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2-(1-dimethylamino-2-cyanoethyl) pyrrole derivative and synthesis method thereof

A technology of pyrrole derivatives and synthetic methods, which is applied in the direction of organic chemistry, can solve the problems of high price, complicated preparation, and environmental pollution, and achieve the effects of simple operation, high yield, and high efficiency

Active Publication Date: 2020-06-16
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the traditional methods for preparing 2-alkylpyrrole derivatives mostly use copper (Tetrahedron 2008,64,10676.), zirconium (Org.Lett.2009,11,441.), scandium (Org.Lett.2006,8,2249 .) and other heavy metal catalysts, or small molecular compounds with special structures (J.Am.Chem.Soc.2001, 123, 4370.), there are disadvantages such as polluting the environment, expensive, complicated preparation, etc.

Method used

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  • 2-(1-dimethylamino-2-cyanoethyl) pyrrole derivative and synthesis method thereof
  • 2-(1-dimethylamino-2-cyanoethyl) pyrrole derivative and synthesis method thereof
  • 2-(1-dimethylamino-2-cyanoethyl) pyrrole derivative and synthesis method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030]

[0031] In a 10mL reaction flask, add N-methylpyrrole 2a (R 1 =CH 3 ; 2 =H) (41 mg, 0.5 mmol), 3-dimethylaminoacrylonitrile 3 (96 mg, 1.0 mmol), p-toluenesulfonic acid monohydrate (190 mg, 1.0 mmol) and 2 mL of solvent dichloromethane at 28 °C The reaction was stirred for 6h. After the reaction is completed, the reaction solution is poured into a separatory funnel, and 10 mL of saturated aqueous sodium bicarbonate solution is added thereto, shaken, left to stand, and the oil-water phase is separated, and the water phase is extracted with dichloromethane (2 × 5 mL), and the organic Mutually. The organic phases were combined, dried over anhydrous sodium sulfate, and filtered. The volatile components were removed, and then separated by silica gel column chromatography (the eluent was dichloromethane / ethyl acetate, v / v=50:1) to obtain the target product (1a) (75mg, yield 85% ). The target product was confirmed by NMR and high-resolution mass spectrometry.

[0032...

Embodiment 2

[0035] The reaction steps and operations are the same as those in Example 1, except that the reaction time is 1 h. The reaction was stopped, and the target product 1a (41 mg, yield 46%) was obtained after post-treatment.

Embodiment 3

[0037] The reaction steps and operations are the same as those in Example 1, except that the reaction time in the reaction is 24 hours. The reaction was stopped, and the target product 1a (74 mg, yield 84%) was obtained after post-treatment.

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Abstract

The invention discloses a 2-(1-dimethylamino-2-cyanoethyl)pyrrole derivative and a synthesis method thereof. According to the method, a pyrrole derivative which is cheap, easy to obtain and diverse instructure is used as a raw material and is subjected to a Friedel-Crafts reaction with 3-dimethylaminoacrylonitrile in the presence of acid to synthesize the 2-(1-dimethylamino-2-cyanoethyl) pyrrolederivative. The method has the advantages of cheap and accessible raw materials, low toxicity, mild synthesis reaction conditions and high efficiency, and is simple to operate.

Description

technical field [0001] The invention relates to a 2-(1-dimethylamino-2-cyanoethyl)pyrrole derivative and a method thereof, belonging to the technical field of chemical organic synthesis. Background technique [0002] 2-Alkylpyrrole derivatives are an important class of N-heterocyclic compounds, which not only have special biological activity (J.Med.Chem.1986,29,589.), but also can be used as organic intermediates for the preparation of other pyrrole Derivatives (Angew. Chem. Int. Ed. 2004, 43, 2293.). However, the traditional methods for preparing 2-alkylpyrrole derivatives mostly use copper (Tetrahedron 2008,64,10676.), zirconium (Org.Lett.2009,11,441.), scandium (Org.Lett.2006,8,2249 .) and other heavy metal catalysts, or small molecular compounds with special structures (J.Am.Chem.Soc.2001, 123, 4370.), there are disadvantages such as polluting the environment, expensive, and complicated preparation. Therefore, it is of great significance to develop effective synthetic ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/337
CPCC07D207/337
Inventor 余正坤吴凯凯
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI