CN114456033B - Preparation method of fluoranthene derivative - Google Patents

Preparation method of fluoranthene derivative Download PDF

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CN114456033B
CN114456033B CN202210140470.2A CN202210140470A CN114456033B CN 114456033 B CN114456033 B CN 114456033B CN 202210140470 A CN202210140470 A CN 202210140470A CN 114456033 B CN114456033 B CN 114456033B
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fluoranthene derivative
fluoranthene
organic solvent
reaction
thiophene
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CN114456033A (en
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周刚
谢寿东
苏仰哲
郭泽颖
宗浩
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Fudan University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
    • C07C1/32—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen
    • C07C1/321—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen the hetero-atom being a non-metal atom
    • C07C1/322—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen the hetero-atom being a non-metal atom the hetero-atom being a sulfur atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction
    • C07C17/358—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction by isomerisation
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
    • C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/08—Hydrogen atoms or radicals containing only hydrogen and carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/78—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/52—Ortho- or ortho- and peri-condensed systems containing five condensed rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/54—Ortho- or ortho- and peri-condensed systems containing more than five condensed rings

Abstract

The invention relates to a preparation method of fluoranthene derivatives, which comprises the following steps: 1-thiophene-8-alkynyl naphthalene compound is used as a raw material, and cyclization reaction is carried out in an organic solvent, so that the fluoranthene derivative is obtained. Compared with the prior art, the invention provides a simple method for synthesizing the fluoranthene derivative by intramolecular [4+2] cyclization between thiophene and alkyne under the condition of no catalysis, and various functional groups can be accurately introduced into different positions of a fluoranthene skeleton by simply adjusting substituents on the thiophene and the alkyne, and conjugation of the fluoranthene can be extended in different directions. The preparation method can be used for synthesizing fluoranthene derivatives with functional substituents at different positions, and has the advantages of few steps, high yield, low cost, easy separation and the like.

Description

Preparation method of fluoranthene derivative
Technical Field
The invention belongs to the technical field of fluoranthene derivatives, and relates to a preparation method of a fluoranthene derivative.
Background
Fluoranthene is one of the smallest non-alternating hydrocarbon units that are formed by joining benzene and naphthalene with a five-membered ring. The fluoranthene derivative has unique photoelectric characteristics, has been widely applied at present, and has excellent application value in the fields of organic light emitting diodes, organic field effect transistors and fluorescence sensors.
However, although several synthetic methods have been developed by researchers to prepare fluoranthene derivatives, these methods generally suffer from relatively low selectivity and reactivity, and it is difficult to functionally modify the fluoranthene backbone at different sites.
Disclosure of Invention
The invention aims to provide a preparation method of fluoranthene derivatives, which does not need to use a catalyst and has the advantages of high yield, low cost, simple synthesis process and the like.
The aim of the invention can be achieved by the following technical scheme:
a method for preparing a fluoranthene derivative, comprising the steps of: and (3) taking the 1-thiophene-8-alkynyl naphthalene compound as a raw material, and performing cyclization reaction in an organic solvent to obtain the fluoranthene derivative.
Further, the method specifically comprises the following steps: dissolving 1-thiophene-8-alkynyl naphthalene compounds in an organic solvent, then carrying out cyclization reaction, and separating and purifying to obtain the fluoranthene derivative.
Further, the structural formula of the 1-thiophene-8-alkynyl naphthalene compound is as follows:
wherein R is 1 To R 10 Is a substituent, for example, hydrogen, aliphatic hydrocarbon group, aromatic hydrocarbon group, heterocyclic aryl group, condensed ring aryl group, and the like.
The synthetic route is as follows:
preferably, R 1 To R 10 Each independently selected from the following groups: hydrogen, -C n H 2n+1 、-C n H 2n OH、 -C n H n OC m H 2m+1 、-F、-Cl、-Br、-I、-NH 2 、-NHC n H 2n+1 、-N(C n H 2n+1 ) 2 、-N + (C n H 2n+1 ) 3 、 -NHCOC n H 2n+1 、-OH、-OC n H 2n+1 、-OCOC n H 2n+1 、-OC n H n OC m H 2m+1 、-COOH、 -COOC m H 2m+1 、-C n H 2n COOH、-C n H 2n COOC m H 2m+1 、-NO 2 、-CF 3 、-CCl 3 、-CN、-CHO、 -SO 3 H、
Wherein n=1-10 and m=1-10.
Preferably, R 11 To R 19 Each independently selected from the following groups: hydrogen, -C n H 2n+1 、-C n H 2n OH、 -C n H n OC m H 2m+1 、-F、-Cl、-Br、-I、-NH 2 、-NHC n H 2n+1 、-N(C n H 2n+1 ) 2 、-N + (C n H 2n+1 ) 3 、 -NHCOC n H 2n+1 、-OH、-OC n H 2n+1 、-OCOC n H 2n+1 、-OC n H n OC m H 2m+1 、-COOH、 -COOC m H 2m+1 、-C n H 2n COOH、-C n H 2n COOC m H 2m+1 、-NO 2 、-CF 3 、-CCl 3 、-CN、-CHO、 -SO 3 H。
Further, the boiling point of the organic solvent is higher than 100 ℃.
Preferably, the organic solvent comprises one or more of o-xylene, N-methylpyrrolidone, N-dimethylformamide, mesitylene, ethylene glycol, cyclohexanone, o-dichlorobenzene, diphenyl ether, nitrobenzene, sulfolane, diethylene glycol dimethyl ether, pyridine, m-xylene, cyclohexanol, o-cresol, formamide, quinoline, N-methylformamide.
Further, in the cyclization reaction process, the reaction temperature is higher than 100 ℃ and the reaction time is longer than 1 hour.
Preferably, the reaction temperature is 120-285 ℃ and the reaction time is 1.5-10 hours during the cyclization reaction.
Further, the separation and purification process comprises the following steps: the organic solvent is removed to obtain a crude product, which is then subjected to column chromatography.
Compared with the prior art, the invention has the following characteristics:
1) The invention provides a simple method for synthesizing fluoranthene derivatives by intramolecular [4+2] cyclization between thiophene and alkyne under the condition of no catalysis. By simply adjusting the substituents on thiophene and alkyne, not only can various functional groups be accurately introduced into different positions of the fluoranthene skeleton, but also the conjugation of fluoranthene can be extended in different directions. The preparation method has simple synthesis process, can be used for synthesizing fluoranthene derivatives with functional substituents at different positions, and also provides an effective way for constructing large polycyclic aromatic hydrocarbon containing fluoranthene parts.
2) The preparation method of the fluoranthene derivative does not need to add any catalyst, has the advantages of few steps, high yield, low cost, easy separation and the like, and the prepared fluoranthene derivative has wide application prospect in organic light-emitting devices.
Detailed Description
The present invention will be described in detail with reference to specific examples. The present embodiment is implemented on the premise of the technical scheme of the present invention, and a detailed implementation manner and a specific operation process are given, but the protection scope of the present invention is not limited to the following examples.
The invention provides a preparation method of fluoranthene derivatives, which comprises the following steps: 1-thiophene-8-alkynyl naphthalene compound is used as a raw material, and cyclization reaction is carried out in an organic solvent, so that the fluoranthene derivative is obtained. The method specifically comprises the following steps: dissolving 1-thiophene-8-alkynyl naphthalene compound in an organic solvent, then carrying out cyclization reaction, and separating and purifying to obtain the fluoranthene derivative.
Wherein, the structural formula of the 1-thiophene-8-alkynyl naphthalene compound is as follows:
R 1 to R 10 Is a substituent.
Preferably, R 1 To R 10 Each independently selected from the following groups: hydrogen, -C n H 2n+1 、-C n H 2n OH、 -C n H n OC m H 2m+1 、-F、-Cl、-Br、-I、-NH 2 、-NHC n H 2n+1 、-N(C n H 2n+1 ) 2 、-N + (C n H 2n+1 ) 3 、 -NHCOC n H 2n+1 、-OH、-OC n H 2n+1 、-OCOC n H 2n+1 、-OC n H n OC m H 2m+1 、-COOH、 -COOC m H 2m+1 、-C n H 2n COOH、-C n H 2n COOC m H 2m+1 、-NO 2 、-CF 3 、-CCl 3 、-CN、-CHO、 -SO 3 H、
Wherein n=1-10 and m=1-10.
Preferably, R 11 To R 19 Each independently selected from the following groups: hydrogen, -C n H 2n+1 、-C n H 2n OH、 -C n H n OC m H 2m+1 、-F、-Cl、-Br、-I、-NH 2 、-NHC n H 2n+1 、-N(C n H 2n+1 ) 2 、-N + (C n H 2n+1 ) 3 、 -NHCOC n H 2n+1 、-OH、-OC n H 2n+1 、-OCOC n H 2n+1 、-OC n H n OC m H 2m+1 、-COOH、 -COOC m H 2m+1 、-C n H 2n COOH、-C n H 2n COOC m H 2m+1 、-NO 2 、-CF 3 、-CCl 3 、-CN、-CHO、 -SO 3 H。
The boiling point of the organic solvent is higher than 100 ℃, preferably comprising one or more of o-xylene, N-methylpyrrolidone, N-dimethylformamide, mesitylene, ethylene glycol, cyclohexanone, o-dichlorobenzene, diphenyl ether, nitrobenzene, sulfolane, diethylene glycol dimethyl ether, pyridine, m-xylene, cyclohexanol, o-cresol, formamide, quinoline, N-methylformamide.
In the cyclization reaction process, the reaction temperature is higher than 100 ℃ and the reaction time is longer than 1 hour. Preferably, the reaction temperature is 120-285 ℃ and the reaction time is 1.5-10 hours during the cyclization reaction.
The separation and purification process comprises the following steps: the organic solvent is removed to obtain a crude product, which is then subjected to column chromatography.
Example 1:
preparation of fluoranthene derivative 1:
602 mg of 1a were dissolved in 25mL of o-xylene and stirred at 140℃for 8 hours. After the reaction is finished, removing the organic solvent in the reaction system, and separating and purifying the crude product by column chromatography to obtain 540mg of fluoranthene derivative 1 with 89% yield.
Example 2:
preparation of fluoranthene derivative 2:
49mg of 2a was dissolved in 6 mLN-methylpyrrolidone and stirred at 180℃for 4 hours. After the reaction is finished, removing the organic solvent in the reaction system, and separating and purifying the crude product by column chromatography to obtain 42mg of fluoranthene derivative 2 with the yield of 85%.
Example 3:
preparation of fluoranthene derivative 3:
72mg 3a were dissolved in 7mLN, N-dimethylformamide and stirred at 160℃for 7 hours. After the reaction is finished, removing the organic solvent in the reaction system, and separating and purifying the crude product by column chromatography to obtain 60mg of fluoranthene derivative 3 with the yield of 83%.
Example 4:
preparation of fluoranthene derivative 4:
148mg of 4a were dissolved in mesitylene and stirred for 6 hours at 165 ℃. After the reaction is finished, removing the organic solvent in the reaction system, and separating and purifying the crude product by column chromatography to obtain 120mg of fluoranthene derivative 4 with the yield of 81%.
Example 5:
preparation of fluoranthene derivative 5:
51mg of 5a was dissolved in 6mL of ethylene glycol and stirred at 200℃for 3 hours. After the reaction is finished, removing the organic solvent in the reaction system, and separating and purifying the crude product by column chromatography to obtain 40mg of fluoranthene derivative 5 with the yield of 78%.
Example 6:
preparation of fluoranthene derivative 6:
270mg of 6a were dissolved in 18mL of cyclohexanone and stirred at 155℃for 8 hours. After the reaction is finished, removing the organic solvent in the reaction system, and separating and purifying the crude product by column chromatography to obtain 130mg of fluoranthene derivative 6 with the yield of 48%.
Example 7:
preparation of fluoranthene derivative 7:
303mg of 7a was dissolved in 20mL of o-dichlorobenzene and stirred at 175℃for 4 hours. After the reaction is finished, removing the organic solvent in the reaction system, and separating and purifying the crude product by column chromatography to obtain 200mg of fluoranthene derivative 7 with the yield of 66%.
Example 8:
preparation of fluoranthene derivative 8:
56mg 8a was dissolved in 6mL of diphenyl ether and stirred at 240℃for 2 hours. After the reaction is finished, removing the organic solvent in the reaction system, and separating and purifying the crude product by column chromatography to obtain 39mg of fluoranthene derivative 8 with the yield of 69%.
Example 9:
preparation of fluoranthene derivative 9:
105mg of 9a are dissolved in 10mL of nitrobenzene and stirred at 200℃for 3 hours. After the reaction is finished, removing the organic solvent in the reaction system, and separating and purifying the crude product by column chromatography to obtain 80mg of fluoranthene derivative 9 with 76% yield.
Example 10:
preparation of fluoranthene derivative 10:
80mg 10a was dissolved in 8mL sulfolane and stirred at 285℃for 1.5 hours. After the reaction is finished, removing the organic solvent in the reaction system, and separating and purifying the crude product by column chromatography to obtain 48mg of fluoranthene derivative 10 with the yield of 60%.
Example 11:
preparation of fluoranthene derivative 11:
60mg of 11a was dissolved in 7mL of diethylene glycol dimethyl ether and stirred at 180℃for 5 hours. After the reaction is finished, removing the organic solvent in the reaction system, and separating and purifying the crude product by column chromatography to obtain 33mg of fluoranthene derivative 11 with the yield of 55%.
Example 12:
preparation of fluoranthene derivative 12:
61mg 12a was dissolved in 7mL of pyridine and stirred at 120℃for 10 hours. After the reaction, removing the organic solvent in the reaction system, and separating and purifying the crude product by column chromatography to obtain 43mg of fluoranthene derivative 12 with 71% yield.
Example 13:
preparation of fluoranthene derivative 13:
43mg 13a are dissolved in 6mL of meta-xylene and stirred at 140℃for 7 hours. After the reaction is finished, removing the organic solvent in the reaction system, and separating and purifying the crude product by column chromatography to obtain 20mg of fluoranthene derivative 13 with the yield of 47%.
Example 14:
preparation of fluoranthene derivative 14:
61mg of 14a were dissolved in 7mL of cyclohexanol and stirred at 165℃for 5.5 hours. After the reaction is finished, removing the organic solvent in the reaction system, and separating and purifying the crude product by column chromatography to obtain 41mg of fluoranthene derivative 14 with 67% yield.
Example 15:
preparation of fluoranthene derivative 15:
69mg of 15a were dissolved in 7mL of o-cresol and stirred for 3 hours at 195 ℃. After the reaction is finished, removing the organic solvent in the reaction system, and separating and purifying the crude product by column chromatography to obtain 49mg of fluoranthene derivative 15 with the yield of 71%.
Example 16:
preparation of fluoranthene derivative 16:
124mg 16a was dissolved in 12mL formamide and stirred at 220℃for 2 hours. After the reaction is finished, removing the organic solvent in the reaction system, and separating and purifying the crude product by column chromatography to obtain 82mg of fluoranthene derivative 16 with the yield of 66%.
Example 17:
preparation of fluoranthene derivative 17:
573mg of 17a was dissolved in 23mL of quinoline and stirred at 240℃for 1 hour. After the reaction is finished, removing the organic solvent in the reaction system, and separating and purifying the crude product by column chromatography to obtain 430mg of fluoranthene derivative 17 with 75% yield.
Example 18:
preparation of fluoranthene derivative 18:
50mg of 18a was dissolved in 7mL of N-methylformamide and stirred at 185℃for 4 hours. After the reaction is finished, removing the organic solvent in the reaction system, and separating and purifying the crude product by column chromatography to obtain 30mg of fluoranthene derivative 18 with 61% yield.
The previous description of the embodiments is provided to facilitate a person of ordinary skill in the art in order to make and use the present invention. It will be apparent to those skilled in the art that various modifications can be readily made to these embodiments and the generic principles described herein may be applied to other embodiments without the use of the inventive faculty. Therefore, the present invention is not limited to the above-described embodiments, and those skilled in the art, based on the present disclosure, should make improvements and modifications without departing from the scope of the present invention.

Claims (3)

1. A method for preparing a fluoranthene derivative, which is characterized by comprising the following steps: taking 1-thiophene-8-alkynyl naphthalene compounds as raw materials, and performing cyclization reaction in an organic solvent to obtain the fluoranthene derivative;
wherein the structural formula of the 1-thiophene-8-alkynyl naphthalene compound is as follows:
，
the structural formula of the fluoranthene derivative is as follows:
，
wherein R is 1 To R 10 Is a substituent;
R 1 to R 10 Each independently selected from the following groups: hydrogen, -C n H 2n+1 、-C n H 2n OH、-F、-Cl、-Br、-I、-NH 2 、-NHC n H 2n+1 、-N(C n H 2n+1 ) 2 、-NHCOC n H 2n+1 、-OH、-OC n H 2n+1 、-OCOC n H 2n+1 、-COOH、-COOC m H 2m+1 、-C n H 2n COOH、-C n H 2n COOC m H 2m+1 、-NO 2 、-CF 3 、-CCl 3 、-CN、-CHO、-SO 3 H、
Wherein n=1-10, m=1-10;
the organic solvent is one of o-xylene, N-methylpyrrolidone, N-dimethylformamide, mesitylene, ethylene glycol, cyclohexanone, o-dichlorobenzene, diphenyl ether, nitrobenzene, sulfolane, diethylene glycol dimethyl ether, pyridine, m-xylene, cyclohexanol, o-cresol, formamide, quinoline or N-methylformamide;
R 11 to R 19 Each independently selected from the following groups: hydrogen, -C n H 2n+1 、-C n H 2n OH、-C n H n OC m H 2m+1 、-F、-Cl、-Br、-I、-NH 2 、-NHC n H 2n+1 、-N(C n H 2n+1 ) 2 、-N + (C n H 2n+1 ) 3 、-NHCOC n H 2n+1 、-OH、-OC n H 2n+1 、-OCOC n H 2n+1 、-OC n H n OC m H 2m+1 、-COOH、-COOC m H 2m+1 、-C n H 2n COOH、-C n H 2n COOC m H 2m+1 、-NO 2 、-CF 3 、-CCl 3 、-CN、-CHO、-SO 3 H；
In the cyclization reaction process, the reaction temperature is 120-285 ℃, and the reaction time is 1.5-10 hours.
2. The method for preparing a fluoranthene derivative according to claim 1, which is characterized in that the method specifically comprises: dissolving 1-thiophene-8-alkynyl naphthalene compounds in an organic solvent, then carrying out cyclization reaction, and separating and purifying to obtain the fluoranthene derivative.
3. The method for preparing a fluoranthene derivative according to claim 2, wherein the separation and purification process comprises: the organic solvent is removed to obtain a crude product, which is then subjected to column chromatography.
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