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Method for electrochemical synthesis of carbazole compound

A technology for carbazoles and compounds, which is applied in the field of electrochemical synthesis of carbazoles, can solve problems such as unreported, and achieve the effects of simple and easy operation, easy handling and mild reaction conditions

Active Publication Date: 2020-06-16
QILU UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, the electrochemical synthesis of carbazole compounds has not been reported.

Method used

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  • Method for electrochemical synthesis of carbazole compound
  • Method for electrochemical synthesis of carbazole compound
  • Method for electrochemical synthesis of carbazole compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059]

[0060] In a 10mL three-necked flask, add 2-benzenesulfonylaminobiphenyl (0.2mmol), tetrabutylammonium hexafluorophosphate (0.4mmol), tetrabutylammonium iodide (0.02mmol), trifluoroethanol (5ml), Dichloromethane (5ml). The carbon rod was used as the anode, and the platinum sheet was used as the cathode. Under the conditions of room temperature and nitrogen atmosphere, the electrolytic reaction was performed with a constant current of 1.7mA for 12 hours. After the reaction was completed, the solvent was removed with a rotary evaporator, and the residue was purified by flash silica gel column chromatography (ethyl acetate:petroleum ether=1:50) to obtain a white solid product with a yield of 90%;

[0061] 1 H NMR (400MHz, CDCl 3 )δ8.25(d, J=8.4Hz, 2H), 7.79(d, J=7.7Hz, 2H), 7.72(m, 2H), 7.39(t, J=7.6Hz, 2H), 7.32(t, J=7.2Hz, 1H), 7.26(t, J=7.5Hz, 2H), 7.19(t, J=7.7Hz, 2H).

[0062] 13 C NMR (101MHz, CDCl 3 )δ138.39, 137.94, 133.77, 129.02, 127.44, 126.45, 126.43,...

Embodiment 2

[0064]

[0065] In a 10mL three-necked flask, add N-(4'-methoxy-[1,1'-biphenyl]-2-yl)benzenesulfonamide (0.2mmol), tetrabutylammonium hexafluorophosphate (0.4mmol) , tetrabutylammonium iodide (0.02mmol), trifluoroethanol (5ml), dichloromethane (5ml). The carbon rod was used as the anode, and the platinum sheet was used as the cathode. Under the conditions of room temperature and nitrogen atmosphere, the electrolytic reaction was performed with a constant current of 1.7mA for 12 hours. After the reaction was completed, the solvent was removed with a rotary evaporator, and the residue was purified by flash silica gel column chromatography (ethyl acetate:petroleum ether=1:50) to obtain a white solid product with a yield of 95%;

[0066] 1 H NMR (400MHz, CDCl 3 )δ8.18(d,J=8.3Hz,1H),7.80(s,1H),7.72-7.63(m,4H),7.34-7.28(m,2H),7.23-7.18(m,3H),6.85 (d,J=8.5Hz,1H),3.84(s,3H).

[0067] 13 C NMR (101MHz, CDCl 3 )δ159.84, 139.71, 138.32, 137.87, 133.82, 129.06, 126.54, 126.44, 12...

Embodiment 3

[0069]

[0070] Add N-(2-(benzo[d][1,3]dioxa-5 base)phenyl)benzenesulfonamide (0.2mmol), tetrabutylammonium hexafluorophosphate (0.4 mmol), tetrabutylammonium iodide (0.02mmol), trifluoroethanol (5ml), dichloromethane (5ml). The carbon rod was used as the anode, and the platinum sheet was used as the cathode. Under the conditions of room temperature and nitrogen atmosphere, the electrolytic reaction was performed with a constant current of 1.7mA for 12 hours. After the reaction was completed, the solvent was removed by a rotary evaporator, and the residue was purified by flash silica gel column chromatography (ethyl acetate:petroleum ether=1:50) to obtain a white solid product with a yield of 93%;

[0071] 1 H NMR (400MHz, CDCl 3 )δ8.16(d, J=8.3Hz, 1H), 7.75(s, 1H), 7.65(d, J=8.7Hz, 2H), 7.59(d, J=6.9Hz, 1H), 7.34-7.26( m,2H),7.24-7.16(m,3H),7.10(s,1H),5.94(s,2H).

[0072] 13 C NMR (101MHz, CDCl 3 )δ 148.19, 145.45, 138.37, 137.67, 133.78, 133.31, 129.03, 126.76, 126....

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Abstract

The invention relates to a method for electrochemical synthesis of a carbazole compound. The method comprises the following steps: taking an N-substituted acylamino biphenyl derivative as a substrate,adding the substrate and an electrolyte into an organic solvent, inserting an electrode, stirring, carrying out electrolytic reaction, stirring in nitrogen at room temperature by taking a carbon rodas an anode and a platinum sheet electrode as a cathode, carrying out constant-current reaction, removing the solvent by using a rotary evaporator after the reaction is finished, and carrying out rapid silica gel column chromatography purification on residues to obtain a product. According to the method, the reaction is electrically promoted, expensive metal catalysts and other oxidizing agents are not needed, the reaction can be carried out mildly at the room temperature, the selectivity is good, the yield is high, the whole process is simple and easy to implement, and the concept of green chemistry is met. According to the method, no extra oxidant is needed, the method is simple and efficient, the substrate is wide in applicability, and the yield of compounds with different substituent effect groups can be very high. The preparation method is simple, economical and environment-friendly, and has a certain industrial prospect.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a method for electrochemically synthesizing carbazole compounds. Background technique [0002] Carbazole exists naturally in high temperature tar fractions. Carbazole is a class of electron-rich nitrogen-containing heterocyclic compounds with a large π-conjugated rigid structure. This unique structure makes it and its derivatives exhibit many excellent photoelectric properties and biological activities. As important intermediates of fine chemicals, carbazole compounds are widely used in many fields. Natural carbazole alkaloid itself has antigenicity to microorganisms, and people modify its structure on the basis of it to obtain compounds with better biological activity. Carbazole and its derivatives are widely used in the field of medicine. With the development of science and technology, the application of carbazole and its derivatives in other fields is also favored ...

Claims

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Application Information

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IPC IPC(8): C25B3/02C25B3/23
CPCC25B3/23
Inventor 陈建宾张攀
Owner QILU UNIV OF TECH
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