CN110128345A - A kind of preparation method of e derivatives - Google Patents
A kind of preparation method of e derivatives Download PDFInfo
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- CN110128345A CN110128345A CN201910392049.9A CN201910392049A CN110128345A CN 110128345 A CN110128345 A CN 110128345A CN 201910392049 A CN201910392049 A CN 201910392049A CN 110128345 A CN110128345 A CN 110128345A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
- C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
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Abstract
The present invention relates to a kind of preparation methods of e derivatives.This method is by 1- substituent group -3- trifluoromethyl -5- pyrazolone and substituted benzaldehyde and the appropriate thick silica gel of additive SILVER REAGENT is added, agitation grinding obtains compound 4, the bis- (1- aryl -3- Trifluoromethyl-1s of 4'- (aryl methylene) at room temperature after mixingHPyrazoles -5 (4H) -one), the solids crude silica gel filtered out can be recycled after drying after being washed with appropriate solvent.The method of the present invention is environmentally friendly.And raw material is easy to get, and reaction condition is mild, and experimental implementation is simple, and universality is strong, and product postprocessing is convenient, and the thick silica gel of additive can be recycled after simple process, and product yield high.
Description
Technical field
The invention belongs to field of heterocyclic compound in organic chemistry, are related to a kind of preparation method of e derivatives.It is special
It is not a kind of preparation method of 4,4'- (aryl methylene) bis- (- 5 (4H) -one of 1- aryl -3- Trifluoromethyl-1 H- pyrazoles)
Background technique
Nowadays, e derivatives had attracted more and more attention from people due to other various drugs, bioactivity and
Research.Pyrazolone compound may be used as antitumor, cell factor inhibitors, biological enzyme inhibitor etc..Contain two
The compound of a pyrazoles ketone heterocyclic has antibacterial, antiviral, anti-inflammatory, antidepressant activity, and in addition it is also used as certain gold
Belong to the extractant or ligand of ion.At present
Document one: the 4,4'-'s (aryl methylene) of report bis- (- 5 (4H) -one of 1- aryl -3- Trifluoromethyl-1 H- pyrazoles)
Synthetic method, as shown in Scheme 1: with 1- aryl -3- trifluoromethyl -5- pyrazolone (1) and aromatic aldehyde (2) for raw material.By 1-
Aryl -3- trifluoromethyl -5- pyrazolone, aromatic aldehyde and NH4Mortar is added simultaneously in OAc, at room temperature griding reaction, condensation
Obtain 4,4'- (aryl methylene) bis- (- 5 (4H) -one of 1- aryl -3- Trifluoromethyl-1 H- pyrazoles) (3).
It is had the disadvantage that with the method synthesis that document one provides:
The method additive therefor of offer is ammonium acetate.Ammonium acetate is a kind of white triangles crystal for having acetic acid odor, right
Body has certain harm, stimulates skin, mucous membrane, eyes, nasal cavity, throat, damages eyes；High concentration stimulates lung, can lead to lung
Ponding.In addition, ammonium acetate easily deliquesces in air, weigh when reaction feeds intake slightly cumbersome, more likely brings moisture into
In reaction system, the progress of reaction is influenced.The most key, the dosage of ammonium acetate is larger (at least monovalent), and reaction terminates
Ammonium acetate cannot recycle afterwards, less desirable from the point of view of economizing on resources.
Document two: the 4,4'-'s (aryl methylene) of report bis- (- 5 (4H) -one of 1- aryl -3- Trifluoromethyl-1 H- pyrazoles)
Synthetic method, as shown in Scheme 2: under the conditions of 1- aryl -3- trifluoromethyl -5- pyrazolone and aromatic aldehyde in water 90 DEG C
Stir a few hours, the bis- (1- aryl -3- Trifluoromethyl-1 H- pyrazoles -5 of the available 4,4'- of cooled and filtered (aryl methylene)
(4H) -one).
It is had the disadvantage that with the method synthesis that document two provides:
Firstly, the method provided is reacted under the conditions of needing to be heated to 90 DEG C, hot conditions reaction needs to consume many energy
Amount, from the point of view of energy conservation and environmental protection, although the water for having used green is solvent, inevitably energy consumption problem.
Secondly, the reaction time is long, and Shi Changwei 6~8 hours, the low efficiency in comparison reacted.
Third, the bis- (1- aryl -3- Trifluoromethyl-1 H- pyrazoles -5 of 4,4'- (aryl methylene) of the method preparation provided
(4H) -one) compound yield be 70%~89%, be not optimal conversion ratio, do not promote the preferably conversion of raw material.
Document three: the 4,4'-'s (aryl methylene) of report bis- (- 5 (4H) -one of 1- aryl -3- Trifluoromethyl-1 H- pyrazoles)
Synthetic route is as shown in Scheme 3: 1- aryl -3- trifluoromethyl -5- pyrazolone and aromatic aldehyde being mixed, in N2Protection is lower to be added
To 120 DEG C~130 DEG C, stirring is cooled to room temperature heat after 15 minutes, and appropriate ethyl acetate and petroleum ether is added as mixed solvent
It flows back again 15 minutes, it is rear to be cooled to room temperature again, there is solid precipitation, wash solid with solvent after filtering, solid drying can obtain 4,4'-
(aryl methylene) bis- (- 5 (4H) -one of 1- aryl -3- Trifluoromethyl-1 H- pyrazoles) target products.
It is had the disadvantage that with the method synthesis that document three provides:
Firstly, the synthetic method needs provided are carried out in two steps, process is cumbersome, complicated for operation.
Secondly, the method first step needs provided carry out under the conditions of nitrogen protection, condition is harsh, compares environmental requirement
It is high.
Third, the method provided need to use petroleum ether and ethyl acetate as reaction dissolvent, be not meet very much it is environmentally protective
Requirement.4th, although the reaction time shortens, reaction process needs secondary temperature elevation-cooling procedure, increases disappearing for energy
Consumption.
Solvent free reaction, also referred to as solvent-free reaction, exactly carry out reactant without using conventional solvent itself is anti-
It answers, the generation of reaction originates from the diffusion contact of two reactant molecules, then reacts, and generates product molecule comprising
Classical solid-solid reaction further includes solid-liquid reaction and solid-gas reaction.Solvent-free reaction meets the theory of Green Chemistry.Green
Chemistry is desirable with the principles of chemistry and method is reduced or eliminated to human health, the harmful chemical reaction solvent of environment etc., and nothing
Solvation energy avoids not only reducing pollution using a large amount of toxics and volatile organic compounds, simplify operation and
Last handling process shortens the reaction time, reduces production cost, and have many advantages, such as that high income, selectivity are strong toward contact,
Therefore solvent-free reaction is an important channel for realizing Green Chemistry.The reaction of reported solvent free main method [2]
There are several types of: polishing, phase transfer catalysis process, host-guest inclusion method, microwave method, supercritical ultrasonics technology.
Summary of the invention
The purpose of the present invention is to provide a kind of preparation methods of e derivatives.
In order to achieve the above objectives, the present invention uses following reaction mechanism:
In order to achieve the above objectives, the present invention adopts the following technical scheme:
A kind of preparation method of e derivatives, it is characterised in that the specific steps of this method are as follows: by 1- aryl -3- three
Methyl fluoride -5- pyrazolone and substituted aroma aldehyde are dissolved in organic solvent by the molar ratio of 2.0~2.5:1.0~1.2, and reagent is added
The thick silica gel of grade, the dosage of the thick silica gel of the SILVER REAGENT are as follows: every mM of reactant uses thick silica gel 5-10g；After mixing
Solvent is removed, is stirred at room temperature and is ground to fully reacting, with organic solvent washing mixture, is filtered to remove silica gel, solvent is removed and obtains
To crude product, crude product crystalline substance purifies to obtain net product compound 4, the bis- (1- aryl -3- Trifluoromethyl-1 H- pyrroles of 4'- (aryl methylene)
Azoles -5 (4H) -one), structural formula are as follows:
Wherein, Ar are as follows: hydrogen, halogen, C1-C4 alkane methyl, C1-C4 alkoxy, nitro or cyano substituted-phenyl；R are as follows:
Hydrogen, phenyl or p-methylphenyl；The structural formula of the 1- aryl -3- trifluoromethyl -5- pyrazolone are as follows:It is described
Substituted aroma aldehyde structural formula are as follows: Ar-CHO.
The partial size of the thick silica gel of above-mentioned SILVER REAGENT are as follows: 100~200 mesh.
Above-mentioned organic solvent are as follows: ethyl acetate, ethyl alcohol, methylene chloride, chloroform, acetone, benzene, toluene, n-hexane,
The common organic solvent such as petroleum ether.
The method of the present invention with have the reaction time is short, safety is good, environmentally friendly, outstanding yield can be reached, operate
The features such as simplicity, low energy consumption, and post-processing is simple, while the thick silica gel of additive can be recycled after simple process.And raw material
Be easy to get, reaction condition is mild, and experimental implementation is simple, and universality is strong, while the thick silica gel of additive after simple process be recycled make
The features such as using.
Specific embodiment
Embodiment one: in 25mL round-bottomed flask be added 1- phenyl -3- trifluoromethyl -5- pyrazolone (456.0mg,
2.0mmol), benzaldehyde (106.2mg, 1.0mmol) is dissolved with 5mL ethyl acetate, thick silica gel 7g is added, uses after mixing
Revolving instrument is spin-dried for.It is put into magneton to stir at room temperature 12 minutes under magnetic stirring apparatus effect, spiece is taken to be dissolved with solvent,
The tracking of TLC contact plate, after the reaction was completed, washs mixture with appropriate ethyl acetate, is filtered to remove thick silica gel, filtrate is through being removed under reduced pressure
Solvent obtains crude product, and crude product purifies to obtain net product compound 4, bis- (the 1- aryl-of 4'- (aryl methylene) through ethyl alcohol recrystallization
- 5 (4H) -one of 3- Trifluoromethyl-1 H- pyrazoles) (490.0mg, 90%).
The structure of the compound are as follows:
Molecular formula: C27H19F6N4O2
Chinese name: 4,4'- (benzylidene) bis- (- 5 (4H) -one of 1- phenyl -3- Trifluoromethyl-1 H- pyrazoles)
English name: 4,4'- (phenylmethylene) bis (1-phenyl-3- (trifluoromethyl) -1H-
pyrazol-5(4-H)-one)
Molecular weight: 544.46
Fusing point: 202-204 DEG C
Appearance: white powder
Infrared spectroscopy (KBr pallet, cm-1):3394,3064,2923,2853,1698,1593,1490,1364,
1265,1128,999.
Nuclear magnetic resonance spectroscopy:1H NMR(400MHz,DMSO-d6): δ 5.22 (s, 1H, CH), 7.12 (t, J=6.60Hz,
1H, Ar-H), 7.23-7.29 (m, 6H, Ar-H), 7.40 (t, J=8.00Hz, 4H, Ar-H), 7.87 (d, J=7.60Hz, 4H,
Ar–H)ppm.
Carbon-13 nmr spectra:13C NMR(75MHz,DMSO-d6):δ32.87,95.77,100.60,120.82,124.82,
125.19,127.30,127.57,128.12,139.75,143.94,158.12ppm.
Enantiomeric excess:19F NMR(470MHz,acetone-d6):δ–60.2ppm.
Mass spectrum: HRMS (ESI) m/z:[M+H]+545.1367.
Embodiment two: in 25mL round-bottomed flask be added 1- phenyl -3- trifluoromethyl -5- pyrazolone (456.0mg,
2.0mmol), 4- nitrobenzaldehyde (152.2mg, 1.0mmol) is dissolved with 5mL ethyl acetate, and thick silica gel 5g is added, and mixing is equal
It is spin-dried for after even with revolving instrument.It is put into magneton in being spin-dried for the mixture that solvent obtains, is stirred at room temperature under magnetic stirring apparatus effect
It mixes 10 minutes, spiece is taken to be dissolved with solvent, the tracking of TLC contact plate after the reaction was completed, washs mixing with appropriate ethyl acetate
Object is filtered to remove thick silica gel, and filtrate is removed under reduced pressure solvent and obtains crude product, and crude product purifies to obtain net product through ethyl alcohol recrystallization
Compound 4,4'- (4- nitro benzylidene) bis- (- 5 (4H) -one of 1- phenyl -3- Trifluoromethyl-1 H- pyrazoles) (552.4mg,
97%).
The structure of the compound are as follows:
Molecular formula: C27H18F6N5O4
Chinese name: 4,4'- (p-nitrophenyl methylene) bis- (- 5 (4H) -one of 1- phenyl -3- Trifluoromethyl-1 H- pyrazoles)
English name: 4,4'- (4-nitrophenylmethylene) bis (1-phenyl-3-
(trifluoromethyl)-1H-pyrazol-5(4-H)-one)
Molecular weight: 589.45
Fusing point: 150-152 DEG C
Appearance: white powder
Infrared spectroscopy (KBr pallet, cm-1):3389,1641,1600,1513,1479,1353,1270,1227,
1134,998.
Nuclear magnetic resonance spectroscopy:1H NMR(500MHz,acetone-d6): δ 5.33 (s, 1H, CH), 7.15 (t, J=
7.37Hz, 2H, Ar-H), 7.34 (t, J=8.12Hz, 4H, Ar-H), 7.55 (d, J=8.50Hz, 2H, Ar-H), 7.94 (d, J
=7.74Hz, 4H, Ar-H), 8.06 (d, J=8.69Hz, 2H, Ar-H) ppm.
Carbon-13 nmr spectra:13C NMR(75MHz,DMSO-d6):δ32.97,99.24,120.87,123.36,125.57,
128.19,128.58,139.09,145.77,151.20,157.96ppm.
Enantiomeric excess:19F NMR(470MHz,acetone-d6):δ–60.4ppm.
Mass spectrum: HRMS (ESI) m/z:[M+H]+590.1218.
Embodiment three: in 25ml round-bottomed flask be added 1- phenyl -3- trifluoromethyl -5- pyrazolone (456.0mg,
2.0mmol), 4-methoxybenzaldehyde (163.4mg, 1.2mmol) is dissolved with 5mL ethyl acetate, thick silica gel 10g is added, and is mixed
Solvent is spin-dried for revolving instrument after uniformly.It is spin-dried for being put into magneton in the mixture that solvent obtains, be acted in magnetic stirring apparatus in room temperature
Lower stirring 15 minutes, takes spiece to be dissolved with solvent, and the tracking of TLC contact plate after the reaction was completed, is washed with appropriate ethyl acetate
Mixture is filtered to remove thick silica gel, and filtrate is removed under reduced pressure solvent and obtains crude product, and crude product purifies pure through ethyl alcohol recrystallization
Product compound 4,4'- (4- is to methoxybenzylidene) bis- (- 5 (4H) -one of 1- phenyl -3- Trifluoromethyl-1 H- pyrazoles)
(506.8mg, 89%).
The structure of the compound are as follows:
Molecular formula: C28H21F6N4O3
Chinese name: the bis- (1- phenyl -3- Trifluoromethyl-1 H- pyrazoles -5 (4H)-of 4,4'- (4- methoxybenzylidene)
Ketone)
English name: 4,4'- (4-nitrophenylmethylene) bis (1-phenyl-3-
(trifluoromethyl)-1H-pyrazol-5(4-H)-one)
Fusing point: greater than 250 DEG C
Molecular weight: 574.48
Appearance: white powder
Infrared spectroscopy (KBr pallet, cm-1):3426,2930,1602,1484,1373,1273,1133,998.
Nuclear magnetic resonance spectroscopy:1H NMR(500MHz,CDCl3):δ3.71(s,3H,OCH3),5.19(s,1H,CH),6.70
(d, J=8.50Hz, 2H, Ar-H), 7.13 (t, J=7.37Hz, 2H, Ar-H), 7.23 (d, J=8.50Hz, 2H, Ar-H),
7.33 (t, J=7.93Hz, 4H, Ar-H), 7.94 (d, J=7.93Hz, 4H, Ar-H) ppm.
Carbon-13 nmr spectra:13C NMR(75MHz,DMSO-d6):δ31.81,54.51,95.54,100.63,112.77,
120.77,120.58,124.58,127.91,127.97,135.79,139.53,156.94,157.85ppm.
Enantiomeric excess:19F NMR(470MHz,CDCl3):δ–60.4ppm.
Mass spectrum: MS (ESI) m/z:[M+H]+575.1473.
Example IV: in 25mL round-bottomed flask be added 1- phenyl -3- trifluoromethyl -5- pyrazolone (456.0mg,
2.0mmol), 4- chlorobenzaldehyde (140.6mg, 1.0mmol) is dissolved with 5mL ethyl acetate, thick silica gel 5g is added, and is uniformly mixed
Solvent is spin-dried for revolving instrument afterwards.It is put into magneton in being spin-dried for the mixture that solvent obtains, under magnetic stirring apparatus effect at room temperature
Stirring 10 minutes, takes spiece to be dissolved with solvent, the tracking of TLC contact plate, after the reaction was completed, is washed with appropriate ethyl acetate mixed
Object is closed, is filtered to remove thick silica gel, filtrate is removed under reduced pressure solvent and obtains crude product, and crude product purifies to obtain pure production through ethyl alcohol recrystallization
Product compound 4,4'- (4- fluorobenzylidene) bis- (- 5 (4H) -one of 1- phenyl -3- Trifluoromethyl-1 H- pyrazoles) (563.3mg,
97%).
The structure of the compound are as follows:
Molecular formula: C27H18ClF6N4O2
Chinese name: 4,4'- (the chloro- benzylidene of 4-) bis- (- 5 (4H) -one of 1- phenyl -3- Trifluoromethyl-1 H- pyrazoles)
English name: 4,4'- (4-chlorophenylmethylene) bis (1-phenyl-3-
(trifluoromethyl)-1H-pyrazol-5(4-H)-one)
Fusing point: 146-148 DEG C
Molecular weight: 578.90
Appearance: white powder
Infrared spectroscopy (KBr pallet, cm-1):3408,2929,1700,1600,1489,1375,1259,1136,998.
Nuclear magnetic resonance spectroscopy:1H NMR(500MHz,DMSO-d6):δ5.23(s,1H,CH),7.12–7.17(m,4H,Ar–
), H 7.27-7.36 (m, 6H, Ar-H), 7.94 (d, J=8.56Hz, 4H, Ar-H) ppm.
Carbon-13 nmr spectra:13C NMR(75MHz,DMSO-d6):δ32.17,95.50,99.93,120.67,124.97,
127.51,128.15,128.76,130.27,139.33,142.40,157.84ppm.
Enantiomeric excess:19F NMR(470MHz,CDCl3):δ–60.0ppm.
Mass spectrum: HRMS (ESI) m/z:[M+H]+579.1006。
Claims (3)
1. a kind of preparation method of e derivatives, it is characterised in that the specific steps of this method are as follows: by 1- aryl -3- trifluoro
Methyl-5-pyrazolone and substituted aroma aldehyde are dissolved in organic solvent by the molar ratio of 2.0~2.5:1.0~1.2, and SILVER REAGENT is added
Thick silica gel, the dosage of the thick silica gel of the SILVER REAGENT are as follows: every mM of reactant uses thick silica gel 5-10g；It goes after mixing
It except solvent, is stirred at room temperature and is ground to fully reacting, with organic solvent washing mixture, be filtered to remove silica gel, remove solvent and obtain
Crude product, crude product crystalline substance purify to obtain net product compound 4, the bis- (1- aryl -3- Trifluoromethyl-1 H- pyrazoles-of 4'- (aryl methylene)
5 (4H) -one), structural formula are as follows:
Wherein, Ar are as follows: hydrogen, halogen, C1-C4 alkane methyl, C1-C4 alkoxy, nitro or cyano substituted-phenyl；R are as follows: hydrogen, benzene
Base or p-methylphenyl；The structural formula of the 1- aryl -3- trifluoromethyl -5- pyrazolone are as follows:The substitution
The structural formula of aromatic aldehyde are as follows: Ar-CHO.
2. according to the method described in claim 1, it is characterized in that the partial size of the thick silica gel of the SILVER REAGENT are as follows: 100~200
Mesh.
3. according to the method described in claim 1, it is characterized in that the organic solvent are as follows: ethyl acetate, ethyl alcohol, dichloromethane
Alkane, chloroform, acetone, benzene, toluene, n-hexane or petroleum ether.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112070107A (en) * | 2020-07-15 | 2020-12-11 | 上海大学 | Electronic port ship harboring control method |
| WO2024024760A1 (en) * | 2022-07-25 | 2024-02-01 | 公益財団法人野口研究所 | Pyrazolone compound and pyrazolone agent |
-
2019
- 2019-05-13 CN CN201910392049.9A patent/CN110128345A/en active Pending
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112070107A (en) * | 2020-07-15 | 2020-12-11 | 上海大学 | Electronic port ship harboring control method |
| WO2024024760A1 (en) * | 2022-07-25 | 2024-02-01 | 公益財団法人野口研究所 | Pyrazolone compound and pyrazolone agent |
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Application publication date: 20190816 |