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Method for preparing polysubstituted thiophene

A multi-substitution and thiophene technology, applied in organic chemistry and other fields, can solve problems such as rare literature

Inactive Publication Date: 2020-08-21
LANZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In addition, various fluorine groups (such as SCF 3 , CF 3 ) is particularly attractive for introduction into thiophene, a method rarely seen in the literature

Method used

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  • Method for preparing polysubstituted thiophene
  • Method for preparing polysubstituted thiophene
  • Method for preparing polysubstituted thiophene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] The reaction formula of embodiment 1, the specific raw material compound A-1 and B-1 used and the structure of product I-1 are as follows

[0020]

[0021] The specific experimental steps are: 127mg (0.45mmol, 1.5eq) of compound A-1 and 56mg (0.3mmol, 1.0eq) of compound B-1 were dissolved in 3mL of dichloroethane and reacted at 85°C. Reaction monitoring B-1 disappeared completely, and the reaction was completed, and the reaction mixture was rotary-evaporated under the reduced pressure of the water pump to remove the solvent dichloroethane. The residue was chromatographed on a 200-300 mesh silica gel column to obtain the compound shown in I-1, and the product was identified by NMR (hydrogen spectrum, carbon spectrum) and high-resolution mass spectrometry.

[0022] Product Ⅰ-1 was a yellow oil with a yield of 81%. 1 H NMR (400MHz, CDCl 3 )δ7.79(d, J=7.3Hz, 2H), 7.60(t, J=7.4Hz, 1H), 7.46(t, J=7.7Hz, 2H), 3.95(s, 3H), 3.69(s, 3H), 3.68(s, 3H); 13 CNMR (100MHz, CDCl ...

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Abstract

The invention belongs to the technical field of chemical synthesis, and particularly relates to a method for preparing polysubstituted thiophene, which is simple to operate, green, environment-friendly, high in yield and suitable for large-scale preparation. According to the method, sulfur-containing ylide and electron-deficient alkyne are used as initial raw materials, and tetra-substituted and tri-substituted thiophene, especially fluorinated thiophene, are prepared in dichloroethane without other catalysts or metal reagents under the condition of heating.

Description

technical field [0001] The application belongs to the technical field of chemical synthesis, and in particular relates to a method for preparing multi-substituted thiophenes. Background technique [0002] As we all know, thiophene, as a class of sulfur-containing five-membered heterocyclic rings, is widely distributed in natural products, drug molecules and functional materials, and is often used as an important synthetic intermediate in organic chemistry and materials chemistry. Therefore, organic chemists have been devoting themselves to developing efficient methods to construct such unique heterocycles. However, there are limited methods for synthesizing polysubstituted thiophenes, many of which involve metal catalysts, malodorous starting materials, or harsh reaction conditions. Furthermore, for pharmaceutical and materials chemistry, metal contamination in products is always a problem. In addition, various fluorine groups (such as SCF 3 , CF 3 ) into thiophene is pa...

Claims

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Application Information

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IPC IPC(8): C07D333/38C07D409/06
CPCC07D333/38C07D409/06
Inventor 程斌李运通翟宏斌张昕平李慧胡汉巍
Owner LANZHOU UNIVERSITY
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