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Method for constructing 9-methoxyl-6-phenylindolo[1,2-a]quinoxaline through primary amine guidance

A technology of phenylindole and methoxy, which is applied in the field of pharmaceutical and chemical synthesis, can solve the problems of high reaction temperature and difficult substrate preparation, and achieve the effects of simple operation, high yield and high step economy

Inactive Publication Date: 2019-03-08
GUILIN UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

And in these known reactions, there are deficiencies such as reaction temperature is high, substrate is difficult to prepare, etc.

Method used

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  • Method for constructing 9-methoxyl-6-phenylindolo[1,2-a]quinoxaline through primary amine guidance
  • Method for constructing 9-methoxyl-6-phenylindolo[1,2-a]quinoxaline through primary amine guidance
  • Method for constructing 9-methoxyl-6-phenylindolo[1,2-a]quinoxaline through primary amine guidance

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Experimental program
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Effect test

Embodiment 1

[0020] Add 0.2 mmol of 2-(5-methoxy-1H-indol-1-yl) aniline, 0.01 mmol of palladium chloride, 0.4 mmol of potassium persulfate and 0.4 mmol of benzoylformic acid in the reaction tube . Then add 2 ml of 1,4-dioxane as a solvent, stir the reaction at 78°C for 12 hours, then stop the reaction, cool to room temperature and filter, and extract the filtrate three times with ethyl acetate, combine the organic phases and use 0.5 g Dry over anhydrous magnesium sulfate, filter, and rotary evaporate under reduced pressure to obtain a crude product, which is finally separated and purified by column chromatography, and the eluent used in column chromatography is a mixed solvent of petroleum ether:ethyl acetate with a volume ratio of 20:1. Pure 9-methoxy-6-phenylindolo[1,2-a]quinoxaline was obtained with a yield of 49%.

Embodiment 2

[0022] 0.2 mmol of 2-(5-methoxy-1H-indol-1-yl)aniline, 0.01 mmol of palladium acetate, 0.4 mmol of potassium persulfate and 0.4 mmol of benzoylformic acid were successively added into the reaction tube. Then add 2 ml of 1,4-dioxane as a solvent, stir the reaction at 78°C for 12 hours, then stop the reaction, cool to room temperature and filter, and extract the filtrate three times with ethyl acetate, combine the organic phases and use 0.5 g Dry over anhydrous magnesium sulfate, filter, and rotary evaporate under reduced pressure to obtain a crude product, which is finally separated and purified by column chromatography, and the eluent used in column chromatography is a mixed solvent of petroleum ether:ethyl acetate with a volume ratio of 20:1. Pure 9-methoxy-6-phenylindolo[1,2-a]quinoxaline was obtained with a yield of 63%.

Embodiment 3

[0024] Add 0.2 mmol of 2-(5-methoxy-1H-indol-1-yl) aniline, 0.01 mmol of palladium trifluoroacetate, 0.4 mmol of potassium persulfate and 0.4 mmol of benzoyl formic acid. Then add 2 ml of 1,4-dioxane as a solvent, stir the reaction at 78°C for 12 hours, then stop the reaction, cool to room temperature and filter, and extract the filtrate three times with ethyl acetate, combine the organic phases and use 0.5 g Dry over anhydrous magnesium sulfate, filter, and rotary evaporate under reduced pressure to obtain a crude product, which is finally separated and purified by column chromatography, and the eluent used in column chromatography is a mixed solvent of petroleum ether:ethyl acetate with a volume ratio of 20:1. Pure 9-methoxy-6-phenylindolo[1,2-a]quinoxaline was obtained with a yield of 52%.

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Abstract

The invention relates to a method for constructing 9-methoxyl-6-phenylindolo[1,2-a]quinoxaline through primary amine guidance. The method comprises the following steps: adding 2-(5-methoxyl-1H-indole-1-yl)aniline and benzoylformic acid into a reaction test tube as raw materials, and carrying out acylation / cyclization reaction to prepare the 9-methoxyl-6-phenylindolo[1,2-a]quinoxaline in a high-yield manner. According to the method provided by the invention, primary amine is used as a traceless guidance group and the economic efficiency of steps of the reaction is increased; the raw materials needed by the reaction are cheap and easy to obtain, conditions are moderate and the operation is simple, the selectivity is single and the separation yield is high; industrial production is facilitated and the development requirements of green organic chemistry are met.

Description

technical field [0001] The invention relates to the technical field of pharmaceutical chemical synthesis, in particular to a method for constructing 9-methoxy-6-phenylindolo[1,2-a]quinoxaline guided by a primary amine. Background technique [0002] In recent years, organometallic chemistry has achieved unprecedented development and has become an important means of constructing carbon-carbon bonds and carbon-heterobonds. Directing group-assisted C–H functionalization reactions have attracted extensive attention from scientists due to their good selectivity and reactivity. After decades of development, a series of nitrogen-containing directing groups have been successfully used in C-H functionalization reactions, including primary amines, pyridines, amides, imines, oximes, enamines and various nitrogen-containing heterocycles. It is worth noting that there are very few reports on the C-H functionalization reaction of primary amines as directing groups, because primary amines ...

Claims

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Application Information

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IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 蒋光彬王守才及方华
Owner GUILIN UNIVERSITY OF TECHNOLOGY
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