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Method for tandem synthesis of dipyrrole and its derivatives through one-pot process

A technology for derivatives, dipyrrole, applied in the field of preparing dipyrrole and its derivatives, can solve the problems of difficult reaction conditions, high cost, long reaction route, etc. of raw materials, and achieves mild reaction conditions, good antibacterial activity, and good antitumor active effect

Inactive Publication Date: 2012-02-15
邱方利
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the simple and effective synthesis of 1,3′-dipyrrole derivatives from ready-made starting materials has not been reported yet; there are reports using microwave synthesis methods and other complex synthesis methods, which usually have long reaction routes and relatively high cost. High, and raw materials are not easy to obtain and harsh reaction conditions

Method used

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  • Method for tandem synthesis of dipyrrole and its derivatives through one-pot process
  • Method for tandem synthesis of dipyrrole and its derivatives through one-pot process
  • Method for tandem synthesis of dipyrrole and its derivatives through one-pot process

Examples

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Effect test

Embodiment 1

[0024] Under nitrogen protection, the raw material ethyl-2-cyano-3-ethoxypropene ester: TosMIC: NaH in molar ratio (1:1.2:1.3) was mixed and added to 10 mL of anhydrous CH 3 In CN, the reaction was stirred at room temperature for 12h, and the reaction was completed, and the reaction solution was washed with saturated NH 4 Cl solution to adjust the pH value to 7-8, then extract with dichloromethane 10mL×3, combine the organic layers, and wash with 10% Na 2 CO 3 The solution was washed with saturated brine, dried over anhydrous sodium sulfate, concentrated in vacuo, and purified by column chromatography to obtain the product 4-ethoxy-1'H-[1,3'-dipyrrole]-3,4'- Dinitrile, the product is a white solid, the yield is 53%.

Embodiment 2

[0026] Under nitrogen protection, the raw material ethyl-2-cyano-3-ethoxypropenyl ester:TosMIC:Cs 2 CO 3 According to the molar ratio (1:1.2:1.3) mixed into 10mL of anhydrous CH 3 In CN, the reaction was stirred at room temperature for 12h, and the reaction was completed, and the reaction solution was washed with saturated NH 4 Cl solution to adjust the pH value to 7-8, then extract with dichloromethane 10mL×3, combine the organic layers, and wash with 10% Na 2 CO 3 The solution was washed with saturated brine, dried over anhydrous sodium sulfate, concentrated in vacuo, and purified by column chromatography to obtain the product 4-ethoxy-1'H-[1,3'-dipyrrole]-3,4'- Dinitrile, the product is a white solid, the yield is 49%.

Embodiment 3

[0028] Under nitrogen protection, the raw material ethyl-2-cyano-3-ethoxypropenyl ester: TosMIC: K 2 CO 3 According to the molar ratio (1:1.2:1.3) mixed into 10mL of anhydrous CH 3 In CN, the reaction was stirred at room temperature for 12h, and the reaction was completed, and the reaction solution was washed with saturated NH 4 Cl solution to adjust the pH value to 7-8, then extract with dichloromethane 10mL×3, combine the organic layers, and wash with 10% Na 2 CO 3 The solution was washed with saturated brine, dried over anhydrous sodium sulfate, concentrated in vacuo, and purified by column chromatography to obtain the product 4-ethoxy-1'H-[1,3'-dipyrrole]-3,4'- Dinitrile, the product is a white solid, the yield is 28%.

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Abstract

The invention relates to a method for tandem synthesis of dipyrrole and its derivatives through a one-pot process. Dipyrrole and its derivatives have a structural formula as shown in formula (I). Dipyrrole and its derivatives are prepared in this way: trisubstituted alkene shown in formula (II) and isocyanide shown in formula (III) are taken as the main raw materials which react with the catalyst alkali at a certain temperature in an organic solvent so as to obtain the target product. The preparation method of dipyrrole and its derivatives in the invention has mild reaction conditions, and the products have good antibacterial activity and antitumor activity, wherein, the (I), (II) and (III) have the following structural formulas.

Description

technical field [0001] The invention relates to a method for synthesizing dipyrrole and its derivatives by a one-pot method in series, in particular to a method for preparing dipyrrole and its derivatives by using trisubstituted olefin and isonitrile as main raw materials. Background technique [0002] Pyrrole ring is one of the important heterocyclic compounds, and pyrrole and pyrrole derivatives are widely found in many natural products and drugs. In particular, dipyrrole has a moiety that is a synthetic precursor of various marine natural products, and a natural product containing an unusual 1,3′-dipyrrole-like moiety has been found to exhibit resistance to methicillin-resistant Staphylococcus aureus (MRSA) and human cancer cytotoxicity with strong antibacterial activity. [0003] p-Toluenesulfonic acid isonitrile (TosMIC) is a versatile synthon, which has been widely used in the synthesis of various heterocyclic compounds in organic chemistry, and the construction of py...

Claims

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Application Information

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IPC IPC(8): C07D207/416
Inventor 邱方利蒋华江黄国波葛昌华
Owner 邱方利
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