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Multi-substituted n-arylpyrrole compound and its preparation method

A technology for aryl pyrroles and dicarbonyl compounds is applied in the field of polysubstituted N-aryl pyrroles and their synthesis, and achieves the effects of good reaction selectivity, high industrial application value and high yield

Active Publication Date: 2022-03-22
HUBEI BIOPESTICIDE ENG RES CENT
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these existing methods for synthesizing multi-substituted pyrroles often have disadvantages such as substrate pre-functionalization, high temperature and pressure, and noble metal catalysis. Therefore, it is urgent to find a synthetic method with cheap and easy-to-obtain substrates, good reaction selectivity, and low economic cost. method

Method used

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  • Multi-substituted n-arylpyrrole compound and its preparation method
  • Multi-substituted n-arylpyrrole compound and its preparation method
  • Multi-substituted n-arylpyrrole compound and its preparation method

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] The structural formula of the partially multi-substituted N-arylpyrrole compound of the present invention is as the specific structure listed below, but is not limited to the structure listed in the following examples:

[0025]

Embodiment 2

[0027] The compound numbered as 4a in embodiment 1 is prepared, and its reaction formula is:

[0028]

[0029] During the specific preparation, aniline (0.5mmol), bromoacetaldehyde diethyl acetal (0.5mmol) and acetylacetone (0.5mmol) were dissolved in the organic solvent toluene (2mL) respectively, and then the catalyst iron trichloride (0.05mmol) was added. , the above reaction solution was stirred and reacted at 60° C. for 6 hours in a reactor equipped with magnetic stirring. Concentrate under reduced pressure after reaction finishes, carry out silica gel column chromatography (V 石油醚 :V 乙酸乙酯 =20: 1), the purified product 4a was 51.76 mg, and the isolated yield was 52%. The obtained spectral data of 4a are as follows:

[0030] 1 H NMR (600MHz, CDCl 3 ,TMS,25℃)δ=7.50–7.46(m,2H),7.44–7.41(m,1H),7.28–7.26(m,2H),6.68(d,J=3.1Hz,1H),6.62(d ,J=3.1Hz, 1H), 2.46(s,3H), 2.46(s,3H)ppm. 13 C NMR (150MHz, CDCl 3 ,25℃) δ= 195.4, 139.0, 135.7, 129.5, 128.3, 126.4, 122.1, 121.3, 1...

Embodiment 3

[0032] The compound numbered as 4b in embodiment 1 is prepared, and its reaction formula is:

[0033]

[0034] During the specific preparation, aniline (0.5mmol), bromoacetaldehyde diethyl acetal (1.0mmol) and methyl acetoacetate (0.5mmol) were dissolved in the organic solvent 1,2-dichloroethane (2mL) respectively, and then added The catalyst is aluminum trichloride (0.10 mmol), and the reaction solution is stirred and reacted at 80° C. for 4 hours in a reactor equipped with magnetic stirring. Concentrate under reduced pressure after reaction finishes, carry out silica gel column chromatography (V 石油醚 :V 乙酸乙酯 =10:1), the purified product 4b was 72.05 mg. The isolated yield was 67%. The resulting spectral data for 4b are as follows:

[0035] 1 H NMR (600MHz, CDCl 3 ,TMS,25℃)δ=7.49–7.46(m,2H),7.43–7.40(m,1H),7.28–7.26(m,2H),6.67(d,J=3.1Hz,1H),6.65(d ,J=3.1Hz, 1H), 3.83(s,3H), 2.44(s,3H)ppm. 13 C NMR (150MHz, CDCl 3 , 25°C) δ=166.0, 139.2, 136.2, 129.3, 128.0, 126.3, ...

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Abstract

The invention provides a multi-substituted N-arylpyrrole compound and a preparation method thereof. Its structure is: the preparation method uses aromatic amine, bromoacetaldehyde diethyl acetal, and 1,3-dicarbonyl compound as raw materials in an organic solvent and synthesized under catalytic conditions. The compound has a novel structure and has active sites such as ester groups and carboxyl groups, which is conducive to further structural optimization and the development of pyrrole compounds with important antibacterial, insecticidal and antiviral activities. At the same time, the raw materials used in the preparation method of the present invention are cheap and easy to obtain, the operation is simple, and the industrial application value is great.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and more specifically relates to a multi-substituted N-arylpyrrole compound and a synthesis method thereof. Background technique [0002] Pyrrole alkaloids are a very important class of compounds in the research of medicinal chemistry and natural product chemistry. As an important nitrogen-containing five-membered heterocyclic ring, pyrrole alkaloids have a wide range of biological and pharmacological activities. They are many natural products and drug molecules. The core skeleton structure of pyrrole compounds plays a key role in antibacterial, insecticidal, antiviral, anticancer and other fields. The following formula lists several representative drugs and natural product molecules containing pyrrole units. [0003] [0004] Due to the unique biological activity of polysubstituted pyrrole compounds and their wide application in medicine and natural products, the synthesis and preparation of ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D207/34C07D401/04
CPCC07D207/34C07D401/04
Inventor 黄文博柯少勇王开梅方伟万中义
Owner HUBEI BIOPESTICIDE ENG RES CENT