Production method of 2,5-diaryl-3-cyanopyrrole compound

A cyanopyrrole and compound technology, which is applied in the field of preparation of 2,5-diaryl-3-cyanopyrrole compounds, can solve the problems such as the difficulty in obtaining ketone compounds, and achieves overcoming the difficulty in obtaining raw materials, novel synthesis methods, and the like. high yield effect

Active Publication Date: 2019-12-03
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this reaction has the disadvantages that the raw material 2-cyano-1,4-diketone compound is not easy to obtain, etc.

Method used

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  • Production method of 2,5-diaryl-3-cyanopyrrole compound
  • Production method of 2,5-diaryl-3-cyanopyrrole compound
  • Production method of 2,5-diaryl-3-cyanopyrrole compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Example 1, 2-p-tolyl-3-cyano-5-phenylpyrrole (m1)

[0023] Add 184mg (1.0mmol) of 2-phenylacetylmalononitrile, 204mg (1.5mmol) of p-tolueneboronic acid, 44.8mg (0.2mmol) of palladium acetate, and 15.0ml of toluene into a 50ml three-necked flask, and heat up to 100°C under stirring to react for 24 After 1 hour, the reaction was detected by TLC (petroleum ether:ethyl acetate=5:1 volume ratio, when the complete disappearance of the raw material 2-phenylacetylmalononitrile was detected, the reaction was judged to be complete).

[0024] After the reaction, the resulting reaction solution was suction filtered through diatomaceous earth, concentrated by a rotary evaporator (evaporating temperature of 40°C) to remove toluene, and concentrated liquid column chromatography (petroleum ether: ethyl acetate = 20:1 volume ratio) 222.2 mg of the product 2-p-tolyl-3-cyano-5-phenylpyrrole was obtained with a yield of 86%.

[0025] The column chromatography is specifically as follows: p...

Embodiment 2

[0044] Example 2, 2,5-di-p-tolyl-3-cyanopyrrole (m2)

[0045] Replace 2-phenylacetylmalononitrile with 2-p-methylphenylacetylmalononitrile, the molar weight remains unchanged, and the rest are equal to Example 1. 227.7 mg of the white solid product 2,5-xylyl-3-cyanopyrrole was obtained, with a yield of 84% and a purity of 97%.

[0046] Its structural formula is:

[0047]

[0048] White solid; mp:197.3-198.0℃; 1 H NMR (500MHz, DMSO-d 6 )δ12.06(s,1H),7.74(d,J=8.5Hz,2H),7.70(d,J=8.0Hz,2H),7.35(d,J=8.0Hz,2H),7.24(d, J=8.0Hz, 2H), 6.98(d, J=2.5Hz, 1H), 2.37(s, 3H), 2.32(s, 3H); HRMS(ESI): m / z calcd for C 19 h 17 N 2 [M+H] + :273.1386,found:273.1389.

Embodiment 3

[0049] Example 3, 2,5-diphenyl-3-cyanopyrrole (m3)

[0050] Replace p-tolueneboronic acid with phenylboronic acid, the molar weight is constant, and all the other are the same as in Example 1. 205.4 mg of the white solid product 2,5-diphenyl-3-cyanopyrrole was obtained, with a yield of 84% and a purity of 97%.

[0051] Its structural formula is:

[0052]

[0053] White solid; mp:206.1-206.8℃; 1 H NMR (500MHz, DMSO-d 6 )δ12.21(s,1H),7.85(d,J=7.5Hz,2H),7.82(d,J=7.0Hz,2H),7.56(t,J=8.0Hz,2H),7.48–7.40( m,3H),7.31(t,J=7.0Hz,1H),7.09(d,J=2.5Hz,1H); HRMS(ESI):m / z calcd for C 17 h 13 N 2 [M+H] + :245.1073,found:245.1074.

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Abstract

The invention discloses a production method of a 2,5-diaryl-3-cyanopyrrole compound. The production method of the 2,5-diaryl-3-cyanopyrrole compound comprises the following steps: in a solvent, undercatalysis of palladium acetate, subjecting a 2-phenylacetyl malononitrile compound and a substituent phenylboronic acid compound to a reaction, wherein reaction temperature is 95-105 DEG C, and reaction time is 20-30 hours; and conducting post-treatment on obtained reaction liquid to obtain the 2,5-diaryl-3-cyanopyrrole compound. According to the production method of the 2,5-diaryl-3-cyanopyrrolecompound, the raw materials which are easy to obtain are used, and through the cascade reaction, not only is a pyrrole ring built through cyclization, but also two aryl groups are introduced onto a 2,5- site, so that the 2,5-diaryl-3-cyanopyrrole compound is obtained.

Description

technical field [0001] The present invention relates to a preparation method of 2,5-diaryl-3-cyanopyrrole compound, that is, 2-phenylacetylmalononitrile compound reacts with substituted phenylboronic acid compound under the catalysis of palladium acetate to obtain 2, 5-Diaryl-3-cyanopyrrole compounds. Background technique [0002] Pyrrole derivatives are an important class of five-membered nitrogen heterocyclic compounds, and widely exist in natural products and biologically active molecules, such as heme, chlorophyll, bile pigments, certain amino acids, certain alkaloids and the basic structure of some enzymes unit. Pyrrole derivatives show a variety of biological activities, including antioxidant activity, amine oxidase inhibitory activity, antibacterial, antitumor and anti-inflammation, etc., so they are widely used in medicine, pesticides, food, daily chemicals, coatings, Textile and many other aspects. [0003] Pyrroles are usually synthesized by the condensation rea...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/34
CPCC07D207/34
Inventor 章国林王紫娟俞永平
Owner ZHEJIANG UNIV
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