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Three-component tandem synthesis method of multi-substituted pyrrole

A synthetic method and di-substitution technology, which is applied in the field of three-component tandem synthesis of 2-cyano-3-arylpyrrole compounds, can solve the problems of many by-products, cumbersome steps, and low product yields

Active Publication Date: 2017-12-22
LANZHOU UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, in the synthetic method of existing literature of this kind of compound, firstly, under the catalysis of boron trifluoride and trinitroiron nonahydrate, propargyl alcohol hexacarbonyl dicobalt complex reacts with 2-methylamino-acetonitrile to obtain 2-propargylamino-acetonitrile derivatives, and then prepared under the action of lithium diisopropylamide and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), the steps are cumbersome , many by-products, low product yield (Tetrahedron Lett.1995,36,2823)

Method used

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  • Three-component tandem synthesis method of multi-substituted pyrrole
  • Three-component tandem synthesis method of multi-substituted pyrrole
  • Three-component tandem synthesis method of multi-substituted pyrrole

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Experimental program
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Effect test

Embodiment

[0022] With N,N-dimethylformamide as both the reaction substrate and the reaction solvent, p-chlorostyrene is the aryl olefin substrate (reaction formula 1)

[0023]

[0024] Trimethylsilyl cyanide (240ul, 1.81mmol), copper trifluoromethanesulfonate (26mg, 0.072mmol), p-chlorostyrene (50mg, 0.36mmol) and DDQ (16mg, 0.072mmol) were sequentially added to the stirring In DMF (1mL), react at 80°C, add 16mg (0.072mmol) of DDQ every 2h for the first 8 hours of the reaction, and add 80mg (0.36mmol) of DDQ once at the 10th hour of reaction, and continue at 80°C Reaction 14h. After the reaction, the reaction system was extracted with ethyl acetate and washed with a saturated saline solution to obtain an organic phase, which was dried with anhydrous sodium sulfate for 0.5 h, and then the solvent was drained on a rotary evaporator. Finally, the spin-dried crude product was subjected to silica gel column chromatography. A white solid (67.3 mg, 86%) was obtained.

[0025] Product char...

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Abstract

The invention relates to a three-component tandem synthesis method of a 2-cyano-3-arylpyrrole compound, wherein the reaction general formula is defined in the specification. According to the present invention, N,N-disubstituted formamide, trimethylsilyl cyanide and aryl olefin or aryl alkyne are subjected to one-pot synthesis under the actions of a Lewis acid catalyst and an oxidizing agent to prepare the 2-cyano-3-arylpyrrole compound; the used starting raw materials are simple; excluding the final product, the intermediates during the tandem conversion do not require separation and purification so as to reduce the coat input and the labor force input; and the simple and efficient preparation method is provided for the 2-cyano-3-arylpyrrole and the derivative thereof.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a three-component serial synthesis method of 2-cyano-3-arylpyrrole compounds. Background technique [0002] Pyrrole heterocycles are an important class of chemical skeleton structures, which are widely used in organic synthetic chemistry, medicinal chemistry, and material chemistry. 2-cyano-3-arylpyrrole is an important class of pyrrole heterocyclic compounds. The cyano group and the substituent on the aromatic ring in this type of compound can make this kind of polysubstituted pyrrole compound undergo derivatization reaction, and then expand range of applications of these compounds. At present, in the synthetic method of existing literature of this kind of compound, firstly, under the catalysis of boron trifluoride and trinitroiron nonahydrate, propargyl alcohol hexacarbonyl dicobalt complex reacts with 2-methylamino-acetonitrile to obtain 2-propargylamin...

Claims

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Application Information

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IPC IPC(8): C07D207/34
CPCC07D207/34
Inventor 王少华牟学清彭蕊张帮红王杰
Owner LANZHOU UNIVERSITY
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