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Preparation method of pyrrole derivatives

A technology of pyrrole derivatives and pyrrole, applied in the direction of organic chemistry, etc., can solve the problems of difficult industrialized production, long reaction time, low yield and the like

Active Publication Date: 2016-05-11
临沂市高新汽车租赁服务有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Chem.Comm., 2013, 49, 5073 reported a method for constructing pyrrole structure by cycloaddition, but there are disadvantages such as low yield and long reaction time, so it is difficult to apply to industrial production; CryEngComm, 2014, 16, 10485 A novel organometallic framework material with the molecular formula C 3 h 8 AgN 7 It is a silver-azotetrazole structure, and it is used to degrade organic dyes, but its application in other fields has not been reported further

Method used

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  • Preparation method of pyrrole derivatives
  • Preparation method of pyrrole derivatives
  • Preparation method of pyrrole derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021]

[0022] Add 5mol% (relative to the alkyne) silver azotetrazole catalyst C in sequence in a 20ml flask 3 h 8 AgN 7 , then add 20mmol methylene aziridine and 10mmol alkyne, add 10ml toluene, and finally react at room temperature 25°C for 2h. After the reaction was completed, the reaction was filtered, the solvent was concentrated and evaporated by a rotary evaporator, the solid was subjected to silica gel column chromatography, and the column was washed with an eluent of petroleum ether:ethyl acetate=20:1 to obtain the target pyrrole compound with a yield of 90%. Purity≥99%.

Embodiment 2

[0024]

[0025] Add 4 mol% (relative to the alkyne) silver azotetrazole catalyst C in a 20ml flask 3 h 8 AgN 7 , Then add 20mmol methylene aziridine and 10mmol alkyne, add 10ml toluene, and finally react at room temperature 25°C for 5h. After the reaction was completed, it was filtered, and the solvent was concentrated and evaporated by a rotary evaporator. The solid was subjected to silica gel column chromatography, and the column was washed with an eluent of petroleum ether:ethyl acetate=20:1 to obtain the target pyrrole compound with a yield of 92%. Purity≥99%.

Embodiment 3

[0027]

[0028] Add 3 mol% (relative to the alkyne) silver azotetrazole catalyst C in a 20ml flask 3 h 8 AgN 7 , Then add 20mmol methylene aziridine and 15mmol alkyne, add 15ml toluene, and finally react at room temperature 25°C for 6h. After the reaction was completed, it was filtered, and the solvent was concentrated and evaporated by a rotary evaporator. The solid was subjected to silica gel column chromatography, and the column was washed with an eluent of petroleum ether:ethyl acetate=20:1 to obtain the target pyrrole compound with a yield of 92%. Purity≥99%.

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Abstract

The invention relates to a method for efficient construction of a pyrrole ring structure; a silver azo metal framework material is used as a catalyst, methylene aziridines I and alkynyl compounds II are subjected to a cycloaddition reaction, and a series of pyrrole compounds III are synthesized; the preparation method has the advantages of higher yield, fast reaction, mild conditions and easy industrialization.

Description

technical field [0001] The present invention relates to a method for preparing pyrrole derivatives. The specific method is to prepare substituted pyrrole derivatives through [3+2] cycloaddition reaction between methylene aziridine and alkyne, using silver-azotetrazole metal organic framework material as a catalyst. Background technique [0002] Pyrrole and its derivatives are one of the important heterocyclic compounds in medicinal chemistry. This type of structure widely exists in natural products and some artificially synthesized compounds with biological activity, such as porphyrin and vitamin B12. The construction of pyrrole rings has been used in the synthesis of many active drug molecules, such as the antifungal drug pyrrolnitrine, the antibacterial drug statamycin, the anti-inflammatory drug tolmetin, and the antitumor drug vincristine, etc. It can be seen that the construction of pyrrole ring is a very useful module in organic synthesis, and the construction of pyrr...

Claims

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Application Information

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IPC IPC(8): C07D207/323C07D207/46C07D207/333C07D207/325
CPCC07D207/323C07D207/325C07D207/333C07D207/46
Inventor 刘丽蓉
Owner 临沂市高新汽车租赁服务有限公司
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