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Novel preparation method for polysubstituted 3-aminopyrrole

An aminopyrrole, multi-substituted technology, applied in the direction of organic chemistry and the like, can solve the problems of complex reaction steps, high industrial cost, harsh synthesis reaction conditions, etc., and achieve the effects of simple preparation, environmental friendliness, and mild reaction conditions.

Active Publication Date: 2019-07-02
甘肃森瀚石油科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0036] The technical problem to be solved by the present invention is to solve the problems of harsh synthesis reaction conditions, complicated reaction steps and high industrial cost in the above-mentioned prior art. The present invention provides a method for preparing a novel multi-substituted 3-aminopyrrole compound

Method used

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  • Novel preparation method for polysubstituted 3-aminopyrrole
  • Novel preparation method for polysubstituted 3-aminopyrrole
  • Novel preparation method for polysubstituted 3-aminopyrrole

Examples

Experimental program
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Effect test

Embodiment 1

[0050] Taking the synthesis of N-1,2-triphenyl-1H-pyrrol-3-amine with the following structural formula as an example, the specific method includes the following steps:

[0051]

[0052]Add 1,4-dioxane (2mL), compound Ia (0.3mmol), nitrosobenzene IIa (0.6mmol), I 2 (0.03mmol), H 2 O (0.6mmol), and stirred and reacted at 90°C for 12h, and the reaction process was monitored by thin-layer chromatography until the reaction was complete; the mobile phase of petroleum ether / ethyl acetate=100 / 1 was separated and purified by silica gel column chromatography to obtain polysubstituted 3-aminopyrrole compound IIIaa, the recovery rate was 74%. The reaction equation is as follows:

[0053]

[0054] The structure, NMR, and high-resolution mass spectrometry data of the resulting product are as follows:

[0055] 1H NMR (400MHz, CDCl3, ppm): δ=7.29-7.25(m,2H),7.23-7.15(m,6H),7.12-7.08(m,4H),6.90-6.89(m,3H),6.78 -6.74(m,1H),6.42-6.41(d,J=4.0 Hz,1H),5.23(s,1H);13C NMR(100MHz,CDCl3,ppm):...

Embodiment 2

[0057] Taking the synthesis of N,1-diphenyl-2-(o-tolyl)-1H-pyrrol-3-amine with the following structural formula as an example, the specific method includes the following steps:

[0058]

[0059] Add 1,4-dioxane (2mL), compound Ib (0.3mmol), nitrosobenzene IIa (0.6mmol), I 2 (0.03mmol), H 2 O (0.6mmol), and stirred and reacted at 90°C for 12h, and the reaction process was monitored by thin-layer chromatography until the reaction was complete; the mobile phase of petroleum ether / ethyl acetate=100 / 1 was separated and purified by silica gel column chromatography to obtain polysubstituted 3-aminofuran compound IIIba, the recovery rate is 73%. The reaction equation is as follows:

[0060]

[0061] The structure, NMR, and high-resolution mass spectrometry data of the resulting product are as follows: 1 H NMR (400MHz, CDCl 3 , ppm): δ=7.24-7.15(m,6H),7.13-7.09(m,2H),7.03-6.98(m,2H),6.89-6.85(m,4H),6.78-6.74(m,1H ),6.41-6.40(d,J=4.0Hz,1H),5.23(s,1H),2.28(s,1H); 13 C NMR (10...

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Abstract

The invention provides a novel method for synthesizing polysubstituted 3-aminopyrrole compounds under relatively-mild reaction conditions by utilizing high ynamine and nitrosobenzene as raw materials.The method provided by the invention uses the nitroso aromatic hydrocarbon as an amination reagent, the raw materials used in the method are simple to prepare, cheap and easy to obtain, and the method is simple to operate, and has a high yield and great industrial application value.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of multi-substituted 3-aminopyrrole compounds. Background technique [0002] 3-Aminopyrrole and its derivatives are an important class of heterocyclic compounds, which are the core structures of many natural compounds and have a wide range of applications in the fields of chemistry, medicine, biology, agriculture and materials. 3-aminopyrrole compounds can be transformed through various chemical reactions such as substitution reaction and cyclization reaction. They are important intermediates for the synthesis of carbocyclic and heterocyclic compounds, and have a wide range of applications in organic synthesis. Therefore, the methodological research on the synthesis of 3-aminopyrrole compounds has been paid close attention to by people. [0003] Traditional 3-aminopyrrole compound synthesis methods mainly contain two types: one is to ca...

Claims

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Application Information

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IPC IPC(8): C07D207/34
CPCC07D207/34
Inventor 严汝龙袁丙祥
Owner 甘肃森瀚石油科技有限公司
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