Method for constructing 2-fluorine-6-phenyl indolo[1,2-a] quinoxaline through primary amine guiding

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

Inactive Publication Date: 2019-03-22
GUILIN UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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-fluorine-6-phenyl indolo[1,2-a] quinoxaline through primary amine guiding
  • Method for constructing 2-fluorine-6-phenyl indolo[1,2-a] quinoxaline through primary amine guiding
  • Method for constructing 2-fluorine-6-phenyl indolo[1,2-a] quinoxaline through primary amine guiding

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] 0.2 mmol of 4-fluoro-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. Pure 2-fluoro-6-phenylindolo[1,2-a]quinoxaline was obtained with a yield of 27%.

Embodiment 2

[0022] 0.2 mmol of 4-fluoro-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. Pure 2-fluoro-6-phenylindolo[1,2-a]quinoxaline was obtained with a yield of 41%.

Embodiment 3

[0024] 0.2 mmol of 4-fluoro-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, 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 the crude product, which is finally separated and purified by column chromatography, and the column chromatography eluent used is a mixed solvent of petroleum ether:ethyl acetate with a volume ratio of 50:1. Pure 2-fluoro-6-phenylindolo[1,2-a]quinoxaline was obtained with a yield of 25%.

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Abstract

The invention discloses a method for constructing 2-fluorine-6-phenyl indolo[1,2-a] quinoxaline through primary amine guiding. The method comprises the following steps: adding 4-fluorine-2-(1H-indole-1-yl)phenylamine and benzoyl formic acid as the raw material in a reaction test tube, and preparing 2-fluorine-6-phenyl indolo[1,2-a] quinoxaline in high yield through acylation / cyclization reaction.The primary amine is used as a traceless guide base, and the step economy of the reaction is increased; the raw material required by the reaction is cheap and easy to obtain, the condition is mild andthe operation is simple, the selectivity is single, the separation efficiency is high, and the method is in favor of industrial production and conforms to the development demand of the green organicchemistry.

Description

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