Synthesis process of dibenzofuran derivatives

A technology of dibenzofuran and derivatives, which is applied in the fields of drug synthesis and material chemistry, can solve problems such as harsh reaction conditions, and achieve the effect of easy reaction and good universality of reaction

Inactive Publication Date: 2018-08-31
CHANGZHOU UNIV
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

At present, there is harsh reaction condition in the method reported in the literature, need to use defectives such as expensive silver reagent, palladium or rhod

Method used

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  • Synthesis process of dibenzofuran derivatives
  • Synthesis process of dibenzofuran derivatives

Examples

Experimental program
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Example Embodiment

[0015] (1). Preparation of cyclic diaryliodonium salt 1:

[0016] Under an ice bath, slowly add mCPBA (1.73g, 7.5mmol) to the mixed solution of 2-iodobiaryl (5.0mmol) and DCM (20mL), stir at room temperature for 40 minutes, and slowly add TfOH (1.32mL, 15.0 mmol). Stir at room temperature for 2 hours, then remove the DCM by evaporation in vacuo. Ether (15 mL) was added to the solid residue, stirred for 20 minutes, filtered, washed with ether (about 5 mL) three times and dried in vacuo to obtain cyclic diaryliodonium trifluoromethanesulfonate.

[0017]

Example Embodiment

[0018] Example 1

[0019] Dibenzoiodine pentacyclic trifluoromethanesulfonate (1.0mmol), 1,10-phenanthroline (0.1mmol), cuprous iodide (5mmol%), K 2 CO 3 (0.2mmol) and 2mL of water were added to a 15mL pressure-resistant tube, stirred at 100°C, reacted for 24 hours, petroleum ether was recrystallized to obtain a yield of 2a of 96%. 1 H NMR(400MHz, CDCl 3 ) 1 H NMR(400MHz, CDCl 3 )δ7.98(d,J=7.7Hz,2H), 7.60(d,J=8.2Hz,2H), 7.48(t,J=7.6Hz,2H), 7.37(t,J=7.5Hz,2H) .

Example Embodiment

[0020] Example 2

[0021] Combine 3-methyl-dibenzoiodine pentacyclic trifluoromethanesulfonate (1.0mmol), 1,10-phenanthroline (0.1mmol), cuprous iodide (5mmol%), K 2 CO 3 (0.2 mmol) and 2 mL of water were added to a 15 mL pressure-resistant tube, stirred at 100° C., reacted for 24 hours, and petroleum ether was recrystallized to obtain a yield of 94% of 2b. 1 H NMR(400MHz, CDCl 3 )δ7.95–7.91(m,1H), 7.84(d,J=7.9Hz,1H), 7.57(d,J=8.2Hz,1H), 7.47–7.38(m,2H),7.34(td,J =7.5,0.8Hz,1H),7.19(d,J=7.8Hz,1H),2.55(s,3H).

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Abstract

The invention relates to a synthesis process of dibenzofuran derivatives, and relates to the fields of natural products with biological activity, medicaments and material chemistry. The used raw material is a cyclic diphenyliodonium trifluoromethanesulfonate derivative, a reaction is carried out in a water phase at 100 DEG C under the catalysis of a 1,10-phenanthroline ligand and cuprous iodide, and a series of dibenzofuran derivatives are obtained. With the adoption of the method provided by the invention, the dibenzofuran derivatives can be obtained by carrying out the reaction at the temperature of 100 DEG C for 24 hours, and the yield is 60-96%. In the reaction, water is taken as a reagent as well as a solvent for participating in the reaction, and the simple, convenient, green, economic, and novel method is provided for synthesizing the derivatives.

Description

technical field [0001] The invention relates to a synthesis process for preparing dibenzofuran derivatives, belonging to the technical fields of medicine synthesis and material chemistry. Background technique [0002] Dibenzofuran skeletons are widely used in medicinal chemistry and material science due to their weak biochemical stress response, excellent heat resistance and photoelectric properties. Biologically active furobufen, DB03682, and photoelectric materials used in phosphorescent organic light-emitting devices (PHOLED) and other functional compounds all contain dibenzofuran units. At present, there is harsh reaction condition in the method reported in the literature, need to use defectives such as expensive silver reagent, palladium or rhodium catalyst in the preparation process, so the synthetic method of simple efficient, green dibenzofuran derivative still has important development. significance. [0003] We use cyclic diphenyliodonium trifluoromethanesulfonat...

Claims

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Application Information

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IPC IPC(8): C07D307/91
CPCC07D307/91
Inventor 李剑柏淑华刘莉
Owner CHANGZHOU UNIV
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