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Synthesis method of boron-nitrogen benzanthracene fused-ring compound

A synthesis method, the technology of benzanthracene, applied in the field of organic synthesis, can solve the problems of poor selectivity, achieve the effects of less environmental pollution, strong reaction specificity, and avoid the use of sensitive reagents

Inactive Publication Date: 2019-05-21
JIUJIANG UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The method of the present invention is different from the synthesis strategy of many boron nitrogen compounds, that is, the boron nitrogen aromatic ring is used as the basic skeleton to derivatize it, which avoids the problem of poor selectivity of the direct boronation reaction, and at the same time avoids the use of sensitive reagents. A kind of synthesis method of borazine-benzanthracene condensed ring compound with wide application of raw materials, simple reaction, strong reaction specificity and high yield

Method used

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  • Synthesis method of boron-nitrogen benzanthracene fused-ring compound
  • Synthesis method of boron-nitrogen benzanthracene fused-ring compound
  • Synthesis method of boron-nitrogen benzanthracene fused-ring compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Synthesis of compound 1: take a 50mL dry Schlenk bottle, vacuumize and change the argon for 3 times, under the protection of argon, add monobromoborazanthracene (230mg, 0.5mmol), B2Pin2 (150mg, 0.75mmol), Pd( dppf)Cl2 (6mg, 2mol%), Na2CO3 (80mg, 0.75mmol), and introduce anhydrous and oxygen-free solvent tetrahydrofuran (5mL). Under the protection of argon, react at 60°C for about 16h. After the reaction is completed, after the temperature of the system drops to room temperature, extract with dichloromethane (4*10mL) and water (50mL), combine the organic phases, dry them with anhydrous sodium sulfate, and reduce pressure The solvent was removed and separated by column chromatography (developing solvent: n-hexane:dichloromethane=5:1) to obtain 170 mg of a yellow-green solid with a yield of 67%.

[0021] The nuclear magnetic analysis data of this compound are as follows:

[0022] 1H NMR (400MHz, CDCl3): δ9.18 (1H, s, NH), 8.89 (1H, s), 7.94 (1H, dd, J1 = 4Hz, J2 = 8Hz), 7...

Embodiment 2

[0025] Synthesis of compound 2: Take a 50mL dry Schlenk bottle, vacuumize and change argon three times, under the protection of argon, add monobromoborazanthracene (230mg, 0.5mmol), diphenylamine (102mg, 0.6mmol), alkene Propylpalladium chloride dimer (2mg, 1mol%), JohnPhos ligand ((3mg, 2mol%), NaOt-Bu (67mg, 0.7mmol), import anhydrous oxygen-free solvent toluene (4mL). Argon protection At 80°C for about 16 hours, the reaction was completed. After the temperature of the system dropped to room temperature, the solid insolubles were removed by filtration, washed with dichloromethane, and the solvent was removed under reduced pressure. 5:1), 227 mg of yellow solid was obtained, and the yield was 83%.

[0026] The nuclear magnetic analysis data of this compound are as follows:

[0027] 1 H NMR (400MHz, CDCl 3 ):δ8.81(1H,s,NH),8.18(1H,s),7.99(1H,s),7.69(1H,d,J=8Hz),7.50-7.58(2H,m),7.11-7.30 (21H,m),7.02-7.08(2H,m). 11 B NMR (128MHz, CDCl 3 ): δ31.36. 13 C NMR (101MHz, CDCl ...

Embodiment 3

[0030] Synthesis of compound 3: take a 50mL dry Schlenk bottle, vacuumize and change argon three times, under the protection of argon, add dibromoborazanthracene (270mg, 0.5mmol), diphenylamine (204mg, 1.2mmol), diphenylamine (204mg, 1.2mmol), ene Propylpalladium chloride dimer (4mg, 2mol%), JohnPhos ligand (6mg, 4mol%), NaOt-Bu (134mg, 1.4mmol) were introduced into anhydrous and oxygen-free solvent toluene (10mL). Under the protection of argon, react at 80°C for about 16h. After the reaction is completed, when the temperature of the system drops to room temperature, remove the solid insoluble matter by filtration, wash with dichloromethane, remove the solvent under reduced pressure, and separate by column chromatography (developing agent: n-hexane: two Chloromethane=5:1), to obtain 261 mg of yellow-green solid, yield 73%.

[0031] The nuclear magnetic analysis data of this compound are as follows:

[0032] 1 H NMR (400MHz, CDCl 3 ):δ8.79(1H,s,NH),8.16(1H,d,J=4Hz),7.79(1H,s),...

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Abstract

Provided is a synthesis method of a boron-nitrogen benzanthracene fused-ring compound. The synthesis method of the boron-nitrogen benzanthracene fused-ring compound comprises the step of adopting boron-nitrogen benzanthracene halide, a coupling precursor, a catalyst, a ligand and the like as raw materials for a reaction at the temperature of 60-140 DEG C for 3-24 hours under the protection of nitrogen to obtain the boron-nitrogen benzanthracene fused-ring compound. The boron-nitrogen benzanthracene halide is a boron-nitrogen benzanthracene monobromo (chloro)-substituted or dibromo (chloro)-substituted derivative; the coupling precursor is selected from diphenylamine and derivatives thereof, pyrene boric acid and derivatives thereof and the like. The catalyst is selected from palladium acetate, ditriphenylphosphine palladium dichloride and the like. The ligand is selected from triphenyl phosphine, tricyclohexyl phosphine and the like. According to the method, a boron-nitrogen aromatic ring is used as a basic framework for derivatization, so that the problem of poor selectivity of a direct boronization reaction is avoided, and meanwhile, the use of a sensitive reagent is avoided. Theprovided synthesis method of the boron-nitrogen benzanthracene fused-ring compound is wide in application range of raw materials, simple in reaction, high in reaction specificity and yield and smallin environmental pollution, and the variety of boron-nitrogen compounds is enriched.

Description

technical field [0001] The invention relates to a synthesis method of a group of borazine-benzanthracene condensed ring compounds, and specifically belongs to the technical field of organic synthesis. Background technique [0002] The development of synthetic methods is an important part of the research on borazine chemistry, and it is also one of the challenges in the research of borazine chemistry. At present, the synthesis methods of borazine heterocyclic compounds are still limited. Except for the more commonly used electrophilic substitution reactions, although new synthetic routes have been continuously proposed, their applicability is relatively narrow, and they are only for a specific structure type. The boron nitrogen compound is effective, and has the disadvantages of harsh reaction conditions, unstable raw materials, difficult precursor synthesis, complex reaction process, cumbersome post-treatment, poor substrate compatibility, and difficult product functionaliza...

Claims

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Application Information

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IPC IPC(8): C07F5/02C07F5/04C07F7/08
Inventor 黄华南周影
Owner JIUJIANG UNIVERSITY
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