Novel method for synthesizing indolo[1,2-a]quinoxaline derivative

A 2-a, quinoxaline technology, applied in the field of synthesizing indolo[1,2-a]quinoxaline derivatives, can solve the problem of poor economy and environmental friendliness, and poor substrate universality , low reactivity of aromatic hydrocarbons, etc., to achieve the effects of good substrate universality, easy operation, and simple and easy-to-obtain raw materials

Active Publication Date: 2020-04-10
GUILIN UNIVERSITY OF TECHNOLOGY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the organic reaction using acid chloride as an acyl source is usually completed through Friedel-Crafts acylation reaction, but there are many shortcomings in Friedel-Crafts acylation reaction: 1) The selectivity of Friedel-Crafts acylation reaction is not good, usually adjacent Both position substitution products and para substitution products exist; 2) electron-rich arenes react well, while electron-deficient arenes have low reactivity, which means that the substrate universality of Friedel-Crafts acylation reaction is not good; 3) Friedel-Crafts acylation reaction is often accompanied by the use of equivalent Lewis acid, which is not economical and environmentally friendly (K.Jing, Z.-Y.Li, G.-W.Wang, ACS Catal.2018,8,11875 -11881)

Method used

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  • Novel method for synthesizing indolo[1,2-a]quinoxaline derivative
  • Novel method for synthesizing indolo[1,2-a]quinoxaline derivative
  • Novel method for synthesizing indolo[1,2-a]quinoxaline derivative

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Experimental program
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Effect test

Embodiment 1

[0041] In the sealed tube, add 0.1 mmol of 2-(1H-indol-1-yl)aniline, 0.2 mmol of benzoyl chloride, 0.01 mmol of bis(dibenzylideneacetone) palladium, and 0.025 mmol of hexafluoroantimonic acid. Silver and 0.2 mmol of cesium pivalate, then add 1 ml of anhydrous toluene and 1,4-dioxane mixed solvent (the volume ratio is 1:1), argon protection, stirring at 130 ℃ After reacting for 24 hours, the reaction was stopped, cooled to room temperature and filtered. The filtrate was extracted 3 times with ethyl acetate. The organic phases were combined and dried over anhydrous magnesium sulfate, filtered, and rotary evaporated under reduced pressure to obtain the crude product, which was finally separated and purified by column chromatography The column chromatography eluent used is a mixed solvent of petroleum ether and ethyl acetate (petroleum ether: ethyl acetate = 100:1). The pure 6-phenylindolo[1,2-a]quinoxaline was obtained with a yield of 76%.

[0042] The hydrogen spectrum and carbon ...

Embodiment 2

[0049] In the sealed tube, add 0.1 mmol of 2-(1H-indol-1-yl)aniline, 0.2 mmol of 4-methylbenzoyl chloride, 0.01 mmol of bis(dibenzylideneacetone) palladium, and 0.025 mmol of Silver hexafluoroantimonate and millimoles of cesium pivalate, then add 1 ml of anhydrous toluene and 1,4-dioxane mixed solvent (the volume ratio is 1:1), argon protection, at 130℃ The reaction was stirred for 24 hours under the conditions, the reaction was stopped, cooled to room temperature and filtered, the filtrate was extracted 3 times with ethyl acetate, the organic phases were combined and dried over anhydrous magnesium sulfate, filtered, and rotary evaporated under reduced pressure to obtain the crude product, and finally passed through the column layer The column chromatography eluent is a mixed solvent of petroleum ether and ethyl acetate (petroleum ether: ethyl acetate = 100:1). The pure 6-(4-methylphenyl)indolo[1,2-a]quinoxaline was obtained with a yield of 80%.

[0050] The hydrogen spectrum an...

Embodiment 3

[0057] In the sealed tube, add 0.1 mmol of 2-(1H-indol-1-yl)aniline, 0.2 mmol of 4-ethylbenzoyl chloride, 0.01 mmol of bis(dibenzylideneacetone) palladium, and 0.025 mmol of Silver hexafluoroantimonate and millimoles of cesium pivalate, then add 1 ml of anhydrous toluene and 1,4-dioxane mixed solvent (the volume ratio is 1:1), argon protection, at 130℃ The reaction was stirred for 24 hours under the conditions, the reaction was stopped, cooled to room temperature and filtered, the filtrate was extracted 3 times with ethyl acetate, the organic phases were combined and dried over anhydrous magnesium sulfate, filtered, and rotary evaporated under reduced pressure to obtain the crude product, and finally passed through the column layer The column chromatography eluent is a mixed solvent of petroleum ether and ethyl acetate (petroleum ether: ethyl acetate = 100:1). The pure 6-(4-ethylphenyl)indolo[1,2-a]quinoxaline was obtained with a yield of 75%.

[0058] The hydrogen spectrum and ...

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Abstract

The invention discloses a novel method for synthesizing an indolo[1,2-a]quinoxaline derivative. The novel synthesis method comprises the following steps: adding a palladium catalyst, an indole compound, acyl chloride, an additive, alkali and a solvent into a glass reaction container, carrying out a reaction under stirring at 110-130 DEG C under the protection of argon, and separating and purifyinga crude reaction product so as to obtain an indolo[1,2-a]quinoxaline compound. According to the invention, a coupling reaction of primary amine-guided acyl chloride and an indole derivative is developed; a series of functionalized indolo[1,2-a]quinoxaline derivatives can be constructed through simple operation; and high step economy and atom economy are achieved. In addition, the reaction in thenovel method provided by the invention has the main advantages of simple and easily-available substrate, single selectivity, good functional group tolerance and high yield.

Description

Technical field [0001] The invention belongs to the field of organic synthetic chemistry, and specifically relates to a new method for synthesizing indolo[1,2-a]quinoxaline derivatives. Background technique [0002] Heterocyclic compounds are an important class of organic compounds, which are widely present in natural products, pharmacologically active molecules and functional materials. Therefore, the efficient and simple preparation method of heterocyclic compounds has always been a research hotspot and difficulty in the field of organic chemistry. With the vigorous development of organometallic chemistry, in recent years, research strategies assisted by transition metal catalytic guiding groups have provided efficient synthesis methods for the preparation of heterocyclic compounds. Compared with other methods, it has higher step economy and regional selectivity. In 2017, the Glorius research group reported the efficient cyclization reaction of imines catalyzed by manganese (Q...

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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