CN108191736A - A kind of 2,3- disubstituted indoles analog derivative and preparation method thereof - Google Patents
A kind of 2,3- disubstituted indoles analog derivative and preparation method thereof Download PDFInfo
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- CN108191736A CN108191736A CN201810283733.9A CN201810283733A CN108191736A CN 108191736 A CN108191736 A CN 108191736A CN 201810283733 A CN201810283733 A CN 201810283733A CN 108191736 A CN108191736 A CN 108191736A
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
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Abstract
A kind of 2,3 disubstituted indole analog derivatives.This 2,3 disubstituted indole analog derivative has extensive bioactivity, can be widely applied for lightization, agricultural, medicine and other fields.In addition the invention further relates to a kind of preparation methods of 2,3 disubstituted indole analog derivative.The preparation method constructs 2,3 disubstituted indole class compounds with the alkynyl aniline of different structure and substituted phenyl-bromide by the cascade reaction of palladium chtalyst, easy, efficient, environmentally protective.
Description
Technical field
The present invention relates to a kind of indole derivatives field, and more particularly to one kind 2,3- disubstituted indoles analog derivative and
Preparation method.
Background technology
Indole ring is aromatic heterocycle organic compound, is that one of most wide heterocyclic compound is distributed in nature, extensive
Applied to lightization, pesticide, medicine and other fields.Indoles have similar to flower fragrance, be many fragrance of a flower component part, such as orange
Flower, indoles are also used to manufacture perfume.Indoles and its derivative not only have extensive bioactivity, and extend and be applied to resist
Tumor area, such as anti-inflammatory drug indocin, vasodilator drug pindolol.The indole ring structures of functional modification, can generate and be
The compound of row biology, medicinal activity, this causes indole ring analog derivative to play more and more important work in the exploitation of drug
With.
The preparation of indole ring analog derivative is obtained mostly by classical or basic organic reaction, mainly by transition metal
It is catalyzed the framework that indoles ring skeleton is realized by way of carbon-to-carbon or carbon-to-nitrogen coupling.In existing indole ring analog derivative system
Often with following shortcoming in Preparation Method, raw material sources are relatively expensive, need two kinds or more catalyst joint catalysis, and reaction need to add
Add various ligands or additive, the reaction time is long, and reaction substrate is not easy to prepare, and reaction step is long, and by-product is excessively not easy
It isolates and purifies, reaction yield is not high, and the structure of product is not easy to expand, and atom economy type degree is not high, even with certain
Dangerous nitrine raw material etc..
Therefore, high efficiency, yield are high, have preparation of the green synthesis method of Atom economy in indole ring analog derivative
Become a new guiding in research.
Invention content
The purpose of the present invention is to provide one kind 2,3- disubstituted indole analog derivatives, structure is more easy to extend, have wide
Application prospect.
Another object of the present invention is to provide the preparation method of one kind 2,3- disubstituted indole analog derivatives, this preparation side
Method is easy, green, has Atom economy.
The present invention is solved its technical problem and is realized using following technical scheme.
The present invention proposes one kind 2,3- disubstituted indole analog derivatives, and general structure is as follows：
Wherein R1For straight chained alkyl, branched alkyl or arene group；R2For hydrogen atom, straight chained alkyl, branched alkyl,
Halogen atom, alkoxy, ester group, carbonyl or aldehyde radical；R2It can be at any position of phenyl ring.
The present invention propose one kind 2,3- disubstituted indole analog derivatives preparation method, with the alkynyl aniline of different structure with
Substituted phenyl-bromide constructs the 2,3- disubstituted indoles class compound by the cascade reaction of palladium chtalyst.
The advantageous effect of the embodiment of the present invention is：
A kind of 2,3- disubstituted indoles analog derivative provided by the invention, can be extensive with extensive bioactivity
Applied to the indole ring structures of lightization, agricultural, medicine and other fields, particularly functional modification, it is living that series of biologic, medicine can be generated
The compound of property.
A kind of preparation method of 2,3- disubstituted indoles analog derivative provided by the invention, provides a kind of completely new synthesis
Method generates a series of 2,3- disubstituted indoles derivatives.Product precursor is the alkynyl aniline easily prepared, is cyclized by palladium chtalyst
Reaction, one-step method realizes carbon-to-carbon and carbon-nitrogen bond coupling, and obtains higher yield.The compounding design embodies greenization
Theory, under conditions of more mildly, the target product for obtaining being easily isolated purifying of high yield, the reaction is to precursor
Closing all kinds of modification groups in object has highly compatible so that product structure is easy to modify.The preparation method is indoles ring skeleton
Structure provides a kind of new thinking and strategy.Also, preparation method provided by the invention is easy, efficient, environmentally protective, is changing
To also more wide purposes prospect be shown in being studied in work production, clinical medicine.
Description of the drawings
It in order to illustrate the technical solution of the embodiments of the present invention more clearly, below will be to needed in the embodiment attached
Figure is briefly described, it should be understood that the following drawings illustrates only certain embodiments of the present invention, therefore is not construed as pair
The restriction of range, for those of ordinary skill in the art, without creative efforts, can also be according to this
A little attached drawings obtain other relevant attached drawings.
Fig. 1 is the nuclear magnetic resonance spectroscopy of 2,3- disubstituted indole derivatives prepared by the embodiment of the present invention 1；
Fig. 2 is the carbon-13 nmr spectra of 2,3- disubstituted indole derivatives prepared by the embodiment of the present invention 1；
Fig. 3 is the nuclear magnetic resonance spectroscopy of 2,3- disubstituted indole derivatives prepared by the embodiment of the present invention 2；
Fig. 4 is the carbon-13 nmr spectra of 2,3- disubstituted indole derivatives prepared by the embodiment of the present invention 2.
Specific embodiment
Purpose, technical scheme and advantage to make the embodiment of the present invention are clearer, below will be in the embodiment of the present invention
Technical solution be clearly and completely described.The person that is not specified actual conditions in embodiment, builds according to normal condition or manufacturer
The condition of view carries out.Reagents or instruments used without specified manufacturer is the conventional production that can be obtained by commercially available purchase
Product.
2,3- disubstituted indole analog derivatives of the embodiment of the present invention and preparation method thereof are specifically described below.
The present invention proposes one kind 2,3- disubstituted indole analog derivatives, and general structure is as follows：
Wherein R1For straight chained alkyl, branched alkyl or arene group；R2For hydrogen atom, straight chained alkyl, branched alkyl,
Halogen atom, alkoxy, ester group, carbonyl or aldehyde radical；R2It can be at any position of phenyl ring.
Further, in present pre-ferred embodiments, R1For p-methylphenyl, R2For itrile group, structural formula is formula I；R1For
Normal-butyl, R2For acetyl group, structural formula is formula II：
The present invention proposes the preparation method of one kind 2,3- disubstituted indole analog derivatives, including：With the alkynes of different structure
Base aniline and substituted phenyl-bromide construct 2,3- disubstituted indole class compounds by the cascade reaction of palladium chtalyst.
Further, in present pre-ferred embodiments, a kind of 2,3- disubstituted indoles analog derivative provided by the invention
Preparation method, include the following steps：
A, precursor compound synthesizes；
B, target product synthesizes；
C, it purifies.
Wherein, step a, b synthetic routes are as follows：
Step a includes the following steps：In anhydrous and oxygen-free system, adjacent alkynyl aniline and trifluoroacetic acid are added to four chlorinations
In carbon solvent, addition triphenyl phosphorus is catalyst, and adds a certain amount of triethylamine, stirs 10 minutes in ice water bath environment, so
After be heated to reflux 3 hours, stop reaction, add water washing, extraction, drying, column chromatography, obtain precursor compound.
Wherein, the molar ratio of adjacent alkynyl aniline and trifluoroacetic acid is 1:(0.8-1.0)；Adjacent alkynyl aniline and triphenyl phosphorus
Molar ratio is 1:(2.0-3.0)；Adjacent alkynyl aniline is 1 with triethylamine molar ratio:(1.0-1.2).
Further, in present pre-ferred embodiments, adjacent alkynyl aniline, trifluoroacetic acid, triphenylphosphine and triethylamine exist
Concentration in carbon tetrachloride solvent respectively is 0.1-0.5mol/L, 0.08-0.5mol/L, 0.2-1.5mol/L and 0.1-
0.6mol/L。
Further, in present pre-ferred embodiments, after obtaining precursor compound after reaction, to obtained precursor chemical combination
Object carries out separating-purifying, and first precursor compound is washed with water repeatedly, after concentration then is extracted with ethyl acetate, then with anhydrous sulphur
Sour magnesium drying is finally 1 with volume ratio：The ethyl acetate of (40-80) and the mixed liquor of petroleum ether carry out column chromatography for eluant, eluent
It isolates and purifies, the volume ratio of ethyl acetate and petroleum ether is 1 wherein in mixed liquor：60.
R in precursor compound1For straight chained alkyl, branched alkyl or arene group.
Step b includes the following steps：Under inert gas shielding, under conditions of 110-130 DEG C, by precursor compound with taking
For bromobenzene in n,N-Dimethylformamide solvent, a certain amount of palladium, triphenyl phosphorus, triethylamine, reaction 6-12 are added
After hour, the crude product Compound of 2,3- disubstituted indole analog derivatives is obtained.
Wherein, the molar ratio of precursor compound and substituted phenyl-bromide is 1:(1.0-1.2)；Precursor compound and palladium are rubbed
You are than being 1:(0.02-0.06)；Precursor compound is 1 with triphenyl phosphorus molar ratio:(0.04-0.08)；Precursor compound and three
Ethamine molar ratio is 1:(1.0-1.5).
Further, in present pre-ferred embodiments, precursor compound, substituted phenyl-bromide, palladium, triphenyl phosphorus and three
Concentration of the ethamine in N,N-dimethylformamide solvent respectively is 0.1-0.5mol/L, 0.1-0.6mol/L, 2-
60mmol/L, 4-120mmol/L and 0.1-0.75mol/L.
Step c includes the following steps：First the crude product Compound of 2,3- disubstituted indole analog derivatives is washed with water more
It is secondary, after concentration then is extracted with ethyl acetate, then with anhydrous magnesium sulfate dry extract liquor, after filtering, be evaporated with Rotary Evaporators
Solvent in extract liquor is finally purified with the method split of column chromatography, and the eluent of column chromatography is mixed for ethyl acetate and petroleum ether
Liquid is closed, the volume ratio of ethyl acetate and petroleum ether is 1 in mixed liquor:(20-60).
R in obtained crude product Compound1For straight chained alkyl, branched alkyl or arene group；R2For hydrogen atom, directly
Alkyl group, branched alkyl, halogen atom, alkoxy, itrile group, ester group, carbonyl or aldehyde radical.
The feature and performance of the present invention are described in further detail with reference to embodiments.
Embodiment 1
A kind of preparation method of 2,3- disubstituted indoles analog derivative includes the following steps：
A, precursor compound synthesizes：
In anhydrous and oxygen-free system, by 20mmol adjacency pair tolacetylene bases aniline, 20mmol trifluoroacetic acids and 40ml tetrachloros
Change carbon solvent to be added in 100ml reaction bulbs, add 50mmol triphenyl phosphorus and 22mmol triethylamines, stirred in ice water bath environment
It mixes 10 minutes, is then heated to reflux 3 hours, stop reaction, add water washing multiple, after concentration then is extracted with ethyl acetate, use
Anhydrous magnesium sulfate is dried, and is finally 1 with volume ratio：The ethyl acetate of (40-80) and the mixed liquor of petroleum ether are carried out for eluant, eluent
Column chromatographic isolation and purification, the volume ratio of ethyl acetate and petroleum ether is 1 in mixed liquor：60, obtain precursor compound about
16.3mmol。
B, target product synthesizes：
1mmol precursor compounds and 1.1mmol are placed in 10ml straight pipes bromobenzylcyanide, and add in 0.03mmol vinegar
Then sour palladium, 0.06mmol triphenyl phosphorus carry out argon gas protection to reaction vessel, in ar gas environment, by syringe to straight
5mlN, dinethylformamide and 1.1mmol triethylamines are injected separately into shape pipe.120 DEG C are heated to after being stirred at room temperature 15 minutes,
Reaction stops reaction after 8 hours, obtains target product crude product.
C. it purifies：
First the crude product Compound of 2,3- disubstituted indole analog derivatives is washed with water repeatedly, is then extracted with ethyl acetate
After taking concentration, then with anhydrous magnesium sulfate dry extract liquor, after filtering, be evaporated solvent in extract liquor with Rotary Evaporators, finally use
The method split purification of column chromatography, the eluent of column chromatography are ethyl acetate and the mixed liquor of petroleum ether, acetic acid second in mixed liquor
The volume ratio of ester and petroleum ether is 1:(20-60), column chromatography yield are about 87%.
Embodiment 2
A kind of preparation method of 2,3- disubstituted indoles analog derivative includes the following steps：
A, precursor compound synthesizes：
It is in anhydrous and oxygen-free system, 20mmol neighbour's hexin base aniline, 17mmol trifluoroacetic acids and 40ml carbon tetrachloride is molten
Agent is added in 100ml reaction bulbs, adds 50mmol triphenyl phosphorus and 22mmol triethylamines, 10 points are stirred in ice water bath environment
Then clock is heated to reflux 3 hours, stop reaction, add water washing multiple, after concentration then is extracted with ethyl acetate, with anhydrous sulphur
Sour magnesium drying is finally 1 with volume ratio：The ethyl acetate of (40-80) and the mixed liquor of petroleum ether carry out column chromatography for eluant, eluent
It isolates and purifies, the volume ratio of ethyl acetate and petroleum ether is 1 in mixed liquor：60, obtain precursor compound about 16.5mmol.
B, target product synthesizes：
1mmol precursor compounds and 1.1mmol parabromoacetophenones are placed in 10ml straight pipes, and add in 0.03mmol vinegar
Then sour palladium, 0.06mmol triphenyl phosphorus carry out argon gas protection to reaction vessel, in ar gas environment, by syringe to straight
5mlN, dinethylformamide and 1.1mmol triethylamines are injected separately into shape pipe.120 DEG C are heated to after being stirred at room temperature 15 minutes,
Reaction stops reaction after 8 hours, obtains target product crude product.
C. it purifies：
First the crude product Compound of 2,3- disubstituted indole analog derivatives is washed with water repeatedly, is then extracted with ethyl acetate
After taking concentration, then with anhydrous magnesium sulfate dry extract liquor, after filtering, be evaporated solvent in extract liquor with Rotary Evaporators, finally use
The method split purification of column chromatography, the eluent of column chromatography are ethyl acetate and the mixed liquor of petroleum ether, acetic acid second in mixed liquor
The volume ratio of ester and petroleum ether is 1:(20-60), column chromatography yield are about 91%.
The obtained structure of 2,3- disubstituted indole analog derivatives is passed through1H NMR、13C NMR are measured, Fig. 1, Fig. 2,
Fig. 3 and Fig. 4 is the hydrogen spectrum for 2, the 3- disubstituted indole analog derivatives that embodiment 1 and embodiment 2 obtain and carbon spectrum respectively, is analyzed
To data below：
Embodiment 1：
1H NMR(300MHz,CDCl3):δ8.41(s,1H),7.70―7.44(m,6H),7.30―7.17(m,6H),
2.39(s,3H)；
13C NMR(75.5MHz,CDCl3):δ140.8,138.5,136.0,135.8,133.0,132.4,130.5,
129.7,129.0,128.4,128.0,127.8,123.0,121.0,119.6,119.0,112.6,111.4,109.0,21.4。
Embodiment 2：
1H NMR(300MHz,CDCl3):δ8.20(s,1H),8.08―8.05(t,2H),7.67―7.59(m,3H),
7.38―7.35(d,1H),7.22―7.11(m,2H),2.91―2.86(t,2H),2.66(s,3H),1.75―1.65(m,
2H),1.44―1.34(m,2H,),0.93―0.88(t,3H)；
13C NMR(75.5MHz,CDCl3):δ198.2,141.2,137.2,135.4,134.4,129.4,128.8,
127.4,121.9,120.3,118.7,113.4,110.7,32.0,26.7,26.3,22.6,13.9。
It can be obtained according to above-mentioned data analysis, embodiment 1 and embodiment 2 successfully synthesize 2,3- disubstituted indoles class derivative
The chemical formula of 2, the 3- disubstituted indole analog derivatives of object, wherein embodiment 1 synthesis is as follows：
The chemical formula for the 2,3- disubstituted indole analog derivatives that embodiment 2 synthesizes is as follows：
In conclusion 2,3- disubstituted indole analog derivatives of the embodiment of the present invention and preparation method thereof, the present invention is not with
Isostructural alkynyl aniline and substituted phenyl-bromide construct 2,3- disubstituted indole class compounds by the cascade reaction of palladium chtalyst, this is anti-
The shortcomings of route in previous reaction is long, and substrate and reaction condition requirement are harsh, and the extension of substitution functional group is limited should be overcome, it should
Not only substrate synthesis is simple, reagent is relatively cheap for reaction, and divides with high atom economy, the environmentally protective target that obtains
Son, 2, the 3- disubstituted indoles analog derivative being prepared have extensive bioactivity, can be wide in fields such as medicine, lightization
General application.
Embodiments described above is part of the embodiment of the present invention, instead of all the embodiments.The reality of the present invention
The detailed description for applying example is not intended to limit the range of claimed invention, but is merely representative of the selected implementation of the present invention
Example.Based on the embodiments of the present invention, those of ordinary skill in the art are obtained without creative efforts
Every other embodiment, shall fall within the protection scope of the present invention.
Claims (10)
1. one kind 2,3- disubstituted indole analog derivatives, which is characterized in that the structure of 2, the 3- disubstituted indoles analog derivative
General formula is as follows：
Wherein R1For straight chained alkyl, branched alkyl or arene group；R2For hydrogen atom, straight chained alkyl, branched alkyl, halogen
Atom, alkoxy, ester group, carbonyl or aldehyde radical；R2Any position in phenyl ring.
2. 2,3- disubstituted indoles analog derivative according to claim 1, which is characterized in that the R1For p-methylphenyl or
Normal-butyl, the R2For itrile group or acetyl group.
3. a kind of preparation method for manufacturing 2,3- disubstituted indoles analog derivative as claimed in claim 2, which is characterized in that with
The alkynyl aniline and substituted phenyl-bromide of different structure construct the 2,3- disubstituted indoles class chemical combination by the cascade reaction of palladium chtalyst
Object.
4. the preparation method of 2,3- disubstituted indoles analog derivative according to claim 3, which is characterized in that it includes：
Adjacent alkynyl aniline, trifluoroacetic acid are mixed with carbon tetrachloride solvent, addition triphenyl phosphorus is catalyst, and adds a certain amount of three
Ethamine is heated to reflux after stirring, is stopped reaction, is added water washing, extraction, drying, column chromatography, obtain precursor compound；By described in
Precursor compound, substituted phenyl-bromide are mixed with n,N-Dimethylformamide solvent, add a certain amount of palladium, triphenyl phosphorus, three
Ethamine reaction a period of time, obtains the crude product Compound of 2, the 3- disubstituted indoles analog derivative, is made after isolating and purifying
Obtain the pure 2,3- disubstituted indoles analog derivative.
5. the preparation method of 2,3- disubstituted indoles analog derivative according to claim 4, which is characterized in that neighbour's alkynes
The concentration of base aniline, the trifluoroacetic acid, the triphenylphosphine and the triethylamine in the carbon tetrachloride solvent is divided successively
It Wei not 0.1-0.5mol/L, 0.08-0.5mol/L, 0.2-1.5mol/L and 0.1-0.6mol/L.
6. the preparation method of 2,3- disubstituted indoles analog derivative according to claim 4, which is characterized in that the precursor
Compound, the substituted phenyl-bromide, the palladium, the triphenyl phosphorus and the triethylamine are in the N,N-dimethylformamide
Concentration in solvent respectively is 0.1-0.5mol/L, 0.1-0.6mol/L, 2-60mmol/L, 4-120mmol/L and 0.1-
0.75mol/L。
7. the preparation method of 2,3- disubstituted indoles analog derivative according to claim 4, which is characterized in that after reaction
To after the precursor compound, separating-purifying is carried out to the precursor compound, specifically includes and first uses the precursor compound
Water washing is multiple, then after concentration is extracted with ethyl acetate, and is then 1 with volume ratio：The ethyl acetate and petroleum ether of (40-80) is
Eluant, eluent carries out column chromatographic isolation and purification.
8. the preparation method of 2,3- disubstituted indoles analog derivative according to claim 4, which is characterized in that be obtained by the reaction
2, the 3- disubstituted indoles analog derivative crude product Compound, the thick production to 2, the 3- disubstituted indoles analog derivative
Compounds carry out separating-purifying, specifically include the crude product Compound water of 2, the 3- disubstituted indoles analog derivative first
Washing is multiple, then after concentration is extracted with ethyl acetate, and is then 1 with volume ratio：(20-60) and petroleum ether carry out column for eluant, eluent
Chromatography purifies.
9. the preparation method of 2,3- disubstituted indoles analog derivative according to claim 4, which is characterized in that be made described
The environment of precursor compound is anhydrous and oxygen-free system.
10. the preparation method of 2,3- disubstituted indoles analog derivative according to claim 4, which is characterized in that institute is made
The environment of the crude product Compound of 2,3- disubstituted indole analog derivatives is stated as inert gas system, reaction temperature 110-130
℃。
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| CN109851548A (en) * | 2019-02-15 | 2019-06-07 | 大连理工大学 | A kind of preparation method of novel 2,3- disubstituted indole class compound |
| CN109851548B (en) * | 2019-02-15 | 2022-05-17 | 大连理工大学 | Preparation method of 2, 3-disubstituted indole compound |
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