is added:Per in the anhydrous dichloroethanes of 2mL, 0.2mmol, aniline, the 0.2mmol of 1.0eq, the piperazine-of 1.0eq are added
1- carboxylates, 0.05mmol, acridinium salt, the 0.02mmol of 0.1eq, diphenyl disulfide.
The nuclear-magnetism and mass spectrum of target product:
1H-NMR(300MHz,d6-DMSO):1.41(9H,s),3.29(4H,dd),3.32(4H,dd),4.50(2H,s),
5.95(2H,d),6.65(2H,d).HR-MS m/z:278.1869.
By nuclear-magnetism measurement result it is found that target product is 4- (1- tert-butoxycarbonyl-piperazine -4- bases) aniline.
Embodiment 6
The present embodiment provides a kind of preparation methods of 4- (1- tert-butoxycarbonyl-piperazine -4- bases) aniline.4- (the tertiary fourths of 1-
Oxygen carbonyl piperazine -4- bases) aniline synthetic method:
Aniline, piperazine -1- carboxylates, acridinium salt visible light catalyst are added in anhydrous dichloroethanes, then
Three times using replacement of oxygen reaction environment, it is irradiated with blue led, reaction time 10h.After completion of the reaction, filtrate is spin-dried for, column layer
Analysis separation, obtains target product, colorless white solid, yield 91%.
Wherein, aniline, piperazine -1- carboxylates, acridinium salt and anhydrous dichloroethanes add according to following proportionate relationship
Add:Per in the anhydrous dichloroethanes of 2mL, 0.2mmol, aniline, the 0.2mmol of 1.0eq, the tertiary fourth of piperazine -1- formic acid of 1.0eq are added
Base ester, 0.05mmol, the acridinium salt of 0.1eq.
The nuclear-magnetism and mass spectrum of target product:
1H-NMR(300MHz,d6-DMSO):1.41(9H,s),3.29(4H,dd),3.32(4H,dd),4.50(2H,s),
5.95(2H,d),6.65(2H,d).HR-MS m/z:278.1869.
By nuclear-magnetism measurement result it is found that target product is 4- (1- tert-butoxycarbonyl-piperazine -4- bases) aniline.
The foregoing is merely illustrative of the preferred embodiments of the present invention, is not intended to limit the invention, all essences in the present invention
All any modification, equivalent and improvement etc., should all be included in the protection scope of the present invention made by within refreshing and principle.
Claims (9)
1. a kind of preparation method of 4- (1- tert-butoxycarbonyl-piperazine -4- bases) aniline, includes the following steps:
Aniline, piperazine -1- carboxylates, acridinium salt photochemical catalyst are added in solvent, and the condition existing for oxidant
Lower carry out illumination reaction generates 4- (1- tert-butoxycarbonyl-piperazine -4- bases) aniline.
2. preparation method according to claim 1, it is characterised in that:The acridinium salt photochemical catalyst includes following structural formula
At least one of:
3. preparation method according to claim 1 or 2, it is characterised in that:The acridinium salt photochemical catalyst and the aniline
Molar concentration rate be (0.05-0.50):(1-10).
4. preparation method according to claim 1 or 2, it is characterised in that:The illumination wavelength of the illumination reaction is
The visible light of 380nm-750nm.
5. preparation method according to claim 1, it is characterised in that:The oxidant includes peroxide, metal oxidation
At least one of object, persulfide, nitrogen oxides, oxygen.
6. preparation method according to claim 5, it is characterised in that:The oxidant be peroxide, metal oxide,
When at least one of persulfide, nitrogen oxides, the molar concentration rate of the oxidant and the aniline is (1-10):(1-
10)。
7. according to 1,2,5,6 any one of them preparation method of claim, it is characterised in that:The peroxide is peroxide uncle
At least one of butanol, benzoyl peroxide, hydrogen peroxide;
The metal oxide is at least one of potassium permanganate, manganese dioxide, chromium trioxide, di-iron trioxide;
The persulfide is in diphenyl disulfide, hydrogen persulfide, 4- methyldiphenyls disulfide, 2,6- dimethyl diphenyl disulfides
At least one;
The nitrogen oxides is 2,2,6,6- tetramethyl piperidines-nitrogen-oxide, N-methyl morpholine oxide, 2,2,4,6,6- five
At least one of methyl piperidine-nitrogen-oxide, 2,2,6,6- tetramethyls -5- hydroxy piperidines-nitrogen-oxide.
8. according to 1,2,5,6 any one of them preparation method of claim, it is characterised in that:The solvent includes toluene, third
Ketone, ethyl acetate, dichloromethane, dichloroethanes, ethyl alcohol, trifluoroacetic acid, benzene, tetrahydrofuran, ether, water, dimethyl sulfone, N, N-
At least one of dimethylformamide.
9. according to 1,2,5,6 any one of them preparation method of claim, it is characterised in that:The aniline, piperazine -1- formic acid
The molar concentration rate of tertiary butyl ester is (1-10):(1-10);And/or
Molar concentration rate of the aniline in the solvent is 0.05-0.50mol/L.
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107973800A (en) * | 2017-12-29 | 2018-05-01 | 深圳蓝新科技有限公司 | The preparation method of Zaleplon |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1738615A (en) * | 2002-11-15 | 2006-02-22 | 沃泰克斯药物股份有限公司 | Diaminotriazoles useful as inhibitors of protein kinases |
WO2016196816A1 (en) * | 2015-06-03 | 2016-12-08 | The University Of North Carolina At Chapel Hill | Photoredox-catalyzed direct c-h functionalization of arenes |
CN106905245A (en) * | 2015-12-23 | 2017-06-30 | 正大天晴药业集团股份有限公司 | The dibasic pyrimidines of 2,4- |
-
2018
- 2018-03-15 CN CN201810215435.6A patent/CN108440451B/en active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1738615A (en) * | 2002-11-15 | 2006-02-22 | 沃泰克斯药物股份有限公司 | Diaminotriazoles useful as inhibitors of protein kinases |
WO2016196816A1 (en) * | 2015-06-03 | 2016-12-08 | The University Of North Carolina At Chapel Hill | Photoredox-catalyzed direct c-h functionalization of arenes |
CN106905245A (en) * | 2015-12-23 | 2017-06-30 | 正大天晴药业集团股份有限公司 | The dibasic pyrimidines of 2,4- |
Non-Patent Citations (1)
Title |
---|
PATEL, KAVITKUMAR N.等: "Design, synthesis and antitubercular evaluation of novel series of N-[4-(piperazin-1-yl)phenyl]cinnamamide derivatives", 《EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY》 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107973800A (en) * | 2017-12-29 | 2018-05-01 | 深圳蓝新科技有限公司 | The preparation method of Zaleplon |
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