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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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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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 rhodium catalyst in the preparation process, so the synthetic method of simple efficient, green dibenzofuran derivative still has important development. significance

Method used

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

Examples

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preparation example Construction

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

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

[0017]

Embodiment 1

[0019] Dibenzoiodopentacyclic trifluoromethanesulfonate (1.0mmol), 1,10-phenanthroline (0.1mmol), cuprous iodide (5mmol%), K 2 CO 3 (0.2mmol) and 2mL of water were added into a 15mL pressure-resistant tube, stirred at 100°C, and reacted for 24 hours. The yield of 2a obtained by petroleum ether recrystallization was 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) .

Embodiment 2

[0021] 3-Methyl-dibenzoiodopentacyclic 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, and reacted for 24 hours. The yield of 2b obtained by petroleum ether recrystallization was 94%. 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