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Environmental-friendly preparation method of N-methyl-2-cyano-3-arylpyrrole compound

An arylpyrrole and compound technology, which is applied in the field of green preparation of N-methyl-2-cyano-3-arylpyrrole compounds, can solve the problems of low reaction efficiency, low atom utilization rate and the like, and achieves high reaction efficiency , The reaction conditions are environmentally friendly and green, and the effect of high reaction area selectivity

Active Publication Date: 2020-02-04
HUNAN UNIV OF SCI & ENG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] For the preparation method of N-methyl-2-cyano-3-arylpyrrole compound in the prior art, there are deficiencies such as low atom utilization rate, low reaction efficiency, low PMI (process quality intensity) index, etc., the present invention The purpose is to provide a method for N-methyl-2-cyano-3-arylpyrrole compounds with a new reaction mechanism, aiming to provide a method with high atomic efficiency, high yield, low cost, environmental friendliness, and no need for chromatography Purification, a new synthetic method that is beneficial to industrial production applications

Method used

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  • Environmental-friendly preparation method of N-methyl-2-cyano-3-arylpyrrole compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1～14

[0055] Following examples 1~14 all react by following reaction equation:

[0056]

[0057] The specific operation steps are: in a 50mL reaction tube, sequentially add terminal aryne (40mmol), trimethylnitrile silane (40mmol, 3.97g), N,N-dimethylformamide (40mmol, 2.93g), iodine ( 0.8 mmol, 1 g), the resulting mixture was stirred and reacted at 80°C for 2 hours. After the reaction, add 30ml of saturated sodium sulfite for washing, extract 3 times with 30mL of ethyl acetate, combine the extracts, concentrate the extracts in vacuo, dry in vacuo and calculate the weight.

Embodiment 1

[0059] raw material: Target product:

[0060] 1-methyl-3-phenyl-1H-pyrrole-2-carbonitrile:

[0061] Yield: 94%.

[0062] 1 H NMR (500MHz, CDCl 3 )δ7.69–7.65 (m, 2H), 7.41 (t, J = 7.7Hz, 2H), 7.31 (t, J = 7.4Hz, 1H), 6.83 (d, J = 2.6Hz, 1H), 6.41 ( d,J=2.7Hz,1H),3.81(s,3H).

[0063] 13 C NMR (126MHz, CDCl 3 )δ135.44, 132.97, 128.79, 127.96, 127.77, 126.66, 114.66, 108.34, 101.43, 35.65.

Embodiment 2

[0065] raw material: Target product:

[0066] 1-methyl-3-(p-tolyl)-1H-pyrrole-2-carbonitrile:

[0067] Yield: 95%.

[0068] 1 H NMR (500MHz, CDCl 3 )δ7.57(d, J=8.0Hz, 2H), 7.22(d, J=7.8Hz, 2H), 6.82(d, J=2.4Hz, 1H), 6.39(d, J=2.5Hz, 1H) ,3.80(s,3H),2.37(s,3H).

[0069] 13 C NMR (126MHz, CDCl 3 )δ137.65, 135.56, 130.13, 129.69, 127.89, 126.56, 114.78, 108.18, 101.25, 35.61, 21.35.

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Abstract

The invention discloses an environmental-friendly preparation method of N-methyl-2-cyano-3-arylpyrrole compound. The environmental-friendly preparation method includes the steps that terminal aromaticalkynes, trimethylsilyl cyanide, N,N-dimethylformamide with the same chemical molar amount are subjected to a three-component addition reaction under the catalysis of molecular iodine to generate theN-methyl-2-cyano-3-arylpyrrole compound; and after the reaction is completed, a reaction system is washed by saturated sodium sulfite, a water phase is extracted by ethyl acetate, and the N-methyl-2-cyano-3-arylpyrrole compound with high purity can be obtained. The preparation method is good in product selectivity, high in yield, simple in separation process, low in cost of catalysts, environmental-friendly, and is conducive to industrial production and application.

Description

technical field [0001] The invention belongs to the technical field of organic intermediate synthesis, and in particular relates to a green preparation method of N-methyl-2-cyano-3-arylpyrrole compound. Background technique [0002] Pyrrole compounds are an important class of five-membered nitrogen-containing heterocyclic compounds, and are commonly used pharmacophore in the field of drug research. The derivatives of the parent structure have various physiological and pharmacological activities, and are widely used as anticancer drugs, antitumor drugs Drugs, antibacterial drugs, etc., are a class of potential multi-purpose lead compounds with broad development and application prospects. [0003] The cyano group is a carbon-nitrogen triple bond with strong polarity. It is small in size, only 1 / 8 of the methyl group, and has a strong electron-withdrawing property. In addition, it also has a good hydrogen bond acceptor, and can interact with carbonyl , halogen and other functi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/34C07D401/04C07D409/04
CPCC07D207/34C07D401/04C07D409/04
Inventor 王峥丁满花王毅
Owner HUNAN UNIV OF SCI & ENG
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