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2-amino-4-acylpyrrole compound and production method thereof

An acylpyrrole and compound technology, which is applied in the field of 2-amino-4-acylpyrrole compounds and their preparation, can solve problems such as complicated synthesis of raw materials, and achieve the effects of simple method and wide applicability of substrates

Active Publication Date: 2019-10-25
JIAXING UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although the reaction is efficient, the synthesis of raw materials is cumbersome

Method used

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  • 2-amino-4-acylpyrrole compound and production method thereof
  • 2-amino-4-acylpyrrole compound and production method thereof
  • 2-amino-4-acylpyrrole compound and production method thereof

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preparation example Construction

[0034] The present invention provides the preparation method of the 2-amino-4-acylpyrrole compound described in the above technical scheme, comprising the following steps:

[0035] Mixing arylamine, alkynyl ketone, tert-butyl isocyanide, acetate, catalyst and organic solvent for a synthesis reaction to obtain 2-amino-4-acylpyrrole compound;

[0036] The arylamine has a structure shown in formula II;

[0037]

[0038] The alkynyl ketone has a structure shown in formula III:

[0039]

[0040] Among them, R 1 is -H, a halogen group, a methoxy group or a methyl group; R 2 is aryl, butyl or hydrogen; R 3 is aryl, trifluoromethyl or hydrogen.

[0041] In the present invention, the aromatic amine preferably includes aniline, N,N-dimethyl-4-aminoaniline, 2-iodoaniline, p-methylaniline, 4-chloroaniline, 4-methoxyaniline. In the present invention, the alkynyl ketone preferably includes phenylpropynyl formaldehyde, p-chlorophenylpropynyl formaldehyde, 2-thienylpropynyl formald...

Embodiment 1

[0050] Aniline (1a, 0.10M), phenylpropynylcarbaldehyde (2a, 0.12M), tert-butylisocyanate (0.3M), KOAc (1M) and palladium acetate (the molar percentage of palladium acetate and aniline is 5% ) was added into acetonitrile and mixed, the resulting reaction solution was heated to 80° C., and the synthesis reaction was carried out for 10 h, the resulting reaction solution was filtered, and the resulting filtrate was separated by column chromatography to obtain N-phenyl-2-amino-4-acylpyrrole ( 4a); the separation yield is 78%; the recorded concentration is the concentration of each raw material in the reaction solution; the synthetic reaction equation of embodiment 1 is as follows:

[0051]

[0052] 1 H NMR (500MHz, CDCl 3 )δ7.43-7.33 (m, 6H), 7.31 (d, J = 7.0Hz, 1H), 7.27 (d, J = 13.0Hz, 3H), 2.42 (s, 3H), 2.09 (s, 3H), 1.51(s, 9H), 0.55(s, 9H); 13 C NMR (126MHz, CDCl 3 )δ170.2, 169.2, 137.7, 136.6, 136.4, 134.6, 130.1, 129.7, 128.2, 127.6, 126.8, 125.6, 120.7, 120.3, 57.7, ...

Embodiment 2

[0054]N,N-dimethyl-4-aminoaniline (1b, 0.10M), p-chlorophenylpropynyl formaldehyde (2b, 0.12M), tert-butylisocyanate (0.3M), KOAc (1M) and palladium acetate (The molar percentage of palladium acetate and N, N-dimethyl-4-aminoaniline is 10%) was added to 1,2-dichloroethane and mixed, and the resulting reaction solution was heated to 80°C to carry out the synthesis reaction After 10h, the obtained reaction solution was filtered, and the obtained filtrate was separated by column chromatography to obtain N-(4-(N,N-dimethyl)amino)phenyl-2-amino-4-acylpyrrole (4b). The rate is 82%; the recorded concentration is the concentration of each raw material in the reaction solution; the synthetic reaction equation of embodiment 2 is as follows:

[0055]

[0056] 1 H NMR (500MHz, CDCl 3 )δ7-38-7.35(m, 2H), 7.33-7.30(m, 2H), 7.26(d, J=7.0Hz, 2H), 7.22(s, 1H), 6.76(d, J=9.0Hz, 2H ), 3.02(s, 6H), 2.07(s, 3H), 1.50(s, 9H), 0.59(s, 9H); 13 C NMR (126MHz, CDCl 3 C 29 h 37 ClN 4 o 2 508...

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Abstract

The invention belongs to the technical field of organic synthesis, and particularly relates to a 2-amino-4-acylpyrrole compound and a production method thereof. The provided 2-amino-4-acylpyrrole compound is novel in structure; no strong acids are used in the provided production method, and reaction conditions are mild; and arylamine, alkynyl ketone, isocyan and acetate which are simple and easy to obtain are used as raw materials, and the 2-amino-4-acylpyrrole compound is synthesized in one step, so that the method is concise, fast and wide in substrate applicability.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a 2-amino-4-acylpyrrole compound and a preparation method thereof. Background technique [0002] 2-Aminopyrrole is an important class of heterocyclic compounds existing in nature, and many drugs or drug intermediates contain 2-aminopyrrole structural units. More and more studies have shown that isoquinolinone derivatives have pharmacological activities such as anti-inflammatory, analgesic, anti-tumor and anti-bacterial fungi. Such as: Pyrronitrin has good antibacterial activity. [0003] In 2009, the French Zhu Jieping group reported the use of α, β-unsaturated imines as raw materials, using AlCl 3 The promoted reaction synthesized 2-amino-5-cyanopyrroles (Synthesis of Pyrroles by Consecutive Multicomponent Reaction / [4+1]Cycloaddition of Iminonitriles with Isocyanides, Organic Letters, 2009, 11, 1555). Although this reaction is highly efficient, the synthesis of star...

Claims

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Application Information

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IPC IPC(8): C07D207/34C07D409/04
CPCC07D207/34C07D409/04
Inventor 邱观音生陈佃鹏张雅晶
Owner JIAXING UNIV
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