CN105949152A - Benzofuran derivative and preparation method thereof - Google Patents
Benzofuran derivative and preparation method thereof Download PDFInfo
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- CN105949152A CN105949152A CN201610536407.5A CN201610536407A CN105949152A CN 105949152 A CN105949152 A CN 105949152A CN 201610536407 A CN201610536407 A CN 201610536407A CN 105949152 A CN105949152 A CN 105949152A
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Abstract
The invention discloses a benzofuran derivative and a preparation method thereof. A benzofuran compound is prepared from different multi-alkyne substrates by a cascade reaction. The reaction overcomes the defects of excessively long path, harsh substrate and reaction condition requirements, limited expansion of substituted functional groups and the like in a conventional reaction; the reaction not only is simple in substrate synthesis and relatively low in price of reagents, but also has high atom economy, obtains target molecules in a green and environmental-friendly manner, and provides a valuable approach for industrial production of benzofuran.
Description
Technical field
The invention belongs to organic compound field, be specifically related to a kind of benzofuran derivative and preparation method thereof.
Background technology
Benzofuran compounds has the strongest biological activity, can find the trace of this compounds in substantial amounts of natural and unnatural products.Just
Due to benzofuran compounds and derivant thereof pharmacologically active widely and the generally existence in nature, this compounds causes the close pass of people
Note.
Natural benzofuran compound 1, because it has 2-aryl this kind of structural framework of substituted benzofuran, is demonstrated by good biological activity and such as has guarantor
Protecting ischemic tissue Reperfu-sion, inhibition thrombosis and anti-platelet aggregation etc. act on, this compound by occupy in terms of the treatment of the diseases such as cardiovascular a seat it
Ground.Scammells etc. are with it as lead compound, and design has synthesized a series of analog 2-4, and confirms after testing, and wherein most compound has bright
The aobvious gland robust and sturdy resistant activity of former times A1 receptor.
Many novel and there is the natural benzofuran compound of obvious biological activity be the most constantly found and report, it is expected to be applied to doctor in the future
Medicine field.Hak-Ju Lee in 2008 et al. separation and Extraction from Benzoinum plant goes out the novel native compound 5 having no report, has potential anti-
Bacterium and antifungal activity.
2009, Ramsden etc. reported the benzofuran derivative of a class band sulfo group, and this compounds has regulation histamine receptor, prevention
And treat the panimmunity and inflammatory reaction caused because of histamine receptor mediation, treatment is such as allergy, asthma and autoimmune disease etc..This analog derivative
Structure following 6.
Show good biological activity just because of the most natural benzofuran compounds, but natural product contains the benzene of multiple substituent groups
And kind compound content of muttering is less, the limited amount of separation and Extraction, its yield can not meet people's needs at all.Therefore, synthetic is containing many
The benzofuran compounds of individual substituent group is particularly important especially.
Summary of the invention
For solving above-mentioned technical problem, the invention provides a kind of benzofuran derivative, have multi-ring existence, structure is more complicated, has wide
Application prospect.
Present invention also offers the preparation method of a kind of benzofuran derivative, easy, green, atom economy.
The technical scheme that the present invention takes is:
A kind of benzofuran derivative, the general structure of described benzofuran derivative is as follows:
Wherein, R is straight chained alkyl, branched alkyl, saturated hydrocarbons, unsaturated hydro carbons or arene group；
R1For halogen, straight chained alkyl, branched alkyl, ester group, alkoxyl and its corresponding derivant；R1Can be at the optional position of phenyl ring.
Further, R is preferably isopropyl or ethyl；R1 is preferably chlorine, methyl or ethyl.
Present invention also offers the preparation method of a kind of benzofuran derivative, described preparation method comprises the following steps:
(1) with sodium hydride as catalyst, by malonate and propargyl bromide in anhydrous acetonitrile solvent, ice-water bath reacts 5～8 hours, separate
Obtain compound a after purification；
The formula of described malonate is:
(2) under the conditions of anhydrous and oxygen-free, the substituent of compound a step (1) obtained and phenyl-bromide acetylene is at catalyst and the work of organic base
Under with, in anhydrous acetonitrile solvent 20～35 DEG C react 10～14 hours, isolated and purified after, obtain compound b；
The chemical structural formula of the substituent of described phenyl-bromide acetylene is:
(3) under oxygen is protected, compound b step (2) obtained and diphenyl cyclopropenone are in anhydrous acetonitrile solvent, and 95-100 DEG C anti-
Answer 12～16 hours, isolated and purified after can be prepared by benzofuran derivative.
In described step (1), the ratio of the amount of the material between malonate, propargyl bromide and sodium hydride is 1:2.2～3.2:4～5, malonate
Concentration in anhydrous acetonitrile is 0.8～1.5mol/L.
In described step (2), catalyst is Pd (PPh3)2Cl2With the mixture of CuI, organic base is triethylamine.Pd(PPh3)2Cl2With CuI it
Between the ratio of amount of material be 3:1.
In described step (2), compound a, the substituent of phenyl-bromide acetylene, the ratio of amount of material between catalyst and organic base are 1:2.2～3.2:
0.03～0.05:4～5, compound a concentration in anhydrous acetonitrile is 0.5～0.8mol/L.The isolation and purification method that described step (2) is taked is:
By crude product ethyl acetate and water extract and separate, after concentration, the ethyl acetate with volume ratio is 1:40～60: petroleum ether is that eluant carries out post
Chromatography purification.
In described step (3), the ratio of the amount of the material between compound b and diphenyl cyclopropenone is 1.0～1.5:1；Compound b is anhydrous
Concentration in acetonitrile is 0.1～0.3mol/L.The isolation and purification method that described step (3) is taked is: by crude product ethyl acetate and water extract and separate,
After concentration, the ethyl acetate with volume ratio is 1:20～40: petroleum ether is that eluant carries out column chromatographic isolation and purification.
Compared with prior art, the invention provides a series of new benzofuran derivative.Cascade reaction is passed through with different multiple alkynes substrates
Constructing benzofuran compounds, it is long that this reaction overcomes route in reaction in the past, and substrate and reaction condition require harshness, the extension of replacement functional group
The shortcoming such as limited, the synthesis of this reaction not only substrate is simple, reagent is relatively cheap, and have atom economy, environmental protection obtain target
Molecule, provides a kind of of great value approach to the industrialized production of benzofuran.
Relative to common benzofuran derivative, benzofuran derivative prepared by the present invention has multi-ring existence, and its structure is the most complicated various,
Also more wide purposes prospect will be shown in Chemical Manufacture, clinical medicine.Further, the preparation method that the present invention provides is easy, efficient, instead
Between Ying Shi short, efficiency is high.
Accompanying drawing explanation
Fig. 1 is the general structure of benzofuran derivative；
Fig. 2 is the synthetic route chart of benzofuran derivative；
Fig. 3 is the synthetic route chart of the benzofuran derivative c-1 of embodiment 1 preparation；
Fig. 4 is the proton nmr spectra of the benzofuran derivative c-1 of embodiment 1 preparation；
Fig. 5 is the carbon-13 nmr spectra of the benzofurans ether derivant c-1 of embodiment 1 preparation；
Fig. 6 is the XRD single crystal diffraction figure of the benzofuran derivative c-1 of embodiment 1 preparation；
Fig. 7 is the synthetic route chart of the benzofuran derivative c-2 of embodiment 2 preparation；
Fig. 8 is the proton nmr spectra of the benzofuran derivative c-2 of embodiment 2 preparation；
Fig. 9 is the carbon-13 nmr spectra of the benzofurans ether derivant c-2 of embodiment 2 preparation；
Figure 10 is the synthetic route chart of the benzofuran derivative c-3 of embodiment 3 preparation；
Figure 11 is the proton nmr spectra of the benzofuran derivative c-3 of embodiment 3 preparation；
Figure 12 is the carbon-13 nmr spectra of the benzofurans ether derivant c-3 of embodiment 3 preparation.
Detailed description of the invention
Embodiment 1
A kind of benzofurans analog derivative, described benzofuran derivatives structural formula is:
A kind of preparation method of benzofuran derivative, described preparation method comprises the following steps:
(1) with 830mmol sodium hydride as catalyst, 200mmol Diisopropyl malonate and 440mmol propargyl bromide are joined 210mL
Ice-water bath in anhydrous acetonitrile, stirring reaction 8 hours, product adds water washing, is extracted with ethyl acetate, and decompression is spin-dried for, and obtains brown solid product,
I.e. compound a-1；
(2) 80mmol compound a-1 and 200mmol phenylacetylene bromide are blended in Pd (PPh3)2Cl2In the anhydrous and oxygen-free catalyst system and catalyzing of/CuI
(2.56mmol/0.85mmol), mol ratio Pd (PPh3)2Cl2: CuI=3:1, makees alkali with 336mmol triethylamine, with 150mL anhydrous acetonitrile is
Solvent, 20 DEG C are stirred reaction 12 hours, and products in water washs, and is extracted with ethyl acetate, and decompression is spin-dried for, by the acetic acid second that volume ratio is 1:40
Ester: petroleum ether column chromatography for separation, obtains greenish yellow solid product, i.e. compound b-1.
(3) under conditions of 95 DEG C, the 1.2mmol compound b-1 prepared by step (2) is in 12mL anhydrous acetonitrile solvent and oxygen atmosphere
React 16 hours with 1.0mmol diphenyl cyclopropenone, obtain the crude product of compound c-1, i.e. benzofuran derivative；Benzo furan by preparation
Mutter analog derivative crude product with water washing, ethyl acetate extract, decompression is spin-dried for, and uses volume ratio ethyl acetate: petroleum ether=1:20 column chromatography divides
From, obtaining white solid product, i.e. benzofuran derivative c-1, column chromatography productivity is about 70%.
Product structure passes through1H NMR、13C NMR measures, and result is as follows:
1H NMR (300MHz, CDCl3) δ 7.77-7.75 (m, 2H), 7.40-7.34 (m, 6H), 7.23-7.18 (m, 4H), 7.06 (d,
2H), 6.99-6.89 (m, 4H), 5.16-5.11 (m, 2H), 3.99 (s, 2H), 3.88 (s, 2H), 1.33-1.30 (m, 12H).
13C NMR (126MHz, CDCl3) δ 193.53,171.35,154.91,149.70,141.92,137.74,136.51,136.35,
134.51,133.61,132.80,131.81,129.99,129.52,129.13,128.98,128.35,127.99,127.77,127.51,122.48,
122.04,117.19,114.83,94.67,87.81,70.02,60.43,41.70,38.12,21.99.
Embodiment 2
A kind of benzofurans analog derivative, described benzofuran derivatives structural formula is:
A kind of preparation method of benzofuran derivative, described preparation method comprises the following steps:
(1) with 960mmol sodium hydride as catalyst, 200mmol diethyl malonate and 600mmol propargyl bromide are joined 140mL without
Ice-water bath in water-acetonitrile, stirring reaction 5 hours, product adds water washing, is extracted with ethyl acetate, and decompression is spin-dried for, and obtains brown solid product,
I.e. compound a-2；
(2) 80mmol compound a-2 and 240mmol phenylacetylene bromide are blended in Pd (PPh3)2Cl2In the anhydrous and oxygen-free catalyst system and catalyzing of/CuI
(1.92mmol/0.64mmol), mol ratio Pd (PPh3)2Cl2: CuI=3:1, makees alkali with 384mmol triethylamine, with 100mL anhydrous acetonitrile is
Solvent, stirring reaction 14 hours at 25 DEG C, products in water washs, and is extracted with ethyl acetate, and decompression is spin-dried for, and is the acetic acid of 1:50 by volume ratio
Ethyl ester: petroleum ether column chromatography for separation, obtains brown solid, i.e. compound b-2.
(3) under conditions of 95 DEG C, the 1.5mmol compound b-2 prepared by step (2) is in 5mL anhydrous acetonitrile solvent and oxygen atmosphere
React 14 hours with 1.0mmol diphenyl cyclopropenone, obtain the crude product of compound c-2, i.e. benzofuran derivative；Benzo furan by preparation
Mutter analog derivative crude product with water washing, ethyl acetate extract, decompression is spin-dried for, and uses volume ratio ethyl acetate: petroleum ether=1:30 column chromatography divides
From, obtaining white solid product, i.e. benzofuran derivative c-2, column chromatography productivity is about 63%.
Product structure passes through1H NMR、13C NMR measures, and result is as follows:
1H NMR (300MHz, CDCl3) δ 7.93-7.79 (m, 4H), 7.54-7.12 (m, 14H), 4.21-4.14 (m, 4H), 3.83 (t, 2H),
3.46 (t, 2H), 2.82-2.74 (m, 2H), 2.68-2.60 (m, 2H), 1.62-1.53 (m, 3H), 1.38-1.17 (m, 11H).
13C NMR (75MHz, CDCl3) δ 193.11,172.02,157.14,145.07,144.37,139.64,137.97,134.06,132.09,
131.89,130.85,130.44,129.58,128.85,128.24,127.82,126.87,121.10,116.44,96.92,87.37,62.15,
60.07,41.29,40.43,29.26,29.20,15.92,15.79,14.40.
Embodiment 3
A kind of benzofurans analog derivative, described benzofuran derivatives structural formula is:
A kind of preparation method of benzofuran derivative, described preparation method comprises the following steps:
(1) with 900mmol sodium hydride as catalyst, 200mmol Diisopropyl malonate and 500mmol propargyl bromide are joined 160mL
Ice-water bath in anhydrous acetonitrile, stirring reaction 7.5 hours, product adds water washing, is extracted with ethyl acetate, and decompression is spin-dried for, and obtains brown solid product
Thing, i.e. compound a-3；
(2) 80mmol compound a-3 and 224mmol phenylacetylene bromide are blended in Pd (PPh3)2Cl2In the anhydrous and oxygen-free catalyst system and catalyzing of/CuI
(3.84mmol/1.28mmol), mol ratio Pd (PPh3)2Cl2: CuI=3:1, makees alkali with 360mmol triethylamine, with 135mL anhydrous acetonitrile is
Solvent, stirring reaction 10 hours under room temperature, products in water washs, and is extracted with ethyl acetate, and decompression is spin-dried for, and is the acetic acid of 1:60 by volume ratio
Ethyl ester: petroleum ether column chromatography for separation, obtains white solid product, i.e. compound b-3.
(3) under conditions of 100 DEG C, the 1.5mmol compound b-3 prepared by step (2) is in 5mL anhydrous acetonitrile solvent and oxygen atmosphere
React 16 hours with 1.0mmol diphenyl cyclopropenone, obtain the crude product of compound c-3, i.e. benzofuran derivative；Benzo furan by preparation
Mutter analog derivative crude product with water washing, ethyl acetate extract, decompression is spin-dried for, and uses volume ratio ethyl acetate: petroleum ether=1:40 column chromatography divides
From, obtaining white solid product, i.e. benzofuran derivative c-3, column chromatography productivity is about 68%.
Product structure passes through1H NMR、13C NMR measures, and result is as follows:
1H NMR (300MHz, CDCl3) δ 7.78-7.76 (m, 2H), 7.36-7.33 (m, 6H), 7.17-6.99 (m, 9H), 6.77 (s, 1H),
5.18-5.10 (m, 2H), 3.99 (s, 2H), 3.91 (s, 2H), 2.26 (dd, 2H), 2.08 (dd, 2H), 1.33-1.30 (m, 12H).
13C NMR (126MHz, CDCl3) δ 193.21,172.08,154.18,149.26,141.46,137.75,137.50,137.23,
136.76,132.66,131.87,130.93,128.63,128.29,128.05,128.01,127.89,127.43,127.20,127.14123.32,
121.41,117.11,114.67,95.27,86.60,69.51,60.07,41.41,37.73,21.60,21.14.
The above-mentioned detailed description carried out benzofuran derivative and preparation method thereof with reference to embodiment, is illustrative rather than determinate, can
According to restriction scope list several embodiments, therefore changing and modifications under without departing from present general inventive concept, the protection of the present invention should be belonged to
Within the scope of.
Claims (10)
1. a benzofuran derivative, it is characterised in that the general structure of described benzofuran derivative is as follows:
Wherein, R is straight chained alkyl, branched alkyl, saturated hydrocarbons, unsaturated hydro carbons or arene group；
R1For halogen, straight chained alkyl, branched alkyl, ester group, alkoxyl and its corresponding derivant；R1Can be at the optional position of phenyl ring.
Benzofuran derivative the most according to claim 1, it is characterised in that described R is isopropyl or ethyl；R1For chlorine, methyl or ethyl.
The preparation method of benzofuran derivative the most according to claim 1, it is characterised in that described preparation method comprises the following steps:
(1) with sodium hydride as catalyst, by malonate and propargyl bromide in anhydrous acetonitrile solvent, ice-water bath reacts 5～8 hours, separate
Obtain compound a after purification；
The formula of described malonate is:
(2) under the conditions of anhydrous and oxygen-free, the substituent of compound a step (1) obtained and phenyl-bromide acetylene is at catalyst and the work of organic base
Under with, in anhydrous acetonitrile solvent 20～35 DEG C react 10～14 hours, isolated and purified after, obtain compound b；
The chemical structural formula of the substituent of described phenyl-bromide acetylene is:
(3) under oxygen is protected, compound b step (2) obtained and diphenyl cyclopropenone are in anhydrous acetonitrile solvent, and 95-100 DEG C anti-
Answer 12～16 hours, isolated and purified after can be prepared by benzofuran derivative.
Preparation method the most according to claim 3, it is characterised in that in described step (1), between malonate, propargyl bromide and sodium hydride
The ratio of the amount of material is 1:2.2～3.2:4～5, and malonate concentration in anhydrous acetonitrile is 0.8～1.5mol/L.
Preparation method the most according to claim 3, it is characterised in that in described step (2), catalyst is Pd (PPh3)2Cl2With mixing of CuI
Compound, organic base is triethylamine.
Preparation method the most according to claim 5, it is characterised in that Pd (PPh3)2Cl2With the ratio of the amount of the material between CuI is 3:1.
7. according to the preparation method described in claim 3-6 any one, it is characterised in that in described step (2), compound a, phenyl-bromide acetylene
The ratio of the amount of the material between substituent, catalyst and organic base is 1:2.2～3.2:0.03～0.05:4～5, dense in anhydrous acetonitrile of compound a
Degree is 0.5～0.8mol/L.
Preparation method the most according to claim 3, it is characterised in that in described step (3), between compound b and diphenyl cyclopropenone
The ratio of the amount of material is 1.0～1.5:1；Compound b concentration in anhydrous acetonitrile is 0.1～0.3mol/L.
9. according to the preparation method described in claim 3, it is characterised in that the isolation and purification method that described step (2) is taked is: by crude product acetic acid
Ethyl ester and water extract and separate, after concentration, the ethyl acetate with volume ratio is 1:40～60: petroleum ether is that eluant carries out column chromatographic isolation and purification.
10. according to the preparation method described in claim 3, it is characterised in that the isolation and purification method that described step (3) is taked is: by crude product acetic acid
Ethyl ester and water extract and separate, after concentration, the ethyl acetate with volume ratio is 1:20～40: petroleum ether is that eluant carries out column chromatographic isolation and purification.
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| CN107954873A (en) * | 2017-12-07 | 2018-04-24 | 安徽师范大学 | A kind of polysubstituted olefin(e) acid ester derivant and preparation method thereof |
| CN109369508A (en) * | 2018-11-28 | 2019-02-22 | 安徽师范大学 | A kind of polysubstituted indole derivatives and preparation method thereof |
| CN110256491A (en) * | 2019-07-03 | 2019-09-20 | 安徽师范大学 | One kind class ligand of phosphorus oxygen containing triaryl and preparation method thereof |
| CN114605341A (en) * | 2022-04-25 | 2022-06-10 | 安徽师范大学 | Benzisoxazole compound and preparation method thereof |
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| CN106749139A (en) * | 2016-11-29 | 2017-05-31 | 安徽师范大学 | One kind is polysubstituted to condense benzofuran derivative and preparation method thereof |
| CN106749139B (en) * | 2016-11-29 | 2019-03-26 | 安徽师范大学 | Polysubstituted condensed benzofuran derivative of one kind and preparation method thereof |
| CN107954873A (en) * | 2017-12-07 | 2018-04-24 | 安徽师范大学 | A kind of polysubstituted olefin(e) acid ester derivant and preparation method thereof |
| CN107954873B (en) * | 2017-12-07 | 2020-06-19 | 安徽师范大学 | Polysubstituted olefine acid ester derivative and preparation method thereof |
| CN109369508A (en) * | 2018-11-28 | 2019-02-22 | 安徽师范大学 | A kind of polysubstituted indole derivatives and preparation method thereof |
| CN109369508B (en) * | 2018-11-28 | 2021-08-27 | 安徽师范大学 | Polysubstituted indole derivative and preparation method thereof |
| CN110256491A (en) * | 2019-07-03 | 2019-09-20 | 安徽师范大学 | One kind class ligand of phosphorus oxygen containing triaryl and preparation method thereof |
| CN110256491B (en) * | 2019-07-03 | 2021-08-27 | 安徽师范大学 | Triaryl phosphorus oxygen-containing ligand and preparation method thereof |
| CN114605341A (en) * | 2022-04-25 | 2022-06-10 | 安徽师范大学 | Benzisoxazole compound and preparation method thereof |
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