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Method for primary amine guiding construction of 7-methyl-6-phenylindolo[1,2-a]quinoxaline

A technology of phenylindole and 2-a, which is applied in the field of primary amine-directed construction of 7-methyl-6-phenylindolo[1,2-a]quinoxaline, which can solve the difficult preparation of substrates , high reaction temperature and other problems, to achieve the effect of simple operation, simple operation and mild reaction conditions

Inactive Publication Date: 2019-04-16
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 primary amine guiding construction of 7-methyl-6-phenylindolo[1,2-a]quinoxaline
  • Method for primary amine guiding construction of 7-methyl-6-phenylindolo[1,2-a]quinoxaline
  • Method for primary amine guiding construction of 7-methyl-6-phenylindolo[1,2-a]quinoxaline

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] 0.2 mmol of 2-(3-methyl-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. Pure 7-methyl 6-phenylindolo[1,2-a]quinoxaline was obtained with a yield of 25%.

Embodiment 2

[0022] 0.2 mmol of 2-(3-methyl-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 7-methyl 6-phenylindolo[1,2-a]quinoxaline was obtained with a yield of 47%.

Embodiment 3

[0024] Add 0.2 mmol of 2-(3-methyl-1H-indol-1-yl)aniline, 0.01 mmol of palladium trifluoroacetate, 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 50:1. The pure 7-methyl 6-phenylindolo[1,2-a]quinoxaline was obtained with a yield of 36%.

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Abstract

The invention discloses a method for primary amine guiding construction of 7-methyl-6-phenylindolo[1,2-a]quinoxaline. In a reaction test tube, 2-(3-methyl-1H-indol-1-yl)aniline and benzoyl formic acidare added as raw materials, and after an acylation / cyclization reaction, the 7-methyl-6-phenylindolo[1,2-a]quinoxaline is obtained with the high yield. The primary amine guiding acylation / cyclizationreaction is achieved for the first time, consumption of alkali and other additives is avoided, raw materials needed by the reaction are cheap and easy to obtain, the conditions are mild, operation iseasy, the selectivity is single, the separation yield is high, industrial production is facilitated, and the development requirement for green and organic chemistry is met.

Description

technical field [0001] The invention relates to the technical field of pharmaceutical chemical synthesis, in particular to a method for constructing 7-methyl-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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