Method for constructing 2-chloro-6-phenylindolo[1,2-a]quinoxaline by primary amine directing

A technology of phenylindole and 2-a, which is applied in the field of primary amine-directed construction of 2-chloro-6-phenylindolo[1,2-a]quinoxaline, can solve the problem of high reaction temperature and bottom problems such as difficult preparation of materials, to achieve the effect of simple operation, simple operation and single selectivity

Inactive Publication Date: 2019-03-22
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 2-chloro-6-phenylindolo[1,2-a]quinoxaline by primary amine directing
  • Method for constructing 2-chloro-6-phenylindolo[1,2-a]quinoxaline by primary amine directing
  • Method for constructing 2-chloro-6-phenylindolo[1,2-a]quinoxaline by primary amine directing

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] 0.2 mmol of 4-chloro-2-(1H-indol-1-yl)aniline, 0.01 mmol of palladium chloride, 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 50:1. The pure 2-chloro-6-phenylindolo[1,2-a]quinoxaline was obtained with a yield of 40%.

Embodiment 2

[0022] 0.2 mmol of 4-chloro-2-(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 50:1. The pure 2-chloro-6-phenylindolo[1,2-a]quinoxaline was obtained with a yield of 52%.

Embodiment 3

[0024] 0.2 mmol of 4-chloro-2-(1H-indol-1-yl)aniline, 0.01 mmol of palladium trifluoroacetate, 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 50:1. The pure 2-chloro-6-phenylindolo[1,2-a]quinoxaline was obtained with a yield of 35%.

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Abstract

The invention discloses a method for constructing 2-chloro-6-phenylindolo[1,2-a]quinoxaline by primary amine directing. 4-chloro-2-(1H-indole-1-yl)aniline and benzoyl formic acid are added into a reaction tube and used as raw materials, and high-yield 2-chloro-6-phenylindolo[1,2-a]quinoxaline is obtained by acylation/cyclization reaction. According to the method, primary amine is used as a traceless directing group, and thus the economical efficiency of the reaction steps is increased; and the raw materials required for the reaction are cheap and easy to obtain, conditions are mild, the operation is simple, the selectivity is single and the separation yield is high, therefore, the method facilitates industrial production and is in line with the development needs of green organic chemistry.

Description

technical field [0001] The invention relates to the technical field of pharmaceutical chemical synthesis, in particular to a method for constructing 2-chloro-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 h...

Claims

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Application Information

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Patent Type & Authority Applications(China)
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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