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A microwave radiation-assisted synthesis method of n-methyl-2-cyano-3,4-disubstituted pyrrole compound

A technology of disubstituted pyrrole and trimethylcyanosilane, which is applied in the field of organic intermediate synthesis, can solve the problems of low reaction efficiency, low atom utilization rate, and cannot be applied in industry, and achieves simple reaction conditions, environmental protection and green reaction conditions. , the effect of improving atomic utilization and efficiency

Active Publication Date: 2021-04-23
HUNAN UNIV OF SCI & ENG
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0006] In view of the lack of one-step synthesis of N-methyl-2-cyano-3,4-disubstituted pyrrole compounds in the prior art, the few technologies still have low atom utilization rate, low reaction efficiency, and cannot be applied industrially and other deficiencies, the purpose of the present invention is to provide a kind of N-methyl-2-cyano-3,4-disubstituted pyrrole compound microwave radiation-assisted synthesis method of a new reaction mechanism, aiming to provide a High atomic efficiency, high yield, low cost, no need for chromatographic purification, and a new synthetic method that is conducive to industrial production and application

Method used

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  • A microwave radiation-assisted synthesis method of n-methyl-2-cyano-3,4-disubstituted pyrrole compound
  • A microwave radiation-assisted synthesis method of n-methyl-2-cyano-3,4-disubstituted pyrrole compound
  • A microwave radiation-assisted synthesis method of n-methyl-2-cyano-3,4-disubstituted pyrrole compound

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Effect test

Embodiment 1～3

[0051]The following Examples 1 to 3 are reacted in the following reaction equation:

[0052]

[0053]The specific steps are: in a 50 ml round bottom flask, an alkyne (30 mmol), trimethylthilane (30 mmol, 2.97 g), N, N-dimethylformamide (30 mmol, 2.19 g), iodine Sodium (3 mmol, 0.45 g), the resulting mixture was stirred at 300 W in the microwave reactor, and the reaction was stirred at 10 ° C for 10 minutes. After completion of the reaction, 30 ml of ethyl acetate was dissolved, saturated brine wash solution, dispensing, and concentrated in vacuo, vacuum drying calculation weight.

Embodiment 1

[0055]raw material:Target product:

[0056]1, 4-Dimethyl-3-Phenyl-1H-Pyrrole-2-Carbonitrile:

[0057]Yield: 92%.

[0058]1H NMR (500MHz, CDCL3: 7.50-7.44 (m, 4H), 7.39-7.34 (m, 1H), 6.88 (S, 1H), 5.32 (S, 1H), 3.78 (S, 3H), 2.14 (S, 3H).

[0059]13C NMR (125MHz, CDCL3: 134.6, 132.9, 128.6, 128.6, 127.3, 126.6, 118.1, 114.34, 53.4, 35.2, 10.7.

[0060]HRMS (ESI) Calcd for C13Hide13N2[M + h]+: 197.1079, Found 107.1081.

Embodiment 2

[0062]raw material:Target product:

[0063]Yield: 93%.

[0064]1-Methyl-3,4-Diphenyl-1H-Pyrrole-2-Carbonitrile

[0065]1H NMR (500MHz, CDCL3Δ7.35-7.27 (m, 5H), 7.26-7.22 (m, 3H), 7.18-7.13 (m, 2H), 6.92 (S, 1H), 3.85 (S, 3H).

[0066]13C NMR (125MHz, CDCL3Δ133.7, 133.4, 132.4, 129.3, 128.7, 128.6, 128.5, 127.7, 126.7, 126.4, 124.5, 114.3, 104.3, 35.7.

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Abstract

The invention discloses a microwave radiation-assisted synthesis method of N-methyl-2-cyano-3,4-disubstituted pyrrole compound, in which alkyne, trimethylcyanosilane, N,N ‑Dimethylformamide, catalyzed by sodium iodide and assisted by microwaves to carry out a one-pot reaction to generate N‑methyl‑2‑cyano‑3,4‑disubstituted pyrrole compounds. The method has good product selectivity, high yield, simple separation process, low catalyst cost, environmental friendliness, and is beneficial to industrial production and application.

Description

Technical field[0001]The present invention belongs to the field of organic intermediate synthesis, and more particularly to a microwave radiation auxiliary synthesis method of N-methyl-2-cyano-3,4-bis substituted pyrrole compound.Background technique[0002]The pyrrole compound is an important type of nitrogen-containing heterocyclic compound, which is a commonly used pharmacodynamic group in the field of pharmaceutical studies. The mother structure has a variety of physiological, pharmacological activity, widely used as an anti-cancer drug, anti-tumor Drugs, antibacterial drugs, etc. are a class of potential multi-purpose lead compounds with a wide range of development and application prospects.[0003]Group modification of pyrrole loops is possible to obtain a drug having better potential efficacy. For example, the cyano group has special properties, and the cyano-modified to the pyrrole loop structure is likely to obtain a pharmaceutical intermediate having a variety of potential eff...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D207/34
CPCC07D207/34
Inventor 龚绍峰包文虎丁满花
Owner HUNAN UNIV OF SCI & ENG
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