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Method for synthesizing substituted pyrrole by cycloaddition reaction of 1, 3-diyne and primary amine

A technology of cycloaddition and amine compounds, which is applied in the direction of organic chemistry, can solve the problems of harsh reaction conditions, low yield, long reaction time, etc., and achieve the effects of high-efficiency reaction, simple reaction operation and high chemical reactivity

Inactive Publication Date: 2011-01-19
TSINGHUA UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] In summary, the new catalytic reaction system for the one-step synthesis of pyrrole compounds is one of the focuses of people's attention, but many of the current new methods still have many shortcomings, such as the need for many processing steps, the need to synthesize precursors first, and harsh reactions. Conditions, very low yield, long reaction time, etc., so the new catalytic reaction system with high chemical reactivity, cheap catalyst system and practical needs further research and development

Method used

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  • Method for synthesizing substituted pyrrole by cycloaddition reaction of 1, 3-diyne and primary amine
  • Method for synthesizing substituted pyrrole by cycloaddition reaction of 1, 3-diyne and primary amine
  • Method for synthesizing substituted pyrrole by cycloaddition reaction of 1, 3-diyne and primary amine

Examples

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Embodiment 1

[0025] Weigh 5 mg (0.05 mmol) of CuCl and 101.0 mg (0.5 mmol) of 1,3-diphenyldiyne into a 25-mL glass reaction tube with a cover, replace the air in the reaction tube with nitrogen, and add 0.5mL of aniline, then seal the reaction tube, place the reaction tube in an oil bath and heat to 100°C, stir and keep warm for 24 hours, then cool to room temperature to obtain the target product 1,2,5-triphenylpyrrole provided by the present invention. Reaction result: the isolated target product 1,2,5-triphenylpyrrole was weighed, and the isolated yield of the product was calculated to be 96%. figure 1 and figure 2 The hydrogen spectrum and carbon spectrum of the target product 1,2,5-triphenylpyrrole prepared in this example are shown respectively. It can be seen from the figure that the structure of the compound is correct.

Embodiment 2

[0027] Weigh respectively 5mg (0.05mmol) of CuCl and 176.0mg (0.5mmol) of 1,3-di-p-ethylphenyldiyne into a 25-mL glass reaction tube with a cover, and replace the air in the reaction tube with nitrogen. Add 0.5mL of aniline in a nitrogen atmosphere, then seal the reaction tube, heat the reaction tube to 100°C in an oil bath, stir and keep it warm for 24 hours, and then cool to room temperature to obtain the target product 1-phenyl-2 provided by the present invention. 5-Di-p-ethylphenylpyrrole. Reaction result: the isolated target product 1-phenyl-2,5-di-p-ethylphenylpyrrole was weighed, and the isolated yield of the product was calculated to be 95%. image 3 and Figure 4 The hydrogen spectrum and carbon spectrum of the target product 1-phenyl-2,5-di-p-ethylphenylpyrrole prepared in this example are shown respectively. It can be seen from the figure that the structure of the compound is correct.

Embodiment 3

[0029] Weigh 5 mg (0.05 mmol) of CuCl and 178.0 mg (0.5 mmol) of 1,3-di-p-methoxyphenyldiyne into a 25-mL glass reaction tube with a cover, replace the air in the reaction tube with nitrogen, Add 0.5mL of aniline in a nitrogen atmosphere, then seal the reaction tube, heat the reaction tube to 100°C in an oil bath, stir and keep it warm for 24 hours, and then cool to room temperature to obtain the target product 1-phenyl-2 , 5-di-p-methoxyphenylpyrrole. Reaction result: the isolated target product 1-phenyl-2,5-di-p-methoxyphenylpyrrole was weighed, and the isolated yield of the product was calculated to be 92%.

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Abstract

The invention discloses a method for synthesizing substituted pyrrole, comprising the following steps: carrying out addition reaction on a catalyst and 1,3-conjugate diyne in the primary organic amine in an inert atmosphere to obtain the substituted pyrrole after the reaction is finished. In the method, the catalyst is at least one selected from CuC1, CuBr and CuI; the primary amine compound is aliphatic organic amine or aromatic organic amine; the 1,3-conjugate diyne is aromatic 1, 3-conjugate diyne or aliphatic 1, 3-conjugate diyne or 1,3-conjugate diyne crossed by the above two. The method of the invention adopts low-price, safe, easily obtained and simple cuprous compound as a catalyst, and has simple and moderate reaction condition; and the catalyst system shows that the substituted pyrrole is efficiently and high selectively synthesized by one-step method by the addition reaction of the 1,3-conjugate diyne and the primary amine.

Description

technical field [0001] The invention belongs to the technical field of catalytic synthesis of fine chemical products, and relates to a method for synthesizing a substituted pyrrole, in particular to a method for synthesizing a substituted pyrrole in one step through the cycloaddition reaction of a 1,3-conjugated diyne and a primary amine. Background technique [0002] Pyrrole and its derivatives are an important class of five-membered nitrogen-containing heterocyclic compounds. There are many macromolecular compounds containing pyrrole rings in nature. They are widely used in medicine, biology, food, pesticides, coatings, textiles, daily chemicals, papermaking It has important uses in the fields of photosensitive materials, polymer materials, etc. At the same time, various pyrrole monocyclic compounds containing substituents also have important uses in the fields of natural product chemistry, material chemistry, medicinal chemistry, and energy technology. Therefore, this Com...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D409/14C07D207/333C07D207/323C07D207/33C07D207/325
Inventor 华瑞茂郑庆伟
Owner TSINGHUA UNIV
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