Preparation method of polysubstituted benzofuran derivative

A technology for benzofuran and derivatives, which is applied in the field of preparation of multi-substituted benzofuran derivatives, can solve problems such as pollution and complicated preparation methods, and achieve the effect of strong operability and simple process

Active Publication Date: 2016-06-15
北京普诺旺康医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Aiming at the above-mentioned technical problems in the prior art, the present invention provides a method for preparing multi-subst

Method used

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  • Preparation method of polysubstituted benzofuran derivative
  • Preparation method of polysubstituted benzofuran derivative
  • Preparation method of polysubstituted benzofuran derivative

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0018] Example 12-Phenyl-3-(thiophenyl)benzofuran

[0019]

[0020] In a 25mL three-necked flask, add D-1 (220mg, 1mmol), then add Cs 2 CO 3 (652mg, 2mmol), diphenyl disulfide (109mg, 0.5mmol), L-proline (34.5mg, 0.3mmol), cuprous iodide (19mg, 0.1mmol), phenylacetylene (102mg, 1mmol) , 5mL DMSO, under the protection of nitrogen, react in an oil bath at 90°C for 20 hours. After cooling, add 5 mL of water and extract with 5 mL of ethyl acetate each time. After repeating four times, the extract is washed with saturated brine and anhydrous sulfuric acid The sodium was dried, filtered, and the liquid was distilled under reduced pressure. The distillate was separated by a silica gel column (the eluent was petroleum ether) to obtain 248.4 mg of a yellow viscous liquid with a yield of 82%.

[0021] 1 HNMR(500MHz, CDCl 3 )δ7.67–7.58(m,2H), 7.58–7.49(m,2H), 7.38(t,J=7.4Hz,2H), 7.35–7.27(m,5H), 7.21(dd,J=12.4, 4.6Hz, 2H), 7.11 (t, J = 7.3Hz, 1H).

Example Embodiment

[0022] Example 22-n-Butyl-3-(thiophenyl)benzofuran

[0023]

[0024] In a 25mL three-necked flask, add D-1 (220mg, 1mmol), then add Cs 2 CO 3 (652mg, 2mmol), diphenyl disulfide (109mg, 0.5mmol), L-proline (34.5mg, 0.3mmol), cuprous iodide (19mg, 0.1mmol), 1-hexyne (82mg, 1mmol), 5mL DMSO, under the protection of nitrogen, reacted in an oil bath at 90°C for 20h. After cooling, add 5mL water, and extract with 5mL ethyl acetate each time. After repeating four times, the extract was washed with saturated brine. The water was dried with sodium sulfate, filtered, and the liquid was distilled under reduced pressure. The distillate was separated by a silica gel column (the eluent was petroleum ether) to obtain 203.4 mg of a yellow viscous liquid with a yield of 72%.

[0025] 1 HNMR(500MHz, CDCl 3 )δ7.61(s,1H),7.44(s,1H),7.20(s,1H),7.19-7.16(m,3H),7.09-7.01(m,3H),2.94(s,2H),1.68 (s, 2H), 1.37 (s, 2H), 0.92 (s, 3H).

Example Embodiment

[0026] Example 32-(4-Methoxyphenyl)-3-(phenylthio)benzofuran

[0027]

[0028] In a 25mL three-necked flask, D-1 (220mg, 1mmol), then add K 2 CO 3 (276mg, 2mmol), diphenyl disulfide (109mg, 0.5mmol), L-proline (34.5mg, 0.3mmol), cuprous chloride (9.9mg, 0.1mmol), p-methoxyphenyl acetylene (132mg, 1mmol), 5mL DMSO, under the protection of nitrogen, reacted in an oil bath at 100°C for 20h. After cooling, add 5mL of water and extract with 5mL of ethyl acetate each time. After repeating four times, the extract is saturated with brine After washing, drying with anhydrous sodium sulfate, the filtered liquid was distilled under reduced pressure, and the distillate was separated through a silica gel column (the eluent was petroleum ether) to obtain 282.6 mg of a pale yellow viscous liquid with a yield of 85%.

[0029] 1HNMR(500MHz,CDCl3)δ7.54–7.46(m,4H), 7.36(t,J=7.5Hz,2H), 7.32–7.27(m,2H), 7.19(t,J=7.7Hz,2H), 7.14(s,1H), 7.10(t,J=7.3Hz,1H), 6.79(d,J=8.8Hz,2H), 3.75(s,3H).

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Abstract

The invention belongs to the technical field of organic chemical industry, and in particular, relates to a preparation method of a polysubstituted benzofuran derivative. The method is a coupling-tandem one-pot method, terminal alkyne, a halogenated phenol derivative and disulfide or diselenide undergo a reaction, amino acid is used as an additive, a copper salt is used as a catalyst, and under a condition of adding an alkali and in an organic solvent, a reaction is carried out to prepare the polysubstituted benzofuran derivative. An expensive palladium catalyst easily polluting the environment is not adopted, the reaction conditions are relatively mild, the process is simple, the operation is high, and the method has the prospect of industrial application.

Description

technical field [0001] The invention relates to the technical field of organic chemical industry, in particular to a preparation method of multi-substituted benzofuran derivatives. Background technique [0002] Benzofurans, an important class of heterocyclic compounds, widely exist in many biologically active compounds and natural products. They have been identified in the field of therapy as having anti-cancer, anti-tumor and immunosuppressive potentials, and are important intermediates for drug development and synthesis. Among them, 3-chalcogen-benzofuran is a very good skeleton structure, and more complex benzofuran derivatives can be prepared through 3-chalcogen-benzofuran. Therefore, it is of great significance to explore the synthesis method of 3-chalcogen-benzofuran compounds. Laroque and colleagues reported that using 2-(phenylethynyl)anisole and 4-NO 2 C 6 h 4 Synthesis of 3-chalcogen-benzofuran via electrophilic cyclization with SCl or PhSeCl. Through the cont...

Claims

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Application Information

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IPC IPC(8): C07D307/82
CPCC07D307/82
Inventor 刘烽张奕潘仙华
Owner 北京普诺旺康医药科技有限公司
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