CN109096293A - Preparation method of the one kind containing the benzofuran simultaneously alcohol compound of [2,3-b] pyridine structure - Google Patents
Preparation method of the one kind containing the benzofuran simultaneously alcohol compound of [2,3-b] pyridine structure Download PDFInfo
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- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
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Abstract
The present invention relates to one kind to contain benzofuran simultaneously [2,3-b] pyridine structure alcohol compound preparation method, belong to technical field of organic synthesis, using guaiacol and the fluoro- 6- picoline of 2- as raw material, successively pass through etherification reaction, the alcohol compound of intramolecular cyclization and hydrolysis preparation containing benzofuran simultaneously [2,3-b] pyridine structure.The present invention has the advantages that at low cost, with high purity, reaction yield is high and isomer-free.
Description
Technical field
The present invention relates to a kind of preparation methods containing the benzofuran simultaneously alcohol compound of [2,3-b] pyridine structure, belong to
In technical field of organic synthesis.
Background technique
Electroluminescent refers to luminescent material under electric field action, and the luminous phenomenon by electric current or electric field excitation, is one
A luminescence process that electric energy is converted into luminous energy research and reaches real although it is many to generate electroluminescent substance
The more still inorganic semiconductor material of border application level, but because of the manufacture craft, cost and hair of inorganic semiconductor material
Light efficiency, luminescent color and it is difficult to realize the limitation that large-area flat-plate is shown, promotes to seek preparation process and performance is more preferably sent out
Luminescent material, thus electroluminescent organic material enters research vision.For synthesis, electroluminescent organic material is partly led compared to inorganic
For body material, there is light path range large area photoelectric display achievable greatly, be easy to get to blue light, brightness is big, high-efficient, driving is electric
It forces down, consume energy less and the simple advantage at low cost of manufacture craft, but in the preparation of organic electroluminescence device (OLED) and excellent
In change, the selection of electroluminescent organic material is still most important.
In the selection synthesis of electroluminescent organic material, the alcohols of discovery benzofuran simultaneously [2,3-b] pyridine structure
Closing object is a kind of important photoelectric material intermediate, after generating complex compound with metals coordinations such as iridium, can be applied to organic electroluminescence hair
The organic electronics fields such as luminescent material, organic effect pipe and organic non linear optical material.
Chinese invention patent CN103804426A, it is disclosed to have with the iridium complex with the benzo-fused ligand of azepine-
In the compound of pass, device and composite, the preparation method of benzofuran simultaneously [2,3-b] pyridine -8- alcohol is disclosed, using 2- ammonia
The bromo- 6- picoline of base -3- and 2,3- dimethoxyphenylboronic are raw material, through Suzuki C-C coupling, intramolecular cyclization and are hydrolyzed
To benzofuran, simultaneously [2,3-b] pyridine alcoholic compound, reaction route are as follows:
The market price of raw material 2- amino -3- bromo- 6- picoline and 2,3- methoxyphenylboronic acid used in above-mentioned preparation
Lattice are higher and are not easy to buy, also, last hydrolysis needs to reach 200 DEG C of high temperature, are not suitable for industrialized production, will lead
Final raw material and production cost is caused substantially to increase, it is difficult to meet the requirement that organic light emission sends a telegraph materials industrialization.
Summary of the invention
To solve the above technical deficiency, the present invention provides the alcohol containing benzofuran simultaneously [2,3-b] pyridine structure
The preparation method of class compound, the cost containing the benzofuran simultaneously alcohol compound of [2,3-b] pyridine structure prepared is low,
Purity is high, reaction yield height and isomer-free.
Technical scheme is as follows: one kind containing the benzofuran simultaneously alcohol compound of [2,3-b] pyridine structure
Preparation method includes the following steps,
Step (1) etherification reaction: under the conditions of 80~140 DEG C, connect using guaiacol and the fluoro- 6- picoline of 2- as raw material
It is added in the first solvent with acid-binding agent, 3~12h of reaction obtains etherification product, wherein guaiacol and the fluoro- 6- picoline of 2-
Molar ratio is 1.0~2.0:1；
Step (2) intramolecular cyclization: under the conditions of 120~140 DEG C, the etherification product that step (1) is obtained is together with catalysis
Agent and oxidant are added in the second solvent, react 4~12h, obtain the ethers containing benzofuran simultaneously [2,3-b] pyridine structure
Close object；
Step (3) hydrolysis: under the conditions of 90~110 DEG C, by step (2) obtain containing benzofuran simultaneously [2,3-
B] 4~12h is reacted in 1:2.0~5.0 in molar ratio with 48% hydrobromic acid for the ether compound of pyridine structure, it obtains containing benzo furan
It mutters the alcohol compound of simultaneously [2,3-b] pyridine structure.
Technical solution of the present invention further include: the acid-binding agent in the step (1) is cesium carbonate, in potassium carbonate, sodium carbonate
One or more, the molar ratio of acid-binding agent and the fluoro- 6- picoline of 2- is 1.0~2.0:1, the first solvent is N, N- diformazan
Base formamide.
Technical solution of the present invention further include: the molar ratio of guaiacol and the fluoro- 6- picoline of 2- in the step (1)
For 1:1, reaction temperature is 130 DEG C, reaction time 8h.
Technical solution of the present invention further include: the catalyst in the step (2) is palladium acetate, palladium trifluoroacetate, four (three
Phenylphosphine) palladium, tris(dibenzylideneacetone) dipalladium, one or more of palladium chloride, the molar ratio of catalyst and etherification product
For 0.01~0.2:1.
Technical solution of the present invention further include: the oxidant in the step (2) is silver oxide, in copper acetate, silver acetate
One or more, the molar ratio of oxidant and etherification product is 1~5:1.
Technical solution of the present invention further include: second solvent is one or both of glacial acetic acid, pivalic acid, step
(2) reaction temperature is 130 DEG C, reaction time 8h.
Technical solution of the present invention further include: what 48% hydrobromic acid and step (2) obtained in the step (3) contains benzo
The molar ratio of the furans simultaneously ether compound of [2,3-b] pyridine structure is 4.5:1, and reaction temperature is 105 DEG C, and the reaction time is
8h。
Technical solution of the present invention further include: the etherification product that the step (1) obtains is 2- (2- methoxyphenoxy)-
6- picoline, the extraction process of 2- (2- the methoxyphenoxy) -6- picoline are as follows:
Step (1) after the reaction was completed, is toppled in water and is quenched, be extracted with ethyl acetate later, then with organic phase anhydrous slufuric acid
Sodium is dry, and the rear desolventizing that depressurizes obtains yellow oil, and 2- (2- methoxybenzene oxygen can be obtained with petroleum ether or dehydrated alcohol crystallization
Base) -6- picoline.
Technical solution of the present invention further include: what the step (2) obtained contains benzofuran simultaneously [2,3-b] pyridine structure
Ether compound be 8- methoxyl group -2- methyl benzofuran simultaneously [2,3-b] pyridine, the 8- methoxyl group -2- methyl benzo furan
It mutters the extraction process of simultaneously [2,3-b] pyridine are as follows:
Step (2) after the reaction was completed, is toppled in sodium hydrate aqueous solution, after be extracted with ethyl acetate, then with organic phase without
Aqueous sodium persulfate is dry, depressurizes desolventizing later and obtains sepia grease, and crossing silicagel column can be obtained 8- methoxyl group -2- methyl benzo
Furans simultaneously [2,3-b] pyridine crude product.
Technical solution of the present invention further include: the reactant extraction process of the step (3) are as follows: after completion of the reaction, be added
Water quenching reaction, after be extracted with ethyl acetate, then dry with organic phase anhydrous sodium sulfate, desolventizing obtains brown solid crude product,
Again with toluene ethyl alcohol recrystallization, it is 2- methyl benzofuran simultaneously [2,3-b] pyridine -8- alcohol that 10 DEG C of suction filtrations, which obtain brown solid,.
The beneficial effects of the present invention are: the alcohol compound containing benzofuran simultaneously [2,3-b] pyridine structure prepared
Reaction yield it is high, total recovery can reach 47-55%, and purity is high, HPLC (high performance liquid chromatography) purity up to 99.9%,
List is miscellaneous to be less than 100ppm, and isomer-free, simultaneous reactions step is short, preparation method is simple, raw material is cheap and easy to get, can reduce cost,
Production process is safe and environment-friendly, efficient, can meet the application of the organic photoelectrical materials such as OLED, is suitble to large-scale production.
Detailed description of the invention
Fig. 1 is reaction route schematic diagram of the invention.
Specific embodiment
The invention will be further described by the following examples.
It makes an explanation first to the abbreviation abbreviation during the preparation process using substance:
DMF, English name: N, N-dimethylformamide, Chinese: n,N-Dimethylformamide.
Pd(OAc)2, English name: Palladium acetate, Chinese: palladium acetate, also known as acid chloride.
Pd(TFA)2, English name: Palladium (II) trifluoroacetate, Chinese: palladium trifluoroacetate.
Pd(PPh3)4, English name: Tetrakis (triphenylphosphine) Palladium, Chinese: four
(triphenylphosphine) palladium.
Pd2(dba)3, English name: Tris (dibenzylideneacetone) dipalladium, Chinese: three
(dibenzalacetone) two palladium.
PdCl2, English name: Palladium chloride, Chinese: palladium chloride, also known as palladium chloride.
Ag2O, English name: Silver oxide, Chinese: silver oxide.
Cu(OAc)2, English name: Copper (II) acetate, Chinese: copper acetate.
AgOAc, English name: Silver acetate, Chinese: silver acetate.
Embodiment 1:
Step 1: the preparation of 2- (2- methoxyphenoxy) -6- picoline:
By the fluoro- 6- picoline of 22.2g (0.2mol) 2-, 24.8g (0.2mol) guaiacol and 97.7g (0.3mol) carbon
Sour caesium is added in 200mL DMF solution, is stirred to react in 135~140 DEG C 8 hours, and TLC tracks reaction process.
After completion of the reaction, system is poured into 2000ml water and is quenched, and is extracted with 500g ethyl acetate, organic phase anhydrous slufuric acid
Sodium is dry, and decompression desolventizing obtains yellow oil, is crystallized with petroleum ether/dehydrated alcohol, obtains 39.6g 2- (2- methoxybenzene
Oxygroup) -6- picoline, white crystal, yield 92.0%, GC purity is 99.5%.
Step 2: the preparation of 8- methoxyl group -2- methyl benzofuran simultaneously [2,3-b] pyridine:
By 21.5g (0.1mol) 2- (2- methoxyphenoxy) -6- picoline, 92.7g (0.4mol) silver oxide and
3.0g (0.01mol) palladium trifluoroacetate is added in 200g pivalic acid, and system is stirred to react 8.0 hours in 135~140 DEG C, TLC
Track reaction process.
After completion of the reaction, system pours into 400g sodium hydrate aqueous solution, with 500 ethyl acetate extract, organic phase without
Aqueous sodium persulfate is dry, and decompression desolventizing obtains sepia grease, crosses silicagel column, obtains 8- methoxyl group -2- methyl benzofuran
And [2,3-b] pyridine crude product 17.1g, white crystal, yield 80.2%, GC purity are 99.6%.
Step 3: the preparation of 2- methyl benzofuran simultaneously [2,3-b] pyridine -8- alcohol:
By 21.3g (0.1mol) 8- methoxyl group -2- methyl benzofuran simultaneously [2,3-b] pyridine and 75.8g (0.45mol)
48% hydrobromic acid is added in 500mL three-necked flask, and system is stirred to react 8.0 hours in 100~105 DEG C, TLC tracking react into
Journey.
After completion of the reaction, 50g water quenching reaction is added, is extracted with 500g ethyl acetate, organic phase anhydrous sodium sulfate is dry,
Desolventizing obtains brown solid.Gained crude product uses toluene ethyl alcohol recrystallization, and 10 DEG C of suction filtrations obtain brown solid 14.9g, yield
74.8%, HPLC purity 99.9%, single miscellaneous respectively less than 100ppm.
Compound structure characterization: MS (ESI): 200.16 ([M+1]+), calculated value 199.06.1H NMR(400MHz,
CDCl3) δ: 8.12~8.10 (d, J=7.6Hz, 1H), 7.49~7.47 (dd, J=8Hz, 0.8Hz, 1H), 7.29~7.25
(t, 1H), 7.19~7.17 (d, J=7.6Hz, 1H), 7.02~7.01 (dd, J=8Hz, 0.8Hz, 1H), 5.35 (s, 1H) and
2.68(s,3H)。
Embodiment 2:
Step 1: the preparation of 2- (2- methoxyphenoxy) -6- picoline:
By the fluoro- 6- picoline of 22.2g (0.2mol) 2-, 49.6g (0.4mol) guaiacol and 55.3g (0.4mol) carbon
Sour potassium is added in 200mL DMF solution, is stirred to react in 135~140 DEG C 8 hours, and TLC tracks reaction process.
After completion of the reaction, system is poured into 2000ml water and is quenched, and is extracted with 500g ethyl acetate, organic phase anhydrous slufuric acid
Sodium is dry, and decompression desolventizing obtains yellow oil, is crystallized with petroleum ether/dehydrated alcohol, obtains 37.8g 2- (2- methoxybenzene
Oxygroup) -6- picoline, white crystal, yield 87.9%, GC purity is 99.5%.
Step 2: the preparation of 8- methoxyl group -2- methyl benzofuran simultaneously [2,3-b] pyridine:
By 21.5g (0.1mol) 2- (2- methoxyphenoxy) -6- picoline, 66.8g (0.4mol) silver acetate and
2.2g (0.01mol) palladium acetate is added in 200g glacial acetic acid, and system is stirred to react 8.0 hours in 135~140 DEG C, TLC tracking
Reaction process.
After completion of the reaction, system pours into 400g sodium hydrate aqueous solution, with 500 ethyl acetate extract, organic phase without
Aqueous sodium persulfate is dry, and decompression desolventizing obtains sepia grease, crosses silicagel column, obtains 8- methoxyl group -2- methyl benzofuran
And [2,3-b] pyridine crude product 16.7g, white crystal, yield 78.3%, GC purity 99.6%.
Step 3: the preparation of 2- methyl benzofuran simultaneously [2,3-b] pyridine -8- alcohol:
By 21.3g (0.1mol) 8- methoxyl group -2- methyl benzofuran simultaneously [2,3-b] pyridine and 50.6g (0.3mol)
48% hydrobromic acid is added in 500mL three-necked flask, and system is stirred to react 8.0 hours in 100~105 DEG C, TLC tracking react into
Journey.
After completion of the reaction, 50g water quenching reaction is added, is extracted with 500g ethyl acetate, organic phase anhydrous sodium sulfate is dry,
Desolventizing obtains brown solid.Gained crude product uses toluene ethyl alcohol recrystallization, and 10 DEG C of suction filtrations obtain brown solid 13.7g, yield
68.9%, HPLC purity 99.9%, single miscellaneous respectively less than 100ppm.
Compound structure characterization: MS (ESI): 200.16 ([M+1]+), calculated value 199.06.1H NMR(400MHz,
CDCl3) δ: 8.12~8.10 (d, J=7.6Hz, 1H), 7.49~7.47 (dd, J=8Hz, 0.8Hz, 1H), 7.29~7.25
(t, 1H), 7.19~7.17 (d, J=7.6Hz, 1H), 7.02~7.01 (dd, J=8Hz, 0.8Hz, 1H), 5.35 (s, 1H) and
2.68(s,3H)。
The above is only presently preferred embodiments of the present invention, not does limitation in any form to the present invention, all at this
Done any modifications, equivalent replacements, and improvements etc., should be included in protection scope of the present invention within the spirit and principle of invention
Within.
Claims (10)
1. preparation method of the one kind containing the benzofuran simultaneously alcohol compound of [2,3-b] pyridine structure, it is characterised in that: including
Following steps,
Step (1) etherification reaction: being raw material together with deposited using guaiacol and the fluoro- 6- picoline of 2- under the conditions of 80~140 DEG C
Sour agent is added in the first solvent, and 3~12h of reaction obtains etherification product, wherein mole of guaiacol and the fluoro- 6- picoline of 2-
Than being 1.0~2.0:1；
Step (2) intramolecular cyclization: under the conditions of 120~140 DEG C, etherification product that step (1) is obtained together with catalyst and
Oxidant is added in the second solvent, reacts 4~12h, obtains the ethers chemical combination containing benzofuran simultaneously [2,3-b] pyridine structure
Object；
Step (3) hydrolysis: under the conditions of 90~110 DEG C, contain benzofuran simultaneously [2,3-b] pyrrole for what step (2) obtained
4~12h is reacted in 1:2.0~5.0 to the ether compound of pyridine structure in molar ratio with 48% hydrobromic acid, obtains containing benzofuran simultaneously
The alcohol compound of [2,3-b] pyridine structure.
2. the preparation side containing the benzofuran simultaneously alcohol compound of [2,3-b] pyridine structure as described in claim 1 a kind of
Method, it is characterised in that: the acid-binding agent in the step (1) is one or more of cesium carbonate, potassium carbonate, sodium carbonate, applies acid
The molar ratio of agent and the fluoro- 6- picoline of 2- is 1.0~2.0:1, and the first solvent is n,N-Dimethylformamide.
3. the preparation side containing the benzofuran simultaneously alcohol compound of [2,3-b] pyridine structure as claimed in claim 2 a kind of
Method, it is characterised in that: the molar ratio of guaiacol and the fluoro- 6- picoline of 2- is 1:1 in the step (1), and reaction temperature is
130 DEG C, reaction time 8h.
4. one kind as described in claims 1 to 3 is any contains the benzofuran simultaneously alcohol compound of [2,3-b] pyridine structure
Preparation method, it is characterised in that: catalyst in the step (2) be palladium acetate, palladium trifluoroacetate, tetrakis triphenylphosphine palladium,
The molar ratio of one or more of tris(dibenzylideneacetone) dipalladium, palladium chloride, catalyst and etherification product be 0.01~
0.2:1.
5. the preparation side containing the benzofuran simultaneously alcohol compound of [2,3-b] pyridine structure as claimed in claim 4 a kind of
Method, it is characterised in that: the oxidant in the step (2) is one or more of silver oxide, copper acetate, silver acetate, oxidation
The molar ratio of agent and etherification product is 1~5:1.
6. the preparation side containing the benzofuran simultaneously alcohol compound of [2,3-b] pyridine structure as claimed in claim 5 a kind of
Method, it is characterised in that: second solvent is one or both of glacial acetic acid, pivalic acid, and the reaction temperature of step (2) is
130 DEG C, reaction time 8h.
7. the preparation side containing the benzofuran simultaneously alcohol compound of [2,3-b] pyridine structure as described in claim 1 a kind of
Method, it is characterised in that: what 48% hydrobromic acid and step (2) obtained in the step (3) contains benzofuran simultaneously [2,3-b] pyridine
The molar ratio of the ether compound of structure is 4.5:1, and reaction temperature is 105 DEG C, reaction time 8h.
8. the preparation side containing the benzofuran simultaneously alcohol compound of [2,3-b] pyridine structure as described in claim 1 a kind of
Method, it is characterised in that: the etherification product that the step (1) obtains is 2- (2- methoxyphenoxy) -6- picoline, the 2-
The extraction process of (2- methoxyphenoxy) -6- picoline are as follows:
Step (1) after the reaction was completed, is toppled in water and is quenched, be extracted with ethyl acetate later, then dry with organic phase anhydrous sodium sulfate
Dry, the rear desolventizing that depressurizes obtains yellow oil, and 2- (2- methoxyphenoxy)-can be obtained with petroleum ether or dehydrated alcohol crystallization
6- picoline.
9. the preparation side containing the benzofuran simultaneously alcohol compound of [2,3-b] pyridine structure as claimed in claim 8 a kind of
Method, it is characterised in that: the ether compound containing benzofuran simultaneously [2,3-b] pyridine structure that the step (2) obtains is 8-
Methoxyl group -2- methyl benzofuran simultaneously [2,3-b] pyridine, the 8- methoxyl group -2- methyl benzofuran simultaneously [2,3-b] pyridine
Extraction process are as follows:
Step (2) after the reaction was completed, is toppled in sodium hydrate aqueous solution, after be extracted with ethyl acetate, then with the anhydrous sulphur of organic phase
Sour sodium is dry, depressurizes desolventizing later and obtains sepia grease, and crossing silicagel column can be obtained 8- methoxyl group -2- methyl benzofuran
And [2,3-b] pyridine crude product.
10. the preparation side containing the benzofuran simultaneously alcohol compound of [2,3-b] pyridine structure as claimed in claim 9 a kind of
Method, it is characterised in that: the reactant extraction process of the step (3) are as follows: after completion of the reaction, be added water quenching reaction, after use second
Acetoacetic ester extraction, then it is dry with organic phase anhydrous sodium sulfate, desolventizing obtains brown solid crude product, and again with toluene ethyl alcohol is tied again
Crystalline substance, it is 2- methyl benzofuran simultaneously [2,3-b] pyridine -8- alcohol that 10 DEG C of suction filtrations, which obtain brown solid,.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110003227A (en) * | 2019-04-26 | 2019-07-12 | 新乡市润宇新材料科技有限公司 | A kind of synthetic method of 2- methyl -8- Methoxvbenzofuran [2,3-b] pyridine |
| CN114736212A (en) * | 2022-04-29 | 2022-07-12 | 临沂大学 | Furo [3,2-b ] indole derivative and synthetic method and application thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103804426A (en) * | 2012-11-09 | 2014-05-21 | 环球展览公司 | Compound, device and concoction relates to iridium complexes with aza-benzo fused ligands |
| CN107805255A (en) * | 2017-09-22 | 2018-03-16 | 中国药科大学 | Furans [3,2 b] pyridine 2 (1H) ketone compounds, preparation method and medical usage |
-
2018
- 2018-08-28 CN CN201810988339.5A patent/CN109096293A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103804426A (en) * | 2012-11-09 | 2014-05-21 | 环球展览公司 | Compound, device and concoction relates to iridium complexes with aza-benzo fused ligands |
| CN107805255A (en) * | 2017-09-22 | 2018-03-16 | 中国药科大学 | Furans [3,2 b] pyridine 2 (1H) ketone compounds, preparation method and medical usage |
Non-Patent Citations (5)
| Title |
|---|
| HIROYUKI KAIDA等: "Construction of Bisbenzofuro[2,3-b:3’,2’-e]pyridines by Palladium-Catalyzed Double Intramolecular Oxidative C-H/C-H Coupling", 《ORGANIC LETTERS》 * |
| HIROYUKI KAIDA等: "Supporting Information forConstruction of Bisbenzofuro[2,3-b:3’,2’-e]pyridines by Palladium-Catalyzed Double Intramolecular Oxidative C-H/C-H Coupling", 《ORGANIC LETTERS》 * |
| YUHEI ITAI等: "Syntheses of Diverse Donor-Substituted Bisbenzofuro[2,3-b:3’,2’-e]pyridines (BBZFPys) via Pd Catalysis, and Their Photophysical Properties", 《THE JOURNAL OF ORGANIC CHEMISTRY》 * |
| 张黯: "《有机化学选论 第2辑 饱和碳原子上的亲核取代反应历程》", 31 October 1987, 高等教育出版社 * |
| 杨丰科等: "《基础有机化学》", 31 August 2001, 化工工业出版社 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110003227A (en) * | 2019-04-26 | 2019-07-12 | 新乡市润宇新材料科技有限公司 | A kind of synthetic method of 2- methyl -8- Methoxvbenzofuran [2,3-b] pyridine |
| CN110003227B (en) * | 2019-04-26 | 2022-03-11 | 新乡市润宇新材料科技有限公司 | Synthetic method of 2-methyl-8-methoxybenzofuran [2,3-b ] pyridine |
| CN114736212A (en) * | 2022-04-29 | 2022-07-12 | 临沂大学 | Furo [3,2-b ] indole derivative and synthetic method and application thereof |
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