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Method for synthesizing multi-substituted pyrrole derivatives

A technology of pyrrole derivatives and synthetic methods, which is applied in the direction of organic chemistry, can solve problems such as increased synthesis costs and increased reaction safety risks, and achieve the effects of cost-saving synthesis, high yield, and strong practicability

Active Publication Date: 2018-03-20
南京医科大学康达学院
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

High temperature reaction not only greatly increases the synthesis cost, but also increases the safety risk of the reaction

Method used

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  • Method for synthesizing multi-substituted pyrrole derivatives
  • Method for synthesizing multi-substituted pyrrole derivatives
  • Method for synthesizing multi-substituted pyrrole derivatives

Examples

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Embodiment 1

[0031] Example 1, a method for synthesizing polysubstituted pyrrole derivatives, the structure of the polysubstituted pyrrole derivatives is as described in formula I, in formula I:

[0032] R substituting group is selected from hydrogen, alkyl, aryl;

[0033] R 1 , R 2 The substituting group is selected from hydrogen, halogen, alkyl, alkoxy, aryl;

[0034] R 3 The substituting group is selected from alkyl, alkoxy, arylamino;

[0035] The synthesis method uses aromatic primary amine derivatives shown in formula II, β-nitrostyrene and its derivatives shown in formula III, and 1,3-dicarbonyl compounds shown in formula IV as raw materials, and uses LAuCl and AgOTf as catalysts. , react at 20°C to generate the polysubstituted pyrrole derivatives described in formula I; the specific steps are as follows:

[0036] (1) In the reaction vessel, add an appropriate amount of catalysts LAuCl and AgOTf, then add an appropriate amount of reaction solvent, stir at room temperature, an...

Embodiment 2

[0040] Embodiment 2, a kind of synthesis method of polysubstituted pyrrole derivatives, this synthesis method is represented by aromatic primary amine derivative shown in formula II, β-nitrostyrene and its derivatives shown in formula III, 1 shown in formula IV , 3-dicarbonyl compound as raw material, using LAuCl and AgOTf as catalysts, reacting at 50°C to generate polysubstituted pyrrole derivatives described in formula I; the specific steps: aromatic primary amine derivatives shown in formula II, formula III The molar ratio of β-nitrostyrene and its derivatives and 1,3-dicarbonyl compound shown in formula IV is 1.1:1.2:1, and L in LAuCl is a ligand, which is 2-(di-tert-butyl Phosphine)biphenyl or 2-dicyclohexylphosphine-2,4,6-triisopropylbiphenyl; the reaction solvent is ethyl acetate, acetonitrile or toluene. All the other are identical with embodiment 1.

Embodiment 3

[0041] Embodiment 3, a kind of synthesis method of polysubstituted pyrrole derivatives, this synthesis method is represented by aromatic primary amine derivatives shown in formula II, β-nitrostyrene and its derivatives shown in formula III, 1 shown in formula IV , 3-dicarbonyl compound as raw material, using LAuCl and AgOTf as catalysts, reacting at 30°C to generate polysubstituted pyrrole derivatives described in formula I; the specific steps: aromatic primary amine derivatives shown in formula II, formula III The molar ratio of the β-nitrostyrene and its derivatives and the 1,3-dicarbonyl compound shown in Formula IV is 0.9:1.1:1, and L in LAuCl is a ligand, which is benzotriazole; Described reaction solvent is dichloromethane or methyl tert-butyl ether; All the other are identical with embodiment 1.

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Abstract

The invention relates to a synthetic method of multi-substituted pyrrole derivatives. The synthetic method adopts an aromatic primary amine derivative shown in formula II, beta-nitrostyrolene shown informula III and derivatives thereof and 1,3-dicarbonyl compound shown in formula IV as raw materials, and LAuCl and AgOTf as catalysts to react at 20 to 50 DEG C, thus obtaining the multi-substitutedpyrrole derivatives. According to the method, by selecting the catalysts, the reaction of the multi-substituted pyrrole derivatives at a low temperature and even at normal temperature is realized, the product yield is high, the practicability is high, the reaction condition is easy to control and implement, and the synthesis of the multi-substituted pyrrole derivatives is performed in a safer environment.

Description

technical field [0001] The invention relates to a method for synthesizing derivatives, in particular to a method for synthesizing polysubstituted pyrrole derivatives. Background technique [0002] Pyrrole and its homologues mainly exist in bone tar, and a small amount exists in coal tar. Pyrrole can be obtained by fractional distillation of bone tar; or treated with dilute alkali, acidified with acid and purified by fractional distillation. It is a five-membered heterocyclic compound containing a nitrogen heteroatom, and its molecular formula is C 4 h 5 N. [0003] Pyrrole derivatives have a wide range of anti-tumor, anti-inflammatory, antibacterial and other effects, so their research has been valued by people. In the prior art, the synthesis of multi-substituted pyrrole derivatives is carried out at high temperature, the general synthesis temperature is above 80°C, most of them reach 100°C, and even as high as 150°C. For example, Li Baole's "Multi-component One-pot Sy...

Claims

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Application Information

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IPC IPC(8): C07D207/416C07D207/333
CPCC07D207/333C07D207/416
Inventor 张明李莉安琼
Owner 南京医科大学康达学院
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